DOCSLIB.ORG

Opening Kinetics of Oxazine Ring and Hydrogen Bonding Effects on Fast Polymerization Of

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Opening Kinetics of Oxazine Ring and Hydrogen Bonding Effects on Fast Polymerization Of UNDERSTANDING THE VIBRATIONAL STRUCTURE, RING- OPENING KINETICS OF OXAZINE RING AND HYDROGEN BONDING EFFECTS ON FAST POLYMERIZATION OF 1,3- BENZOXAZINES by LU HAN Submitted in partial fulfillment of the requirements for the degree of Doctor of Philosophy Dissertation Advisor: Dr. Hatsuo Ishida Department of Macromolecular Science and Engineering CASE WESTERN RESERVE UNIVERSITY May, 2018 CASE WESTERN RESERVE UNIVERSITY SCHOOL OF GRADUATE STUDIES We hereby approve the thesis/dissertation of Lu Han Candidate for the degree of Doctor of Philosophy. * Committee Chair Dr. Hatsuo Ishida Dr. Gary Wnek Dr. Lei Zhu Dr. Daniel Lacks Date of Defense Nov. 2nd, 2017 *We also certify that written approval has been obtained for any proprietary material contained therein. DEDICATION To my parents, Jianjun Han and Jinyan Zhang TABLES OF CONTENTS TABLE OF CONTENTS i LIST OF TABLES iv LIST OF SCHEMES v LIST OF FIGURES vi ACKNOWLEDGEMENTS xiii ABSTRACT xv CHAPTER 1: Introduction 1 1.1 Review of benzoxazine 2 1.2 Oxazine ring related modes 3 1.3 Intrinsic ring opening of oxazine ring 3 1.4 Hydrogen bonding in amide-containing benzoxazine 4 1.5 References 4 CHAPTER 2: Study of oxazine ring-related vibrational modes of benzoxazine monomers 8 2.1 Introduction 8 2.2 Experimental 13 i 2.3 Results and Discussion 25 2.4 Conclusions 51 2.5 References 51 CHAPTER 3: Investigation of intrinsic self-initiating thermal ring-opening polymerization of 1,3-benzoxazines 55 3.1 Introduction 56 3.2 Experimental 60 3.3 Results and Discussion 65 3.4 Conclusions 91 3.5 References 92 CHAPTER 4: Study of the effects of intramolecular and intermolecular hydrogen- bonding of amide-containing benzoxazines 96 4.1 Introduction 97 4.2 Experimental 99 4.3 Results and Discussion 102 4.4 Conclusions 120 4.5 References 120 ii CHAPTER 5: Conclusion 125 5.1 Oxazine ring related modes 126 5.2 Intrinsic ring opening of oxazine ring 126 5.3 Hydrogen bonding in amide-containing benzoxazine 126 SUPPORTING INFORMATION 128 iii LIST OF TABLES Table 2.1 Potential energy distribution for the oxazine ring-related modes of PH-a which is calculated using Gaussian 09 with B3LYP/6-31G** theory and basis and VEDA4 software. 43 Table 2.2 Frequency of the characteristic band in experimental FT-IR and Raman and theoretical model for PH-a, PH-a-phenol-d4, PH-a-2oxazine-d2, PH-a-4oxazine-d2, PH- 15 a-oxazine-d4, PH-d-a and PH-a- N. 46 Table 3.1 Elemental Analysis Results of PH-a. 71 Table 3.2 Weight of 4-methoxyphenol and PH-a of different phenolic content mixture sample. 72 Table 3.3 Phenolic content in each PH-a/4-metoxyphenol mixture and the specific weight of every sample studied by DSC. 73 Table 3.4 Polymerization temperature of mixture samples measured by DSC. 76 Table 4.1 Maxima of the N-H stretching absorption bands observed by FT-IR. Spectra were recorded in solution using CHCl3 as solvent. 107 Table 4.2 Examples of reported results on secondary amide N-H stretching band positions determined by FT-IR. 111 Table 4.3 Chemical shifts of the –O–CH2–N= and =N–CH2–Ar in CDCl3 and DMSO-d6 as solvent. 113 iv LIST OF SCHEMES Scheme 2.1 Synthesis scheme of all substituted benzoxazine. 26 Scheme 2.2 Synthesis scheme of isotopes of PH-x, PH-x-phenol-d4, PH-x-oxazine-d4 and PH-d-a. 30 Scheme 2.3 Synthesis scheme of isotopes of PH-x-2oxazine-d2 and PH-x-4oxazine-d2. 31 Scheme 3.1 Solvent-less PH-a synthesis. 65 Scheme 4.1. Synthesis of benzoxazine monomers PH-a, pHBA-a, and oHBA-a. 104 v LIST OF FIGURES Figure 2.1 Chemical structure of all-substituted benzoxazines. 10 Figure 2.2 Chemical structure of PH-a series. 12 Figure 2.3 Chemical structure of PH-t series. 12 Figure 2.4 Chemical structure of methyl group substituted benzoxazine series. 13 1 Figure 2.5 H-NMR spectra for (a)25DMR-h, (b)PG-a and (c)PG-anis in CDCl3 at room temperature. 27 Figure 2.6 Comparison of FT-IR spectra of all-substituted benzoxazine monomer (top) and its corresponding polymer obtained by heating the monomer at 180oC for 2 h (bottom): (a) 25DMR-h and its polymer; (b) PG-a and its polymer; (c) PG-anis and its polymer. 28 Figure 2.7 1H-NMR spectra for PH-a isotopes (left) and PH-t isotopes (right). (a) PH-a, (b) PH-a-phenol-d4, (c) PH-a-2oxazine-d2, (d) PH-a-4oxazine-d2, (e) PH-a-oxazine-d4, (f) PH-d-a, (g) PH-t, (h) PH-t-phenol-d4, (i) PH-t-2oxazine-d2, (j) PH-t-oxazine-d4 in CDCl3 at room temperature. 33 Figure 2.8 FT-IR spectra of PH-a isotopes (left) and PH-t isotopes (right). (a) PH-a, (b) PH-a-phenol-d4, (c) PH-a-2oxazine-d2, (d) PH-a-4oxazine-d2, (e) PH-a-oxazine-d4, (f) PH-d-a, (g) PH-t, (h) PH-t-phenol-d4, (i) PH-t-2oxazine-d2, (j) PH-t-oxazine-d4. 34 Figure 2.9 FT-IR spectra of (a) PH-a, (b) PH-a-15N. 36 vi 1 Figure 2.10 H-NMR spectra for PH-a-4oxazine and PH-a-2oxazine in CDCl3 at room temperature. 38 Figure 2.11 FT-IR spectra of oxazine ring substituted PH-a. (a) PH-a-4oxazine, (b) PH- a-2oxazine. 39 Figure 2.12 The crystal structure and optimized structure of PH-a. 40 Figure 2.13 Experimental and theoretical FT-IR results for PH-a. 41 Figure 2.14 Comparison of experimental FT-IR results and theoretical results for FT-IR spectra of PH-a isotopes (a) PH-a, (b) PH-a-phenol-d4, (c) PH-a-2oxazine-d2, (d) PH-a- 4oxazine-d2, (e) PH-a-oxazine-d4, (f) PH-d-a. 43 Figure 2.15 Characteristic band fitting of FT-IR spectrum of PH-a. 48 Figure 3.1 FT-IR spectrum of benzoxazine monomer, PH-a. 67 1 Figure 3.2 H NMR spectrum of PH-a. Satellites of each –CH2– peak corresponding to H2 and H4 can be better observed in the inset of the figure, which shows a close look near the baseline within the region between 4 and 6 ppm. Spectrum recorded at 25 °C, using DMSO- d6 as solvent. 68 Figure 3.3 a) DSC thermograms showing the change in the polymerization temperature of PH-a after successive recrystallization processes. b) Crystals of PH-a after all recrystallization processes. 70 Figure 3.4 DSC thermograms, region between 240 and 190 oC showing the exothermic polymerization peaks of different mixturesamples with increasing percentages of 4- methoxyphenol: (a) 0.00% of 4-methoxyphenol (pure PH-a), (b) 0.23 mol% of 4-methoxy- vii phenol, (c) 0.44 mol% of 4-methoxyphenol, (d) 0.56 mol% of 4-methoxyphenol, (e) 0.88 mol% of 4-methoxyphenol, and (f) 1.05mol% of 4-methoxyphenol. 75 Figure 3.5 Polymerization temperature as a function of the concentration of a phenol- containing compound (4-methoxypheonol). 77 Figure 3.6 DSC thermogram of PH-a from 30 to 300 °C. The endothermic peak at 59 °C is assigned to the melting while the exothermic one at 272 °C to the polymerization of PH- a. 79 Figure 3.7 Resonance structures of the unsubstituted benzoxazine PH-a. Structures in involving the aromatic ring that was adjacent to the oxazine ring (a) and the aniline moiety (b). 81 Figure 3.8 Simplified mechanisms for the polymerization of benzoxazines. a) The classically accepted thermally accelerated (or activated) polymerization mechanism, where in addition to heat impurities must participate in the initiation step; and b), thermal polymerization mechanism, induced only by heat. 83 Figure 3.9 Ring-chain tautomeric equilibrium of the unsubstituted benzoxazine PH-a. 84 Figure 3.10 Resonance structures of the chain-like tautomer of the unsubstituted benzoxazine PH-a involving the aromatic ring that was adjacent to the oxazine ring. 85 Figure 3.11 Plots to graphically calculate the activation energy (Ea) of the polymerization reaction of PH-a applying the Kissinger and Ozawa methods. In the plots, β is the constant heating rate and Tp is the maximum value of the exothermic polymerization peak. Linear viii regression obtained for each method are: R2 = 0.996 for the Kissinger method and R2 = 0.997 for the Ozawa method. 87 Figure 3.12 TGA thermogram of the highly purified poly(PH-a). 89 Figure 4.1 (a) 1H and (b) 13C NMR spectra of pHBA-a, (c) 1H and (d) 13C NMR spectra of oHBA-a. 105 Figure 4.2 FT-IR spectra showing the region between 3500 and 3380 cm-1 for (a) pHBA- a, and (b) oHBA-a. Spectra were recorded in solution at different concentrations using CHCl3 as solvent. 107 Figure 4.3 pHBA-a, and oHBA-a N-H stretching wavenumber vs. concentration. 109 Figure 4.4 1H NMR spectra of pHBA-a at different concentrations. All spectra were recorded at 25 °C using CDCl3 as solvent. 112 Figure 4.5 DSC thermograms comparing oHBA-a, pHBA-a with PH-a. 115 Figure 4.6 DSC thermograms comparing poly(PH-a) (blue), poly(pHBA-a) (red), and poly(oHBA-a) (black). 119 Figure S.1 NMR Spectrum of 25DMR-h 129 Figure S.2 NMR Spectrum of PG-a 130 Figure S.3 NMR Spectrum of PG-anis 131 Figure S.4 NMR Spectrum of PH-a 132 Figure S.5 NMR Spectrum of PH-a-phenol-d4 133 Figure S.6 NMR Spectrum of PH-a-2oxazine-d2 134 ix Figure S.7 NMR Spectrum of PH-a-4oxazine-d2 135 Figure S.8 NMR Spectrum of PH-a-oxazine-d4 136 Figure S.9 NMR Spectrum of PH-d-a 137 Figure S.10 NMR Spectrum of PH-t 138 Figure S.11 NMR Spectrum of PH-t-phenol-d4 139 Figure S.12 NMR Spectrum of PH-t-2oxazine-d2 140 Figure S.13 NMR Spectrum of PH-t-oxazine-d4 141 Figure S.14 NMR Spectrum of PH-a-4oxazine 142 Figure S.15 NMR Spectrum of PH-a-2oxazine 143 Figure S.16 FT-IR Spectrum of 25DMR-h 144 Figure S.17 FT-IR Spectrum of PG-a 145 Figure S.18 FT-IR Spectrum of PG-anis 146 Figure S.19 FT-IR Spectrum of PH-a 147 Figure S.20 FT-IR Spectrum of PH-a-phenol-d4 148 Figure S.21 FT-IR Spectrum of PH-a-2oxazine-d2 149 Figure S.22 FT-IR Spectrum of PH-a-4oxazine-d2 150 Figure S.23 FT-IR Spectrum of PH-a-oxazine-d4 151 Figure S.24 FT-IR Spectrum of PH-d-a 152 Figure S.25 FT-IR Spectrum of PH-t 153 x Figure S.26 FT-IR Spectrum of PH-t-phenol-d4
Load more

Recommended publications
  • United States Patent (10) Patent No.: US 8,969,514 B2 Shailubhai (45) Date of Patent: Mar
    USOO896.9514B2 (12) United States Patent (10) Patent No.: US 8,969,514 B2 Shailubhai (45) Date of Patent: Mar. 3, 2015 (54) AGONISTS OF GUANYLATECYCLASE 5,879.656 A 3, 1999 Waldman USEFUL FOR THE TREATMENT OF 36; A 6. 3: Watts tal HYPERCHOLESTEROLEMIA, 6,060,037- W - A 5, 2000 Waldmlegand et al. ATHEROSCLEROSIS, CORONARY HEART 6,235,782 B1 5/2001 NEW et al. DISEASE, GALLSTONE, OBESITY AND 7,041,786 B2 * 5/2006 Shailubhai et al. ........... 530.317 OTHER CARDOVASCULAR DISEASES 2002fOO78683 A1 6/2002 Katayama et al. 2002/O12817.6 A1 9/2002 Forssmann et al. (75) Inventor: Kunwar Shailubhai, Audubon, PA (US) 2003,2002/0143015 OO73628 A1 10/20024, 2003 ShaubhaiFryburg et al. 2005, OO16244 A1 1/2005 H 11 (73) Assignee: Synergy Pharmaceuticals, Inc., New 2005, OO32684 A1 2/2005 Syer York, NY (US) 2005/0267.197 A1 12/2005 Berlin 2006, OO86653 A1 4, 2006 St. Germain (*) Notice: Subject to any disclaimer, the term of this 299;s: A. 299; NS et al. patent is extended or adjusted under 35 2008/0137318 A1 6/2008 Rangarajetal.O U.S.C. 154(b) by 742 days. 2008. O151257 A1 6/2008 Yasuda et al. 2012/O196797 A1 8, 2012 Currie et al. (21) Appl. No.: 12/630,654 FOREIGN PATENT DOCUMENTS (22) Filed: Dec. 3, 2009 DE 19744O27 4f1999 (65) Prior Publication Data WO WO-8805306 T 1988 WO WO99,26567 A1 6, 1999 US 2010/O152118A1 Jun. 17, 2010 WO WO-0 125266 A1 4, 2001 WO WO-02062369 A2 8, 2002 Related U.S.
    [Show full text]
  • A Critical Study on Chemistry and Distribution of Phenolic Compounds in Plants, and Their Role in Human Health
    IOSR Journal of Environmental Science, Toxicology and Food Technology (IOSR-JESTFT) e-ISSN: 2319-2402,p- ISSN: 2319-2399. Volume. 1 Issue. 3, PP 57-60 www.iosrjournals.org A Critical Study on Chemistry and Distribution of Phenolic Compounds in Plants, and Their Role in Human Health Nisreen Husain1, Sunita Gupta2 1 (Department of Zoology, Govt. Dr. W.W. Patankar Girls’ PG. College, Durg (C.G.) 491001,India) email - [email protected] 2 (Department of Chemistry, Govt. Dr. W.W. Patankar Girls’ PG. College, Durg (C.G.) 491001,India) email - [email protected] Abstract: Phytochemicals are the secondary metabolites synthesized in different parts of the plants. They have the remarkable ability to influence various body processes and functions. So they are taken in the form of food supplements, tonics, dietary plants and medicines. Such natural products of the plants attribute to their therapeutic and medicinal values. Phenolic compounds are the most important group of bioactive constituents of the medicinal plants and human diet. Some of the important ones are simple phenols, phenolic acids, flavonoids and phenyl-propanoids. They act as antioxidants and free radical scavengers, and hence function to decrease oxidative stress and their harmful effects. Thus, phenols help in prevention and control of many dreadful diseases and early ageing. Phenols are also responsible for anti-inflammatory, anti-biotic and anti- septic properties. The unique molecular structure of these phytochemicals, with specific position of hydroxyl groups, owes to their powerful bioactivities. The present work reviews the critical study on the chemistry, distribution and role of some phenolic compounds in promoting health-benefits.
    [Show full text]
  • Clinical Practice Guidelines for Irritable Bowel Syndrome in Korea, 2017 Revised Edition
    J Neurogastroenterol Motil, Vol. 24 No. 2 April, 2018 pISSN: 2093-0879 eISSN: 2093-0887 https://doi.org/10.5056/jnm17145 JNM Journal of Neurogastroenterology and Motility Review Clinical Practice Guidelines for Irritable Bowel Syndrome in Korea, 2017 Revised Edition Kyung Ho Song,1,2 Hye-Kyung Jung,3* Hyun Jin Kim,4 Hoon Sup Koo,1 Yong Hwan Kwon,5 Hyun Duk Shin,6 Hyun Chul Lim,7 Jeong Eun Shin,6 Sung Eun Kim,8 Dae Hyeon Cho,9 Jeong Hwan Kim,10 Hyun Jung Kim11; and The Clinical Practice Guidelines Group Under the Korean Society of Neurogastroenterology and Motility 1Department of Internal Medicine, Konyang University College of Medicine, Daejeon, Korea; 2Konyang University Myunggok Medical Research Institute Daejeon, Korea; 3Department of Internal Medicine, Ewha Womans University School of Medicine, Seoul, Korea; 4Department of Internal Medicine, Gyeongsang National University, College of Medicine, Jinju, Korea; 5Department of Internal Medicine, Kyungpook National University, School of Medicine, Daegu, Korea; 6Department of Internal Medicine, Dankook University College of Medicine, Cheonan, Korea; 7Department of Internal Medicine, Yongin Severance Hospital, Yonsei University College of Medicine, Yongin, Korea; 8Department of Internal Medicine, Kosin University College of Medicine, Busan, Korea; 9Department of Internal Medicine, Sungkyunkwan University School of Medicine, Changwon, Korea; 10Department of Internal Medicine, Konkuk University School of Medicine, Seoul, Korea; and 11Department of Preventive Medicine, Korea University College of Medicine, Seoul, Korea In 2011, the Korean Society of Neurogastroenterology and Motility (KSNM) published clinical practice guidelines on the management of irritable bowel syndrome (IBS) based on a systematic review of the literature. The KSNM planned to update the clinical practice guidelines to support primary physicians, reduce the socioeconomic burden of IBS, and reflect advances in the pathophysiology and management of IBS.
    [Show full text]
  • A Four-Country Comparison of Healthcare Systems, Implementation
    Neurogastroenterology & Motility Neurogastroenterol Motil (2014) 26, 1368–1385 doi: 10.1111/nmo.12402 REVIEW ARTICLE A four-country comparison of healthcare systems, implementation of diagnostic criteria, and treatment availability for functional gastrointestinal disorders A report of the Rome Foundation Working Team on cross-cultural, multinational research M. SCHMULSON,* E. CORAZZIARI,† U. C. GHOSHAL,‡ S.-J. MYUNG,§ C. D. GERSON,¶ E. M. M. QUIGLEY,** K.-A. GWEE†† & A. D. SPERBER‡‡ *Laboratorio de Hıgado, Pancreas y Motilidad (HIPAM)-Department of Experimental Medicine, Faculty of Medicine-Universidad Nacional Autonoma de Mexico (UNAM). Hospital General de Mexico, Mexico City, Mexico †Gastroenterologia A, Department of Internal Medicine and Medical Specialties, University La Sapienza, Rome, Italy ‡Department of Gastroenterology, Sanjay Gandhi Postgraduate Institute of Medical Science, Lucknow, India §Department of Gastroenterology, University of Ulsan College of Medicine, Asan Medical Center, Seoul, Korea ¶Division of Gastroenterology, Mount Sinai School of Medicine, New York, NY, USA **Division of Gastroenterology and Hepatology, Houston Methodist Hospital and Weill Cornell Medical College, Houston, TX, USA ††Department of Medicine, Yong Loo Lin School of Medicine, National University of Singapore, Singapore, Singapore ‡‡Faculty of Health Sciences, Ben-Gurion University of the Negev, Beer-Sheva, Israel Key Messages • This report identified seven key issues related to healthcare provision that may impact how patients with FGIDs are investigated, diagnosed and managed. • Variations in healthcare provision around the world in patients with FGIDs have not been reviewed. • We compared four countries that are geographically and culturally diverse, and exhibit differences in the healthcare coverage provided to their population: Italy, South Korea, India and Mexico. • Since there is a paucity of publications relating to the issues covered in this report, some of the findings are based on the authors’ personal perspectives, press reports and other published sources.
    [Show full text]
  • The International Pharmacopoeia
    The International Pharmacopoeia THIRD EDITION Pharmacopoea internationalis Editio tertia Volume 4 Tests, methods, and general requirements Quality specifications for pharmaceutical substances, excipients, and dosage forms World Health Organization Geneva 1994 WHO Library Cataloguing in Publication Data The International Pharmacopoeia.- 3rd ed. Contents: v. 4. Tests, methods, and general requirements 1. Drugs -analysis 2. Drugs -standards ISBN 92 4 154462 7 (NLM Classification: QV 25) The World Health Organization welcomes requests for permission to reproduce or translate its publica- tions, in part or in full. Applications and enquiries should be addressed to the Of£ice of Publications, World Health Organization, Geneva, Switzerland, which will be glad to provide the latest information on any changes made to the text, plans for new editions, and reprints and translations already available. O World Health Organization, 1994 Publications of the World Health Organization enjoy copyright protection in accordance with the provi- sions of Protocol 2 of the Universal Copyright Convention. All rights reserved. The designations employed and the presentation of the material in this publication do not imply the expression of any opinion whatsoever on the part of the Secretariat of the World Health Organization concerning the legal status of any country, territory, city or area or of its authorities, or concerning the delimitation of its frontiers or boundaries. The mention of specific companies or of certain manufacturers' products does not imply that they are endorsed or recommended by the World Health Organization in preference to others of a similar nature that are not mentioned. Errors and omissions excepted, the names of proprietary products are distin- guished by initial capital letters.
    [Show full text]
  • Treatment for Acute Pain: an Evidence Map Technical Brief Number 33
    Technical Brief Number 33 R Treatment for Acute Pain: An Evidence Map Technical Brief Number 33 Treatment for Acute Pain: An Evidence Map Prepared for: Agency for Healthcare Research and Quality U.S. Department of Health and Human Services 5600 Fishers Lane Rockville, MD 20857 www.ahrq.gov Contract No. 290-2015-0000-81 Prepared by: Minnesota Evidence-based Practice Center Minneapolis, MN Investigators: Michelle Brasure, Ph.D., M.S.P.H., M.L.I.S. Victoria A. Nelson, M.Sc. Shellina Scheiner, PharmD, B.C.G.P. Mary L. Forte, Ph.D., D.C. Mary Butler, Ph.D., M.B.A. Sanket Nagarkar, D.D.S., M.P.H. Jayati Saha, Ph.D. Timothy J. Wilt, M.D., M.P.H. AHRQ Publication No. 19(20)-EHC022-EF October 2019 Key Messages Purpose of review The purpose of this evidence map is to provide a high-level overview of the current guidelines and systematic reviews on pharmacologic and nonpharmacologic treatments for acute pain. We map the evidence for several acute pain conditions including postoperative pain, dental pain, neck pain, back pain, renal colic, acute migraine, and sickle cell crisis. Improved understanding of the interventions studied for each of these acute pain conditions will provide insight on which topics are ready for comprehensive comparative effectiveness review. Key messages • Few systematic reviews provide a comprehensive rigorous assessment of all potential interventions, including nondrug interventions, to treat pain attributable to each acute pain condition. Acute pain conditions that may need a comprehensive systematic review or overview of systematic reviews include postoperative postdischarge pain, acute back pain, acute neck pain, renal colic, and acute migraine.
    [Show full text]
  • Phenolic Compounds and Uses in Fruit Growing A,B Melekber SULUSOGLU * Akocaeli University, Arslanbey Agricultural Vocational School, TR-41285, Kocaeli/Turkey
    Turkish Journal of Agricultural and Natural Sciences Special Issue: 1, 2014 TÜRK TURKISH TARIM ve DOĞA JOURNAL of AGRICULTURAL BİLİMLERİ DERGİSİ and NATURAL SCIENCES www.turkjans.com Phenolic Compounds and Uses in Fruit Growing a,b Melekber SULUSOGLU * aKocaeli University, Arslanbey Agricultural Vocational School, TR-41285, Kocaeli/Turkey. bKocaeli University, Graduate School of Natural and Applied Sciences, Department of Horticulture, TR-41380, Kocaeli/Turkey *Corresponding author: [email protected] Abstract Phenolic compounds are a class of chemical compounds in organic chemistry which consist of a hydroxyl group directly bonded to an aromatic hydrocarbon group. Phenolic compounds find in cell wall structures and play a major role in the growth regulation of plant as an internal physiological regulators or chemical messengers. They are used in the fruit growing field. They are related with defending system against pathogens and stress. They increase the success of tissue culture; can be helpful to identification of fruit cultivars, to determination of graft compatibility and identification of vigor of trees. They are also important because of their contribution to the sensory quality of fruits during the technological processes. In this review, the simple classification was given for these compounds and uses in the agricultural field were described. Key words: Phenolic compounds, fruit quality, fruit growing, cultivar identification, grafting, tree vigor Fenolik Bileşikler ve Meyve Yetiştiriciliğinde Kullanımı Özet Aromatik hidrokarbon grubuna bağlı bir hidroksil grubu içeren fenolik bileşikler organik kimyanın bir sınıfıdır. Fenolik bileşikler hücre duvarı yapısında bulunmakta ve içsel bir fizyolojik düzenleyici veya kimyasal haberci olarak bitki büyümesinin organizasyonunda önemli rol oynamaktadır. Meyve yetiştiriciliği alanında kullanılmaktadır.
    [Show full text]
  • 2015.09 IBS Drug Class Review.Pdf
    Drug Class Review Agents Indicated in the Treatment of Irritable Bowel Syndrome 56:92 GI Drugs, Miscellaneous Alosetron (Lotronex®) Eluxadoline (Viberzi®) Linaclotide (Linzess®) Lubiprostone (Amitiza®) Tegaserod (Zelnorm®) Final Report September 2015 Review prepared by: Melissa Archer, PharmD, Clinical Pharmacist Irene Pan, PharmD Candidate 2016 Chelsey Hancock, PharmD Candidate 2016 Carin Steinvoort, PharmD, Clinical Pharmacist Gary Oderda, PharmD, MPH, Professor University of Utah College of Pharmacy Copyright © 2015 by University of Utah College of Pharmacy Salt Lake City, Utah. All rights reserved. 1 Table of Contents Executive Summary ......................................................................................................................... 3 Introduction .................................................................................................................................... 4 Table 1. Comparison of the Agents Indicated in the Treatment of IBS ................................. 5 Disease Overview ........................................................................................................................ 6 Table 2. Summary of IBS Treatment Options ........................................................................ 8 Table 3. IBS Disease Staging System .................................................................................... 11 Table 4. Most Current Clinical Practice Guidelines for the Treatment of IBS ..................... 13 Pharmacology ..............................................................................................................................
    [Show full text]
  • Effects of Intravenous Hyoscine Butylbromide on Labour Outcome and Its Safety Among Parturients in Lautech Teaching Hospital Ogbomoso, Nigeria
    DISSERTATION TITLE: EFFECTS OF INTRAVENOUS HYOSCINE BUTYLBROMIDE ON LABOUR OUTCOME AND ITS SAFETY AMONG PARTURIENTS IN LAUTECH TEACHING HOSPITAL OGBOMOSO, NIGERIA. INSTITUTION DEPARTMENT OF OBSTETRICS AND GYNAECOLOGY, LADOKE AKINTOLA UNIVERSITY OF TECHNOLOGY TEACHING HOSPITAL, OGBOMOSO. INVESTIGATOR DR TAIWO OLUFIKOLA AKINBILE DISSERTATION SUBMITTED IN PARTIAL FULFILLMENT OF THE PART II (FINAL) FELLOWSHIP EXAMINATION OF THE NATIONAL POSTGRADUATE MEDICAL COLLEGE OF NIGERIA MAY, 2016. 1 DECLARATION I, Dr Taiwo Olufikola AKINBILE, hereby declare that this dissertation is original and it has not been presented to any other College for a Fellowship nor has it been submitted elsewhere for publication. Signature Date 2 TABLE OF CONTENTS Pages Title Page i Declaration ii Table of Contents iii List of Tables iv List of Figures v List of Acronyms and Abbreviations vi Certification viii Abstract ix 1. Introduction 1 2. Literature Review 4 3. Justification of the Proposed Study 12 4. Objectives 14 5. Methodology 15 6. Result 23 7. Discussion 37 References 43 Appendix I (Information on the Study Procedure to Participants) 50 Appendix II (Consent Form) 51 Appendix III (Proforma) 52 3 LIST OF TABLES Pages Table 1: Socio-Demographic distribution among respondents 23 Table 2: Obstetric history among respondents in the study groups 25 Table 3: Pattern of First stage of labour among respondents in the study 26 groups Table 4: Indication for Caesarean delivery among respondents that had 29 caesarean delivery in the study groups Table 5: Pattern of Second
    [Show full text]
  • Spectrophotometric Determination of Metoclopramide Hydrochloride in Bulk and Pharmaceutical Preparations by Diazotization-Coupling Reaction
    International Journal of Pharmacy and Pharmaceutical Sciences Academic Sciences ISSN- 0975-1491 Vol 5, Suppl 3, 2013 Research Article SPECTROPHOTOMETRIC DETERMINATION OF METOCLOPRAMIDE HYDROCHLORIDE IN BULK AND PHARMACEUTICAL PREPARATIONS BY DIAZOTIZATION-COUPLING REACTION AYMEN ABDULRASOOL JAWAD1, KASIM HASSAN KADHIM2 1Pharmaceutical Chemistry Department, College of Pharmacy, Kufa University, 2Chemistry Department, College of Sciences, Babylon University, Babylon, Iraq. Email: [email protected] Received: 24 May 2013, Revised and Accepted: 16 Jun 2013 ABSTRACT Objective: Develop a simple, rapid, sensitive, selective, and accurate method for the spectrophotometric determination of metoclopramide hydrochloride (MCP-HCl) in bulk and dosage forms. Methods: The method is based on diazotization of primary amine group of (MCP-HCl) with sodium nitrite and hydrochloric acid followed by coupling with 2,5-dimethoxyaniline (DMA) in aqueous mildly acidic medium to form a stable orange azo dye, showed a maximum absorption at 486 nm. Results: Beer's law was obeyed over the concentration range of 0.1-12 ppm with a molar absorptivity 4.55×104 L.mol-1.cm-1. Sandell’s sensitivity, limit of detection (LOD), and limit of quantification (LOQ) are 0.008 μg.cm-2, 0.016 ppm, and 0.054 ppm respectively, the recoveries range 99.15- 100.80%. Conclusions: The method has been successfully applied to the determination of (MCP-HCl) in its pharmaceutical preparations tablet, syrup, injection and drop with very good recoveries. Keywords: Spectrophotometric; Metoclopramide hydrochloride; Diazotization-coupling; 2,5-dimethoxyaniline; Pharmaceutical preparations INTRODUCTION aqueous solution 0.01M. Hydrochloric acid (BDH) aqueous solution 1M. Sulfamic acid (BDH) aqueous solution 0.2 M. 2,5- Metoclopramide Hydrochloride MCP-HCl is a white or almost white, dimethoxyaniline (Sigma-Aldrich) 0.01 M prepared using absolute crystalline powder which is very soluble in water.
    [Show full text]
  • Analysis of Naturally Occurring Phenolic Compounds in Aromatic Plants by RP-HPLC Coupled to Diode Array Detector (DAD) and GC-MS After Silylation
    Foods 2013, 2, 90-99; doi:10.3390/foods2010090 OPEN ACCESS foods ISSN 2304-8158 www.mdpi.com/journal/foods Article Analysis of Naturally Occurring Phenolic Compounds in Aromatic Plants by RP-HPLC Coupled to Diode Array Detector (DAD) and GC-MS after Silylation Charalampos Proestos 1,†,* and Michael Komaitis 2,† 1 Laboratory of Food Chemistry, Department of Chemistry, National and Kapodistrian University of Athens, 15771, Athens, Greece 2 Laboratory of Food Chemistry and Analysis, Department of Food Science and Technology, Agricultural University of Athens, 11855, Athens, Greece; E-Mail: [email protected] † These authors contributed equally to this work. * Author to whom correspondence should be addressed; E-Mail: [email protected]; Tel.: +30-210-727-4160 (ext. 160); Fax: +30-210-727-4476. Received: 6 February 2013; in revised form: 4 March 2013 / Accepted: 5 March 2013 / Published: 13 March 2013 Abstract: The following aromatic plants of Greek origin, Origanum dictamnus (dictamus), Eucalyptus globulus (eucalyptus), Origanum vulgare L. (oregano), Mellisa officinalis L. (balm mint) and Sideritis cretica (mountain tea), were examined for the content of phenolic substances. Reversed phase HPLC coupled to diode array detector (DAD) was used for the analysis of the plant extracts. The gas chromatography-mass spectrometry method (GC-MS) was also used for identification of phenolic compounds after silylation. The most abundant phenolic acids were: gallic acid (1.5–2.6 mg/100 g dry sample), ferulic acid (0.34–6.9 mg/100 g dry sample) and caffeic acid (1.0–13.8 mg/100 g dry sample). (+)-Catechin and (−)-epicatechin were the main flavonoids identified in oregano and mountain tea.
    [Show full text]
  • Effect of Antispasmodic Agents for the Treatment of Irritable Bowel Syndrome
    PHARMACOTHERAPEUTICS pISSN 1975-8456 / eISSN 2093-5951 J Korean Med Assoc 2018 July; 61(7):428-434 https://doi.org/10.5124/jkma.2018.61.7.428 과민성 장증후군 치료에서 진경제의 효과 이 상 헌ㆍ지 삼 룡 | 인제대학교 의과대학 부산백병원 내과 Effect of antispasmodic agents for the treatment of irritable bowel syndrome Sang Heon Lee, MD · Sam Ryong Jee, MD Department of Internal Medicine, Busan Paik Hospital, Inje University College of Medicine, Busan, Korea Antispasmodics are effective in reducing abdominal pain and controlling spasm. Irritable bowel syndrome (IBS) patients have characteristic key factors such as intestinal motility disorder and visceral hypersensitivity. So antispasmodics have been used in the treatment of IBS for decades. Mebeverine blocks intestinal peristalsis but are not significantly better than placebo. Alverine citrate combined with simethicone is effective treatment option in IBS. Otilonium and pinaverium bromide are poorly absorbed agents, so they have mostly local effect with minimal systemic adverse events. Phloroglucinol controls acute exacerbation of abdominal pain effectively. Tiropramide reduce abdominal discomfort without serious adverse events. Fenoverine control spasm in spastic colon but does not affect normal contraction. Trimebutine have dual actions that it inhibits hyperactive colon and activates hypomotile colon. Each drug has advantages and disadvantages. Antispasmodics are considered as the first treatment option of pain-dominant IBS. Key Words: Parasympatholytics; Abdominal pain; Irritable bowel syndrome 서론 2005년 Cochrane 문헌고찰에서 일부 진경제는 복통과 전 반적인 증상 호전에 효과가 있다고 하였는데 약한 증거수 과민성 장증후군은 이전에는 ‘경련성 대장’이라고 불리 준이었다[4]. 2006년 유럽에서 시행한 체계적 문헌고찰에 었다. 그 뜻은 경련이 증상을 일으킨다는 뜻이다[1]. 지난 수 서는 9개의 위약군대조시험들이 표준화된 진단기준이 결여 십 년 동안 과민성 장증후군 환자에게 진경제를 사용하고 있 되어 있다는 제한점을 발견하였다[5].
    [Show full text]