DOCSLIB.ORG

Synthesis of Imidazole-Based Medicinal Molecules Utilizing the Van Leusen Imidazole Synthesis

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Synthesis of Imidazole-Based Medicinal Molecules Utilizing the Van Leusen Imidazole Synthesis pharmaceuticals Review Synthesis of Imidazole-Based Medicinal Molecules Utilizing the van Leusen Imidazole Synthesis Xunan Zheng 1,2, Zhengning Ma 1,3 and Dawei Zhang 1,* 1 College of Chemistry, Jilin University, Changchun 130012, China; [email protected] (X.Z.); [email protected] (Z.M.) 2 College of Plant Science, Jilin University, Changchun 130062, China 3 Key Laboratory of Combinatorial Biosynthesis and Drug Discovery (Ministry of Education), School of Pharmaceutical Sciences, Wuhan University, Wuhan 430071, China * Correspondence: [email protected]; Tel.: +86-431-8783-6471 Received: 10 February 2020; Accepted: 1 March 2020; Published: 3 March 2020 Abstract: Imidazole and its derivatives are one of the most vital and universal heterocycles in medicinal chemistry. Owing to their special structural features, these compounds exhibit a widespread spectrum of significant pharmacological or biological activities, and are widely researched and applied by pharmaceutical companies for drug discovery. The van Leusen reaction based on tosylmethylisocyanides (TosMICs) is one of the most appropriate strategies to synthetize imidazole-based medicinal molecules, which has been increasingly developed on account of its advantages. In this review, we summarize the recent developments of the chemical synthesis and bioactivity of imidazole-containing medicinal small molecules, utilizing the van Leusen imidazole synthesis from 1977. Keywords: van Leusen; TosMICs; imidazole; synthesis 1. Introduction Imidazole ring, which is widely found in natural products and medical molecules, is one of the most prominent, five-membered, nitrogen-containing, heterocyclic scaffolds. Furthermore, imidazole-based heterocyclic compounds, which possess a vital position in medicinal chemistry, have been playing a central role in the treatment of numerous types of diseases, and new derivatives for medicinal use are being energetically developed worldwide [1–5]. Due to the peculiar structural characteristic of imidazole scaffold with a worthy electron-rich feature, it is advantageous for imidazole groups to combine with various receptors and enzymes in biological systems, through diverse weak interactions, thereby showing a variety of biological activities. At present, a legion of imidazole-containing compounds with high a medical potential as a clinical drug have been widely used to treat diverse types of illnesses, such as antibacterial [6,7], antifungal [8,9], anti-inflammatory [10,11], antiviral [12,13], anti-parasitic [14,15], anticancer [16,17], antihistaminic [18,19], and enzyme inhibition [20,21]. Imidazole and its derivatives encompass a vast range of medical activities, as shown in the following Table1. Pharmaceuticals 2020, 13, 37; doi:10.3390/ph13030037 www.mdpi.com/journal/pharmaceuticals Pharmaceuticals 2020, 13, 37 2 of 19 PharmaceuticalsPharmaceuticals 2020 20, 1320, ,x 13 FOR, x FOR PEER PEER REVIEW REVIEW 2 of 219 of 19 Pharmaceuticals 2020, 13, x FOR PEER REVIEW 2 of 19 PharmaceuticalsPharmaceuticals 20202020 20,, 131320,, ,,xx 13 FORFOR,, xx FORFOR PEERPEER PEERPEER REVIEWREVIEW REVIEWREVIEW 22 ofof 2 1919 of 19 TabTable 1.le Various 1. Various pharmacological pharmacological activities activities and andchemical chemical structures structures of imidazole of imidazole-based-based molecules molecules. Table 1.TabVariousle 1. Various pharmacological pharmacological activities activities and and chemical structures structures of imidazole of imidazole-based-based molecules molecules.. TabTablele 1.1.le Various 1. Various pharmacological pharmacological activities activities and andchemical chemical structures structures of imidazoleimidazole of imidazoleimidazole--based-based molecules molecules.. .. PharmacologicalPharmacological Activities Activities ChemicalChemical Structures Structures PharmacologicalPharmacological Activities Activities Chemical Chemical Structures Structures PharmacologicalPharmacological Activities Activities A A ChemicalChemical Structurestructures Structures Cl Cl PharmacologicalPharmacological Activities Activities A ChemicalChemical Structures Structures Cl A A Clll Cll 1 1 OH OH 1 OH Cl Cl 2 2 1 1 N NOH OH 2 1 1 O2N O2N COHH3 COHH3 Cl O N N CH Clll Cll 22 2 AntibacterialAntibacterial 2 N N 3 HN HNN ClN Cl O22N O2N N CNH33 CH3 Antibacterial 2 2 N 3 3 HN N AntibacterialAntibacterialAntibacterial HN HNN N AntibacterialAntibacterial MetroMneiNdtraoznoiNdleazole HN HNN N Metronidazole MeettrrMoonneiiidttdrraoaznzooiidllleeazolle 1 1 2 2 1 2 N 11 N 1 N 22N 2 N N N N N N NN NN NN NN N N N ONH OH N ONH N N OH OH OH OH 4 4 AntifungalAntifungal 3 3 4 AntifungalAntifungal 3 44 4 AntifungalAntifungal 3 3 PhenPhetheynliemthidyalizmoildeazole BifonBiazfonleazole Phenethylimidazole Bifonazole eenneet enemt aazmzooeeazo e oonnaazzooneeazo e PhenPhetthheyyn3lililiemtthiiiddya3lilizmoiildlleazolle Biffon4Biazffoonlll4eazolle 3 4 6 6 5 5 N 33N 3 44 4 O O 6 5 Cl CNl N N O 6 6 5 5 Cl N N N O O Clll Cll N N N N N N NNON O N N N N N N NO F F N NO O AntiAnti-inflammatory-inflammatory F Anti-inflammatory F F SO2NHSO22NH2 Anti-inflammatoryAntiAnti--inflammatoryinflammatory-inflammatory H COH CO SO NH 3 3 SO2 NHSO2 NH H3CO m coxm xSO22NHSO222NH2 H3C H3C7 7 H COH COCi iCi ibico ib H C H33COH3COCimicoxib 3 7 x x H 3C H3C7 7 Ciiimiii5coCcoiimxiiibiibco5 xiib 33 3C77 6 77 6 5 6 H3C 5H5 3C 5 66 6 CH3 CH3 A A 7 7 H3C H C H CH3 A 7 H33C H3CCH CH A A 7 7 CH33 CH3 A A 7 7 N N S S N S N N O O N NN SN S N O O S S Cl Cl N N O H N H N N Cl NN SN S O O 2 2O N N NS HN HN H2N O O N N Clll Cll N 8 8 AntiviralAntiviral H N H NO O N NS HNS 8 Antiviral H22N H2ON O N N HN HN Antiviral O Cl Cl HN HN 88 8 AntiviralAntiviral Cl O O O2N O2N N N Clll Cll O N N 2 O22N O2N CNapraCvNairpirnaevirine 2 2 Capravirine CaaprrCaavaviprrirrnnaeevirrine 8 8 C p C7aiipii a7 ii ii e 8 7 88 8 77 7 N8 N8 N N N 10 10 O N O NN N 10 9 9 2 2N 10 10 9 O2N N N 10 10 O 2N O2NN N 9 9 O22N O2N H3C H3C N N AntiparasiticAntiparasitic H3C N N N Antiparasitic H C H C N N AntiparasiticAntiparasiticAntiparasitic H33CNH3C N N N N Antiparasitic N NN O O O2N O2N O O N N N NimoNiramzoolerazole O2 N O N morazo eO O O22N O2N Ni l 9 9 Nimoo1Nirr0aamzzooo1lllrere0azolle 9 10 N N 99 9 O O 1100 10 N O NH2 NH2 NO2 NO 12 12 11 N N 2 O ONH2 11 N NNO2 NH NH CH CH 12 11 NO NO NH22NH2 3 3 12 12 N NO22NO2 N N CH 12 12 11 11 N N O O N N NNNN 3N N N CH33CH3 O CH3 CH3 N N N N N 3 3 N NN NN NNCHN3 CH3 AnticancerAnticancer O CHO3 NH N NNNN N Anticancer OH OH CH CH H CH3 CH33CH3 HN N CH CH AnticancerAnticancerAnticancer OH N N CH33CH3 Anticancer OH OH H H MiOsoH nMiOidHsoaznoidleazole DacaDrbacaazirnbeazine Misonidazole Dacarbazine MisosoMin11niiiddsoaazzn11ooiidllleeazolle DacaacaD12rrbacabaazzi12irirnnbeeaziine 11 D 12Db i b i 1111a 11a 1212 12 O O 14 14 a O 14 13 13 aa a 1414 14 13 a a O O 13 13 N CNH3 CH3 13 13 N CH3 N N N CNH CH AntihistaminicAntihistaminic N N CNH33 CH3 N N O O N N N O Antihistaminic N N N N O O AntihistaminicAntihistaminicAntihistaminic NH N N O O He me N N rox arnox an HN MN thiMethipimp epip NH H Cip Cifp if H MHethimepip Ciproxifan Pharmaceuticals 2020, 13, x FOR PEER REVIEW H He mee me HN N rrooxx aaronnx an 3 of 19 Pharmaceuticals 2020, 13, x FOR PEER REVIEW Metthihi1M3meetthipp1iimi3ppepiip H H Ciiippr1oC4xiiiipffar1on4xiiffan 3 of 19 13 H H 14 1133 13 1144 14 A CH3 15 A CH3 15 16 N 16 N N N N N N N Enzyme inhibitor N O EnzymeEnzyme inhibitor inhibitor N O NO2 NO2 15 16 15 16 OwingOwing to the to thesignificant significant pharmacological pharmacological or biologicalor biological activities activities and and the theenormous enormous medicinal medicinal valuevalue of imidazole of imidazole-based-based molecul molecules, thees, thesynthes synthesis ofi sthe of theimidazole imidazole-skeleton-skeleton small small molecul molecule haes habeens been paidpaid attention attention to by to pharmaceuticalby pharmaceutical chemists chemists and and organic organic synthesis synthesis researchers researchers. However. However, there, there is is stillstill a need a need for afor simple a simple and and efficient efficient way way to construct to construct the theimidazole imidazole heterocyclic heterocyclic skeleton skeleton. In .recent In recent decades,decades, there there have have been been numerous numerous classical classical strategies strategies for forsynthesizing synthesizing this th ringis ring compound compound in the in the laboratorylaboratory, including, including van van Leusen Leusen imidazole imidazole synthesis synthesis [22], [22], Debus Debus-Radziszewski-Radziszewski imidazole imidazole synthesis synthesis [23],[23], Wallach Wallach imidazole imidazole synthesis synthesis [24] [24], etc., etc.Among Among these these synthetic synthetic strategies, strategies, it is it well is well-known-known that that the thevan van Leusen Leusen imidazole imidazole synthesis synthesis based based on TosMICson TosMICs, which, which is the is thecycloaddition cycloaddition reaction reaction, is one, is one of of the themost most convenient convenient and and attractive attractive protocols protocols for thefor thepreparation preparation of imidazole of imidazole-based-based small small molecules molecules, , duedue to its to excellentits excellent advantages advantages like like simple simple manipulation manipulation, easily, easily obta obtainedined raw raw materials materials and and a wide a wide range of substrates, which has been developed rapidly in the past decades (Scheme 1). range of substrates, which has been developed rapidly in the past decades (Scheme 1). R1 3 2 R1 R (H) 3 Base R 2 1 2 + R (H) Base NR R CH 1NR 2 + N 3 R CH NR Tos NC R (H) 3 Tos NC N R (H) N Scheme 1.
Load more

Recommended publications
  • Transport of Dangerous Goods
    ST/SG/AC.10/1/Rev.16 (Vol.I) Recommendations on the TRANSPORT OF DANGEROUS GOODS Model Regulations Volume I Sixteenth revised edition UNITED NATIONS New York and Geneva, 2009 NOTE 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 United Nations concerning the legal status of any country, territory, city or area, or of its authorities, or concerning the delimitation of its frontiers or boundaries. ST/SG/AC.10/1/Rev.16 (Vol.I) Copyright © United Nations, 2009 All rights reserved. No part of this publication may, for sales purposes, be reproduced, stored in a retrieval system or transmitted in any form or by any means, electronic, electrostatic, magnetic tape, mechanical, photocopying or otherwise, without prior permission in writing from the United Nations. UNITED NATIONS Sales No. E.09.VIII.2 ISBN 978-92-1-139136-7 (complete set of two volumes) ISSN 1014-5753 Volumes I and II not to be sold separately FOREWORD The Recommendations on the Transport of Dangerous Goods are addressed to governments and to the international organizations concerned with safety in the transport of dangerous goods. The first version, prepared by the United Nations Economic and Social Council's Committee of Experts on the Transport of Dangerous Goods, was published in 1956 (ST/ECA/43-E/CN.2/170). In response to developments in technology and the changing needs of users, they have been regularly amended and updated at succeeding sessions of the Committee of Experts pursuant to Resolution 645 G (XXIII) of 26 April 1957 of the Economic and Social Council and subsequent resolutions.
    [Show full text]
  • Problématiques Environnementales Et Du Développement Durable
    Université Paris EST Ecole Doctorale Sciences, Ingénierie et Environnement THESE DE DOCTORAT Présentée par: SEYDINA IBRAHIMA KEBE Pour obtenir le grade de Docteur de l’Université Paris EST Spécialité : Chimie et Sciences des Matériaux Sujet de Thèse : Synthèse de matériaux monolithiques pour la séparation et la catalyse en phase liquide: Problématiques environnementales et du développement durable Soutenance le 9 décembre 2016 Devant la commission d’examen formée de : K. Faure : Chargée de recherche, CNRS Rapporteur T. Tran-Maignan : Maître de conférences Rapporteur F. Le Derf : Professeur Examinateur A. Elaissari : Directeur de recherche, CNRS Examinateur A. Bressy : Chargée de recherche, CNRS Membre invité M. Guerrouache : Ingénieur de recherche Membre invité B. Carbonnier : Professeur Directeur de thèse Thèse réalisée au sein de l’équipe Systèmes Polymères Complexes, ICMPE, CNRS, Thiais France Remerciements Je tiens à profiter de ce rapport pour exprimer mes plus grands et chaleureux remerciements envers tous ceux qui ont, en leur manière, contribué à la réussite de cette thèse Cette thèse a pu être réalisée grâce à l'accueil Madame Valérie LANGLOIS adjointe directrice de l’ICMPE, directrice du SPC professeur et chercheuse à l’Université Paris Est Créteil (UPEC). Je lui témoigne ma reconnaissance. Je n’aurais jamais commencé sans exprimer tout particulièrement mes plus grands remerciements et à témoigner toute ma reconnaissance à Benjamin CARBONNIER mon directeur de thèse, professeur des universités à l’UPEC pour l’expérience enrichissante qu’il m’a fait vivre. De simples mots, ne sauraient décrire ma satisfaction à son égard. Je tiens à remercier Mohamed GUERROUACHE, ingénieur, pour son temps consacré à me donner des explications et à me guider.
    [Show full text]
  • United States Patent Office Patented Apr
    3,505,222 United States Patent Office Patented Apr. 7, 1970 1. 2 3,505,222 product of a mercaptain with sulfur trioxide. Their metal LUBRICANT COMPOSITIONS salts are represented by the formula: Leonard M. Niebylski, Birmingham, Mich, assignor to O Ethyl Corporation, New York, N.Y., a corporation of Virginia (R-S-S-0--M No Drawing. Filed Mar. 29, 1967, Ser. No. 626,701 5 s (I) Int. C. C10m 5/14, 3/18, 7/36 wherein R is a hydrocarbon radical containing from 1 U.S. C. 252-17 2 Claims to about 30 carbon atoms, M is a metal, and n is the valence of metal M. For example, when M is the monova 0. lent sodium ion, n is 1. ABSTRACT OF THE DISCLOSURE The radical R can be an alkyl, cycloalkyl, aralkyl, The extreme pressure wear properties of base lubri alkaryl, or aryl radical. The radicals may contain other cants including water, hydrocarbons, polyesters, silicones, nonhydrocarbon substituents such as chloro, bromo, iodo, polyethers and halocarbons is enhanced by the addition fluoro, nitro, hydroxyl, nitrile, isocyanate, carboxyl, car of a synergistic mixture of a thiosulfate compound and 15 bonyl, and the like. a lead compound. The useful metals are all those capable of forming Bunte salts. Preferred metals are those previously listed as suitable for forming metal thiosulfates. Of these, the Background more preferred metals are sodium and lead, and lead is 20 the most preferred metal in the Bunte salts. This invention relates to improved lubricant composi Examples of useful Bunte salts include: tions.
    [Show full text]
  • University of California Riverside
    UNIVERSITY OF CALIFORNIA RIVERSIDE Natamycin, a New Postharvest Biofungicide: Toxicity to Major Decay Fungi, Efficacy, and Optimized Usage Strategies A Dissertation submitted in partial satisfaction of the requirements for the degree of Doctor of Philosophy in Plant Pathology by Daniel Sungen Chen September 2020 Dissertation Committee: Dr. James E. Adaskaveg, Chairperson Dr. Michael E. Stanghellini Dr. Alexander I. Putman Copyright by Daniel Sungen Chen 2020 The Dissertation of Daniel Sungen Chen is approved: Committee Chairperson University of California, Riverside AKNOWLEDGEMENTS Foremost, I thank my mentor Dr. James E. Adaskaveg for accepting me into his research program and teaching me the intricacies of the field of postharvest plant pathology and preparing me for a bright career ahead. His knowledge of the field is unmatched. A special thanks goes out to Dr. Helga Förster, whose expertise and attention to detail has helped me out tremendously in my research and writings. I thank my dissertation committee members, Dr. Michael Stanghellini and Dr. Alexander Putman, for their time spent reviewing my dissertation and their guidance during the pursuit of my doctoral degree. Special thanks also go out to my lab members Dr. Rodger Belisle, Dr. Wei Hao, Dr. Kevin Nguyen, and Nathan Riley for their companionship and much appreciated help with my projects. I would also like to thank my former laboratory members, Dr. Stacey Swanson and Dr. Morgan Thai for their guidance and help during the early years of my graduate program. Thanks go out to Dr. Lingling Hou, Dr. Yong Luo, and Doug Cary for their assistance with performing experimental packingline studies at the Kearney Agricultural Research and Extension Center.
    [Show full text]
  • Updates in Ocular Antifungal Pharmacotherapy: Formulation and Clinical Perspectives
    Current Fungal Infection Reports (2019) 13:45–58 https://doi.org/10.1007/s12281-019-00338-6 PHARMACOLOGY AND PHARMACODYNAMICS OF ANTIFUNGAL AGENTS (N BEYDA, SECTION EDITOR) Updates in Ocular Antifungal Pharmacotherapy: Formulation and Clinical Perspectives Ruchi Thakkar1,2 & Akash Patil1,2 & Tabish Mehraj1,2 & Narendar Dudhipala1,2 & Soumyajit Majumdar1,2 Published online: 2 May 2019 # Springer Science+Business Media, LLC, part of Springer Nature 2019 Abstract Purpose of Review In this review, a compilation on the current antifungal pharmacotherapy is discussed, with emphases on the updates in the formulation and clinical approaches of the routinely used antifungal drugs in ocular therapy. Recent Findings Natamycin (Natacyn® eye drops) remains the only approved medication in the management of ocular fungal infections. This monotherapy shows therapeutic outcomes in superficial ocular fungal infections, but in case of deep-seated mycoses or endophthalmitis, successful therapeutic outcomes are infrequent, as a result of which alternative therapies are sought. In such cases, amphotericin B, azoles, and echinocandins are used off-label, either in combination with natamycin or with each other (frequently) or as standalone monotherapies, and have provided effective therapeutic outcomes. Summary In recent times, amphotericin B, azoles, and echinocandins have come to occupy an important niche in ocular antifungal pharmacotherapy, along with natamycin (still the preferred choice in most clinical cases), in the management of ocular fungal infections.
    [Show full text]
  • Magnetic Graphene Oxide Modified by Chloride Imidazole Ionic Liquid For
    RSC Advances View Article Online PAPER View Journal | View Issue Magnetic graphene oxide modified by chloride imidazole ionic liquid for the high-efficiency Cite this: RSC Adv.,2017,7,9079 adsorption of anionic dyes† Huan Wangab and Yinmao Wei*a Magnetic graphene oxide modified with 1-amine-3-methyl imidazole chloride ionic liquid (LI-MGO) was prepared through chemical co-precipitation and modified using 1-amine-3-imidazolium chloride ionic liquid. The as-prepared LI-MGO was characterized using X-ray diffraction (XRD), transmission electron microscopy (TEM) and Fourier transform infrared spectrometry (FT-IR). The adsorption properties were evaluated through adsorption experiments with two kinds of anionic dyes, orange IV (OIV) and glenn black R (GR) and two kinds of cationic dyes, acridine orange (AO) and crystal violet (CV). The results indicated that the adsorption data fitted the Langmuir isotherm and followed pseudo-second-order kinetics. The maximum adsorption capacities for GR, OIV, AO and CV were 588.24, 57.37, 132.80 and Received 29th November 2016 À1 Creative Commons Attribution 3.0 Unported Licence. 69.44 mg g at 298 K, respectively. LI-MGO has better selective adsorption for anionic dyes than Accepted 17th January 2017 magnetic graphene oxide (MGO) due to electrostatic interactions. Moreover, the LI-MGO adsorbent can DOI: 10.1039/c6ra27530c be magnetic separated and is easy to prepare. It demonstrated that LI-MGO would have great potential rsc.li/rsc-advances as an efficient environmentally friendly adsorbent for the removal of anionic
    [Show full text]
  • Synthesis of Photoreactive Imidazole Derivatives and Thermal Curing Reaction of Epoxy Resins Catalyzed by Photo-Generated Imidazole
    Polymer Journal, Vol. 29, No. 5, pp 450-456 (1997) Synthesis of Photoreactive Imidazole Derivatives and Thermal Curing Reaction of Epoxy Resins Catalyzed by Photo-Generated Imidazole Tadatomi NrsHIKUBO,t Atsushi KAMEYAMA, and Yoshiyasu TOYA Department of' Applied Chemistry, Faculty of Engineering, Kanagawa University, Rokkakubashi, Kanagawa-ku, Yokohama, 221 Japan (Received November 6, 1996) ABSTRACT: Photoreactive blocked imidazoles such as N-(2-nitrobenzyloxycarbonyl)imidazole (2-NBCI), N-(3-nitro­ benzyloxycarbonyl)imidazole (3-NBCI), N-( 4-nitrobenzyloxycarbonyl)imidazole (4- NBCI), N-( 4-chloro-2-nitro benzyloxy­ carbonyl )imidazole (CNBCI), N-(5-methyl-2-nitrobenzyloxycarbonyl)imidazole (MNBCI), and N-(4,5-dimethoxy-2-ni­ trobenzyloxycarbonyl)imidazole (DNBCI) were synthesized in good yields by reactions of N,N'-carbonyldiimidazole (CDI) with corresponding benzyl alcohols. The prepared 2-NBCI decomposed smoothly to produce imidazole by UV-irradiation in tetrahydrofuran (THF) solution or poly(methyl methacrylate) (PMMA) film. Rates of photolysis of DNBCI, MNBCI and CNBCI were higher than that of 2-NBCI in PMMA film, although the rates of 3-NBCI and 4-NBCI were slower than that of 2-NBCI in PMMA film under the same conditions. Thermal curing reactions of epoxy resins and poly(glycidyl methacrylate-co-methyl methacrylate) [P(GMA55-MMA45)] using photo-generated imidazole were examined at I00-160°C. The ring opening reaction of epoxide groups, confirmed by IR spectra, in epoxy resins and P(GMA55-MMA45) proceeded smoothly by catalysis of the photo-generated imidazole. KEY WORDS Synthesis of Blocked Imidazole /Photo-Generation/ Imidazole / Thermal Curing Reaction / Epoxy Resin/ Poly(glycidyl methacrylate-co-methyl methac!ylate) / Epoxy resins are typical thermo-setting resins, and Tsunooka et al.
    [Show full text]
  • Arylsulfonylmethyl Isocyanides: a Novel Paradigm in Organic Synthesis
    RSC Advances This is an Accepted Manuscript, which has been through the Royal Society of Chemistry peer review process and has been accepted for publication. Accepted Manuscripts are published online shortly after acceptance, before technical editing, formatting and proof reading. Using this free service, authors can make their results available to the community, in citable form, before we publish the edited article. This Accepted Manuscript will be replaced by the edited, formatted and paginated article as soon as this is available. You can find more information about Accepted Manuscripts in the Information for Authors. Please note that technical editing may introduce minor changes to the text and/or graphics, which may alter content. The journal’s standard Terms & Conditions and the Ethical guidelines still apply. In no event shall the Royal Society of Chemistry be held responsible for any errors or omissions in this Accepted Manuscript or any consequences arising from the use of any information it contains. www.rsc.org/advances Page 1 of 22 RSC Advances Arylsulfonylmethyl isocyanides: α-acidity in the structure of isocyanides Tanpreet Kaur, Preeti Wadhwa and Anuj Sharma* *Department of Chemistry, Indian Institute of Technology, Roorkee-247667, India (Phone: +91-1332-284751; e-mail: [email protected] ) Abstract: p-Tosylmethyl isocyanide (TosMIC), an α-acidic isocyanide has emerged as a privileged reagent to access biologically relevant scaffolds. The present review highlights the significant advancements of TosMIC in the construction of fused heterocycles viz. pyrroles, benzimidazoles, imidazopyridines, quinolones, quinolines and some natural products like (-)-Ushikulide A, Variolin B, Porphobilinogen and mansouramycin B. The review article encompasses literature from the period starting from 2010 onwards and covers novel synthetic methodologies involving TosMIC.
    [Show full text]
  • No 1223/2009 of the EUROPEAN PARLIAMENT and of the COUNCIL of 30 November 2009 on Cosmetic Products (Recast) (Text with EEA Relevance) (OJ L 342, 22.12.2009, P
    02009R1223 — EN — 03.12.2020 — 025.001 — 1 This text is meant purely as a documentation tool and has no legal effect. The Union's institutions do not assume any liability for its contents. The authentic versions of the relevant acts, including their preambles, are those published in the Official Journal of the European Union and available in EUR-Lex. Those official texts are directly accessible through the links embedded in this document ►B REGULATION (EC) No 1223/2009 OF THE EUROPEAN PARLIAMENT AND OF THE COUNCIL of 30 November 2009 on cosmetic products (recast) (Text with EEA relevance) (OJ L 342, 22.12.2009, p. 59) Amended by: Official Journal No page date ►M1 Commission Regulation (EU) No 344/2013 of 4 April 2013 L 114 1 25.4.2013 ►M2 Commission Regulation (EU) No 483/2013 of 24 May 2013 L 139 8 25.5.2013 ►M3 Commission Regulation (EU) No 658/2013 of 10 July 2013 L 190 38 11.7.2013 ►M4 Commission Regulation (EU) No 1197/2013 of 25 November 2013 L 315 34 26.11.2013 ►M5 Commission Regulation (EU) No 358/2014 of 9 April 2014 L 107 5 10.4.2014 ►M6 Commission Regulation (EU) No 866/2014 of 8 August 2014 L 238 3 9.8.2014 ►M7 Commission Regulation (EU) No 1003/2014 of 18 September 2014 L 282 1 26.9.2014 ►M8 Commission Regulation (EU) No 1004/2014 of 18 September 2014 L 282 5 26.9.2014 ►M9 Commission Regulation (EU) 2015/1190 of 20 July 2015 L 193 115 21.7.2015 ►M10 Commission Regulation (EU) 2015/1298 of 28 July 2015 L 199 22 29.7.2015 ►M11 Commission Regulation (EU) 2016/314 of 4 March 2016 L 60 59 5.3.2016 ►M12 Commission Regulation (EU)
    [Show full text]
  • Recent Advances in the Synthesis of Oxazole-Based Molecules Via Van Leusen Oxazole Synthesis
    molecules Review Recent Advances in the Synthesis of Oxazole-Based Molecules via van Leusen Oxazole Synthesis Xunan Zheng 1,2, Wei Liu 3,* and Dawei Zhang 1,* 1 College of Chemistry, Jilin University, Changchun 130012, China; [email protected] 2 College of Plant Science, Jilin University, Changchun 130062, China 3 Department of Pesticide Science, Plant Protection College, Shenyang Agricultural University, Shenyang 110866, China * Correspondence: [email protected] (W.L.); [email protected] (D.Z.); Tel.: +86-188-1775-2588 (W.L.); +86-431-8783-6471 (D.Z.) Academic Editors: Anna Carbone and Fabio Bertozzi Received: 2 March 2020; Accepted: 23 March 2020; Published: 31 March 2020 Abstract: Oxazole compounds, including one nitrogen atom and one oxygen atom in a five-membered heterocyclic ring, are present in various biological activities. Due to binding with a widespread spectrum of receptors and enzymes easily in biological systems through various non-covalent interactions, oxazole-based molecules are becoming a kind of significant heterocyclic nucleus, which have received attention from researchers globally, leading them to synthesize diverse oxazole derivatives. The van Leusen reaction, based on tosylmethylisocyanides (TosMICs), is one of the most appropriate strategies to prepare oxazole-based medicinal compounds. In this review, we summarize the recent advances of the synthesis of oxazole-containing molecules utilizing the van Leusen oxazole synthesis from 1972, aiming to look for potential oxazole-based medicinal compounds, which are valuable information for drug discovery and synthesis. Keywords: van Leusen; TosMICs; oxazole; synthesis 1. Introduction The oxazole ring, with one nitrogen atom and one oxygen atom, which are widely displayed in natural products and synthetic molecules, is known as a prime skeleton for drug discovery.
    [Show full text]
  • Total Synthesis of Caribenol a and Caribenol B
    Literature Report 2 Total Synthesis of Caribenol A and Caribenol B Reporter : Xiao-Yong Zhai Checker : Shubo Hu Date : 2017-04-24 Hao, H.-D.; Trauner, D. J. Am. Chem. Soc. 2017, 139, 4117. CV of Dirk Trauner Education: 1986–1991 B.S., University of Vienna 1992–1995 M.S., Free University of Berlin 1996–1997 Ph.D., University of Vienna 1998–2000 Postdoc., Memorial Sloan Kettering Cancer Center 2001–2008 Associate Professor, University of California, Berkeley 2009-2017 Professor, University of Munich and New York University Dirk Trauner Research: chemical synthesis, natural product chemistry, neuroscience, cell biology and photopharmacology. 2 Contents 1 Introduction 2 Total Synthesis of Caribenol A 3 Total Synthesis of Caribenol B 4 Summary 3 Introduction Me H H B C A HO Me Me O O Caribenol A Pseudopterogorgia Isolated from the Pseudopterogorgia elisabethae in 2007; Exhibiting biological activity against Mycobacterium tuberculosis H37Rv and plasmodium; A caged structure and tricarbocyclic ring system with six stereocenters. Wei, X.; Rodríguez, I. I.; Rodríguez, A. D.; Barnes, C. L. J. Org. Chem. 2007, 72, 7386. 4 Introduction Natural products isolated from Pseudopterogorgia elisabethae Me H Me H Me H H Me H O Me O O H Me Me O H O O O OH O Aberrarone Elisabethin A Amphilectolide Me Me Me H H H H OH HO HO Me Me Me Me HO Me O OH O Me O O O Caribenol B Caribenol A Sandresolide B Wei, X.; Rodríguez, I. I.; Rodríguez, A. D.; Barnes, C. L. J. Org. Chem. 2007, 72, 7386. 5 Retrosynthetic analysis of Caribenol A O O CO Me O O O 2 Me Me Me Me Me Me TBSO Me Me A C A OH C A H C B B B H H H H H Me Me Me Caribenol A (1) 2 3 O H Me CO2Me Me CO2Me Me + + Me O I TBSO CO Me Me Me 2 4 7 6 5 Liu, L-Z.; Han, J-C.; Yue, G-Z.; Li, C-C.; Yang, Z.
    [Show full text]
  • List of Lists
    United States Office of Solid Waste EPA 550-B-10-001 Environmental Protection and Emergency Response May 2010 Agency www.epa.gov/emergencies LIST OF LISTS Consolidated List of Chemicals Subject to the Emergency Planning and Community Right- To-Know Act (EPCRA), Comprehensive Environmental Response, Compensation and Liability Act (CERCLA) and Section 112(r) of the Clean Air Act • EPCRA Section 302 Extremely Hazardous Substances • CERCLA Hazardous Substances • EPCRA Section 313 Toxic Chemicals • CAA 112(r) Regulated Chemicals For Accidental Release Prevention Office of Emergency Management This page intentionally left blank. TABLE OF CONTENTS Page Introduction................................................................................................................................................ i List of Lists – Conslidated List of Chemicals (by CAS #) Subject to the Emergency Planning and Community Right-to-Know Act (EPCRA), Comprehensive Environmental Response, Compensation and Liability Act (CERCLA) and Section 112(r) of the Clean Air Act ................................................. 1 Appendix A: Alphabetical Listing of Consolidated List ..................................................................... A-1 Appendix B: Radionuclides Listed Under CERCLA .......................................................................... B-1 Appendix C: RCRA Waste Streams and Unlisted Hazardous Wastes................................................ C-1 This page intentionally left blank. LIST OF LISTS Consolidated List of Chemicals
    [Show full text]