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The Studies on Momordica Charantia Fruits and the Synthesis of Pyrazolyl The studies on Momordica charantia fruits and the synthesis of pyrazolyl substituted benzylidene indanone derivatives as dengue virus type-2 NS2B/NS3 protease inhibitor Nadirah Zawani Mohd Nesfu To cite this version: Nadirah Zawani Mohd Nesfu. The studies on Momordica charantia fruits and the synthesis of pyrazolyl substituted benzylidene indanone derivatives as dengue virus type-2 NS2B/NS3 protease inhibitor. Organic chemistry. Université de Lorraine; Universiti Sains Malaysia (Malaisie), 2020. English. NNT : 2020LORR0092. tel-02969953 HAL Id: tel-02969953 https://hal.univ-lorraine.fr/tel-02969953 Submitted on 17 Oct 2020 HAL is a multi-disciplinary open access L’archive ouverte pluridisciplinaire HAL, est archive for the deposit and dissemination of sci- destinée au dépôt et à la diffusion de documents entific research documents, whether they are pub- scientifiques de niveau recherche, publiés ou non, lished or not. The documents may come from émanant des établissements d’enseignement et de teaching and research institutions in France or recherche français ou étrangers, des laboratoires abroad, or from public or private research centers. publics ou privés. AVERTISSEMENT Ce document est le fruit d'un long travail approuvé par le jury de soutenance et mis à disposition de l'ensemble de la communauté universitaire élargie. Il est soumis à la propriété intellectuelle de l'auteur. Ceci implique une obligation de citation et de référencement lors de l’utilisation de ce document. D'autre part, toute contrefaçon, plagiat, reproduction illicite encourt une poursuite pénale. Contact : [email protected] LIENS Code de la Propriété Intellectuelle. articles L 122. 4 Code de la Propriété Intellectuelle. articles L 335.2- L 335.10 http://www.cfcopies.com/V2/leg/leg_droi.php http://www.culture.gouv.fr/culture/infos-pratiques/droits/protection.htm Ecole Doctorale C2MP (Chimie - Mécanique - Matériaux- Physique) Thèse en cotutelle entre l’Université de Lorraine et l’Universiti Sains malaysia Présentée et soutenue publiquement pour l’obtention du titre de DOCTEUR DE l’UNIVERSITE DE LORRAINE en Chimie par Nadirah Zawani BINTI MOHD NESFU Les études sur les fruits de Momordica charantia et la synthèse de dérivés de benzylidène indanone pyrazolyl substitués comme inhibiteurs de la protéase NS2B/NS3 du virus de la dengue de type 2 Le 01 Septembre 2020 Président du Jury: Professeur, Anne-Claire OFFER Université de Bourgogne Franche-Comté, France Rapporteurs: Ahmad Sazali HAMZAH Professeur, Universiti Teknologi MARA, Selangor, Malaysia Examinateurs: Melati KHAIRUDDEAN Assistant Professeur, Universiti Sains Malaysia, Penang, Malaysia Vikneswaran MURUGAIYAH Maitre, Universiti Sains Malaysia, Penang, Malaysia Membres invités: Dominique LAURAIN-MATTAR Professeur, Université de Lorraine, France Directeur de these Hasnah OSMAN Professeur, Universiti Sains Malaysia, Penang, Malaysia, Directeur de these Nicolas BROSSE Professeur, Université de Lorraine, France Co-directeur de these Ezatul E. KAMARULZAMAN Maitre, Universiti Sains Malaysia, Penang, Malaysia. Co-directeur de these Laboratoire L2CM, UMR 7053, Faculté des Sciences et Technologies, Boulevard des Aiguillettes, BP 70239,54506 Vandoeuvre-lès-Nancy,France School of Chemical Sciences, Universiti Sains Malaysia, 11800 Gelugor Penang, Malaysia THE STUDIES ON MOMORDICA CHARANTIA FRUITS AND THE SYNTHESIS OF PYRAZOLYL SUBSTITUTED BENZYLIDENE INDANONE DERIVATIVES AS DENGUE VIRUS TYPE-2 NS2B/NS3 PROTEASE INHIBITOR NADIRAH ZAWANI BINTI MOHD NESFU UNIVERSITI SAINS MALAYSIA 2020 THE STUDIES ON MOMORDICA CHARANTIA FRUITS AND THE SYNTHESIS OF PYRAZOLYL SUBSTITUTED BENZYLIDENE INDANONE DERIVATIVES AS DENGUE VIRUS TYPE-2 NS2B/NS3 PROTEASE INHIBITOR by NADIRAH ZAWANI BINTI MOHD NESFU Thesis submitted in fulfillment of the requirements for the degree of Doctor of Philosophy October 2020 DEDICATION Alhamdulillah. I would like to dedicate my thesis to: IBU, my mother, my backbone, my strength. ABAH, you’re gone but your words of wisdom are not forgotten. ARIFFUDIN, a shoulder to cry on, a good listener, and my supporter. KAK DIAH & IEAH, sisters, best friends, my everything. Thank you for being by my side thru thick and thin. I am so blessed to have all of you. May Allah bless all of you. ACKNOWLEDGEMENT All praise, glory and thanks give to Allah s.w.t for His amazing grace and generous that helps me throughout the whole process of completing this research I would like to take this opportunity to express my gratitude to my beloved supervisor, Prof. Dato’ Dr. Hasnah Osman, for her guidance, knowledge, support and advice along the way of finishing this research. I want to thank my supervisor from the University of Lorraine, France, Prof. Dr. Dominique Laurain-Mattar and Prof. Dr. Nicolas Brosse for their mentorship, guidance, trust, and patience during my work in their lab (CNRS and LERMAB), in administrative work in France as well as in writing my report and thesis. The experiences obtained during my stay in France will not be forgotten. I wish to take this chance to thank Prof. Dr. Afidah and Dr. Hazwan for their guidance and help in path a way for my dual PhD program and administrative works. Besides, I would like to thank all the School of Chemical Sciences lecturers and staff, the Institute of Postgraduate Studies (IPS) staff, the staff of Malaysian Institute of Pharmaceuticals and Nutraceuticals (IPharm), as well as University of Lorraine, France staff for their hospitality, supports, assistances and helps. Special thanks to the France Embassy in Malaysia, Minister of Foreign Affair France, Campus France and Ministry of Education Malaysia under MyPhD program for the scholarship and financial support. Last but not the least, I would like to thank my parent (Abah & Mak) and family members (especially; Kak Diah, Ieah & Ariffudin) for their patience, encouragement, understanding and care during the hardship and the difficult times. Thank you so much and I am so grateful for your support and help. ii TABLE OF CONTENTS ACKNOWLEDGEMENT ii TABLE OF CONTENTS iii LIST OF TABLES x LIST OF FIGURES xi LIST OF SCHEMES xiv LIST OF SYMBOLS xv LIST OF ABBREVIATIONS xvi ABSTRAK xviii ABSTRACT xx RÉSUMÉ xxii CHAPTER 1 INTRODUCTION 1 1.1 Background of the study 1 1.2 Problem statement 2 1.3 Rationale of the study 5 1.4 Hypothesis of the study 6 1.5 Objectives of the study 7 1.6 Scope of the study 8 1.7 Study flowchart 10 CHAPTER 2 LITERATURE REVIEW 11 2.1 M. charantia overview 11 2.1.1 The phytochemical studies on of M. charantia fruit 12 2.1.2 The phytochemical studies of M. charantia seeds 16 2.2 The extraction method of M. charantia 18 2.2.1 The fruits flesh extraction via maceration method 18 2.2.2 The M. charantia seed oil extraction method 19 iii 2.2.2(a) The enzyme-assisted aqueous extraction (AEE) oil extraction method 19 2.3 The indanone with gallic acid moieties derivatives 20 2.3.1 Gallic acid 20 2.3.2 The indanone 21 2.3.3 The synthesis of indanone-based derivatives and its pharmacological studies 22 2.4 Dengue virus 28 2.4.1 Dengue virus infection in Malaysia 28 2.4.2 Dengue virus treatment 30 2.4.3 The anti-dengue screening using DENV-2 NS2B/NS3 protease enzyme 30 2.4.4 The compounds with anti-dengue properties 34 CHAPTER 3 RESEARCH METHODOLOGY 37 3.1 Chemical and materials 37 3.2 Characterization methods 37 3.2.1 Melting point 37 3.2.2 Fourier-transform infrared (FTIR) spectroscopy 37 3.2.3 Nuclear magnetic resonance (NMR) spectroscopy 38 3.2.4 Gas chromatography (GC) analysis 38 3.2.5 Gas chromatography-mass spectrometry (GC-MS) 39 3.2.6 Liquid chromatography-mass spectrometry (LC-MS) 39 3.3 The studies of M. charantia fruits flesh and seed 39 3.3.1 Sample preparation 41 3.3.1(a) PART 1: Aqueous enzyme extraction (AEE) of M. charantia seed oil 41 3.3.1(a)(i) The analysis of M. charantia seed oil 42 3.3.1(a)(ii) The soxhlet extraction of the seed residue 43 iv 3.3.1(a)(iii) Determinations of lignin, soluble sugars, and uronic acid of EFM 43 3.3.1(a)(iv) Determination of soluble sugar and uronic acid contents of EFM 44 3.3.1(a)(v) Hemicellulose extraction of EFM 45 3.3.1(a)(vi) The SEC analysis of hemicellulose 46 3.3.1(b) PART 2: Preparation of M. charantia fruit flesh extract 47 3.3.2 Anti-dengue testing of M. charantia fruits flesh extract 47 3.4 The synthesis of pyrazolyl substituted benzylidene indanone derivatives 49 3.4.1 The synthesis of ethyl 3,4,5-trimethoxybenzoate, 85 and 4,5-trimethoxybenzohydrazide, 86 50 3.4.1(a) Ethyl 3,4,5-trimethoxybenzoate, 85 51 3.4.1(b) 3,4,5-trimethoxybenzohydrazide, 86 52 3.4.2 The synthesis of benzylidene indanone derivatives, 89a-t 52 3.4.2(a) (E)-2-benzylidene-1-indanone, 89a 53 3.4.2(b) (E)-5’‐methoxybenzylidene-1-indanone, 89b 54 3.4.2(c) (E)-5’-methylbenzylidine-1-indanone, 89c 55 3.4.2(d) (E)-5’-chlorolbenzylidine-1-indanone, 89d 55 3.4.2(e) (E)-2-(5’-isopropylbenzylidene)-1-indanone, 89e 56 3.4.2(f) (E)-2-(5’dimethylamino benzylidene)-1-indanone, 89f 57 3.4.2(g) (E)-2-[5’-(4”-morpholinobenzylidene)]-1- indanone, 89g 57 3.4.2(h) (E)-2-(5’-piperidinylbenzylidene)-1-indanone, 89h 58 3.4.2(i) (E)-2-(3’,5’-dimethoxybenzylidene)-1-indanone, 89i 59 3.4.2(j) (E)-2-(4’-nitro-5’methoxybenzylidene)-1- indanone, 89j 59 3.4.2(k) (E)-2-benzylidine-5,6-dimethoxy-1-indanone, 89k 60 v 3.4.2(l) (E)-(5’‐methoxybenzylidene)-5,6-dimethoxy- 1indanone, 89l 61 3.4.2(m) (E)-(5’-methylbenzylidine)‐6,7- dimethoxy‐1- indanone, 89m 61 3.4.2(n) (E)-(5’-chlorobenzylidine)‐6,7-dimethoxy‐1- indanone, 89n 62 3.4.2(o) (E)-2-(5’-isopropylbenzylidene)-5,6-dimethoxy-1- indanone, 89o 63
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