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Crystallography, Molecular Modeling, and COX-2 Inhibition Studies on Indolizine Derivatives.

التفاصيل البيبلوغرافية
العنوان: Crystallography, Molecular Modeling, and COX-2 Inhibition Studies on Indolizine Derivatives.
المؤلفون: Venugopala KN; Department of Pharmaceutical Sciences, College of Clinical Pharmacy, King Faisal University, Al-Ahsa 31982, Saudi Arabia.; Department of Biotechnology and Food Technology, Durban University of Technology, Durban 4001, South Africa., Chandrashekharappa S; Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER-R) Raebareli, Lucknow UP 226002, India.; Institute for Stem Cell Science and Regenerative Medicine, NCBS, TIFR, GKVK, Bellary Road, Bangalore 560065, India., Tratrat C; Department of Pharmaceutical Sciences, College of Clinical Pharmacy, King Faisal University, Al-Ahsa 31982, Saudi Arabia., Deb PK; Faculty of Pharmacy, Philadelphia University, Amman 19392, Jordan., Nagdeve RD; Department of Chemistry, Visvesvaraya National Institute of Technology, Nagpur 440010, Maharashtra, India., Nayak SK; Department of Chemistry, Visvesvaraya National Institute of Technology, Nagpur 440010, Maharashtra, India., Morsy MA; Department of Pharmaceutical Sciences, College of Clinical Pharmacy, King Faisal University, Al-Ahsa 31982, Saudi Arabia.; Department of Pharmacology, Faculty of Medicine, Minia University, El-Minia 61511, Egypt., Borah P; Pratiksha Institute of Pharmaceutical Sciences, Chandrapur Road, Panikhaiti, Guwahati 781026, Assam, India., Mahomoodally FM; Department of Health Sciences, Faculty of Medicine and Health Sciences, University of Mauritius, Réduit 80835, Mauritius., Mailavaram RP; Department of Pharmaceutical Chemistry, Shri Vishnu College of Pharmacy, Vishnupur, Bhimavaram 534202, India., Attimarad M; Department of Pharmaceutical Sciences, College of Clinical Pharmacy, King Faisal University, Al-Ahsa 31982, Saudi Arabia., Aldhubiab BE; Department of Pharmaceutical Sciences, College of Clinical Pharmacy, King Faisal University, Al-Ahsa 31982, Saudi Arabia., Sreeharsha N; Department of Pharmaceutical Sciences, College of Clinical Pharmacy, King Faisal University, Al-Ahsa 31982, Saudi Arabia.; Department of Pharmaceutics, Vidya Siri College of Pharmacy, Off Sarjapura Road, Bangalore 560035, India., Nair AB; Department of Pharmaceutical Sciences, College of Clinical Pharmacy, King Faisal University, Al-Ahsa 31982, Saudi Arabia., Alwassil OI; Department of Pharmaceutical Sciences, College of Pharmacy, King Saud bin Abdulaziz University for Health Sciences, Riyadh 11481, Saudi Arabia., Haroun M; Department of Pharmaceutical Sciences, College of Clinical Pharmacy, King Faisal University, Al-Ahsa 31982, Saudi Arabia., Mohanlall V; Department of Biotechnology and Food Technology, Durban University of Technology, Durban 4001, South Africa., Shinu P; Department of Biomedical Sciences, College of Clinical Pharmacy, King Faisal University, Al-Ahsa 31982, Saudi Arabia., Venugopala R; Department of Public Health Medicine, Howard College Campus, University of KwaZulu-Natal, Durban 4001, South Africa., Kandeel M; Department of Biomedical Sciences, College of Veterinary Medicine, King Faisal University, Al-Ahsa 31982, Saudi Arabia.; Department of Pharmacology, Faculty of Veterinary Medicine, Kafrelsheikh University, Kafrelsheikh 33516, Egypt., Nandeshwarappa BP; Department of Studies in Chemistry, Shivagangotri, Davangere University, Davangere, Karnataka 577007, India., Ibrahim YF; Department of Pharmacology, Faculty of Medicine, Minia University, El-Minia 61511, Egypt.
المصدر: Molecules (Basel, Switzerland) [Molecules] 2021 Jun 10; Vol. 26 (12). Date of Electronic Publication: 2021 Jun 10.
نوع المنشور: Journal Article
اللغة: English
بيانات الدورية: Publisher: MDPI Country of Publication: Switzerland NLM ID: 100964009 Publication Model: Electronic Cited Medium: Internet ISSN: 1420-3049 (Electronic) Linking ISSN: 14203049 NLM ISO Abbreviation: Molecules Subsets: MEDLINE
أسماء مطبوعة: Original Publication: Basel, Switzerland : MDPI, c1995-
مواضيع طبية MeSH: Cyclooxygenase 2 Inhibitors/*chemistry , Indolizines/*chemistry, Anti-Inflammatory Agents/chemistry ; Crystallography, X-Ray/methods ; Cyclooxygenase 2/metabolism ; Humans ; Hydrophobic and Hydrophilic Interactions ; Indomethacin/chemistry ; Structure-Activity Relationship
مستخلص: The cyclooxygenase-2 (COX-2) enzyme is an important target for drug discovery and development of novel anti-inflammatory agents. Selective COX-2 inhibitors have the advantage of reduced side-effects, which result from COX-1 inhibition that is usually observed with nonselective COX inhibitors. In this study, the design and synthesis of a new series of 7-methoxy indolizines as bioisostere indomethacin analogues ( 5a - e ) were carried out and evaluated for COX-2 enzyme inhibition. All the compounds showed activity in micromolar ranges, and the compound diethyl 3-(4-cyanobenzoyl)-7-methoxyindolizine-1,2-dicarboxylate ( 5a ) emerged as a promising COX-2 inhibitor with an IC 50 of 5.84 µM, as compared to indomethacin (IC 50 = 6.84 µM). The molecular modeling study of indolizines indicated that hydrophobic interactions were the major contribution to COX-2 inhibition. The title compound diethyl 3-(4-bromobenzoyl)-7-methoxyindolizine-1,2-dicarboxylate ( 5c ) was subjected for single-crystal X-ray studies, Hirshfeld surface analysis, and energy framework calculations. The X-ray diffraction analysis showed that the molecule ( 5c ) crystallizes in the monoclinic crystal system with space group P 2 1 /n with a = 12.0497(6)Å, b = 17.8324(10)Å, c = 19.6052(11)Å, α = 90.000°, β = 100.372(1)°, γ = 90.000°, and V = 4143.8(4)Å 3 . In addition, with the help of Crystal Explorer software program using the B3LYP/6-31G(d, p) basis set, the theoretical calculation of the interaction and graphical representation of energy value was measured in the form of the energy framework in terms of coulombic, dispersion, and total energy.
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معلومات مُعتمدة: 186333 Deanship of Scientific Research, King Faisal University
فهرسة مساهمة: Keywords: COX-2 inhibition; Hirshfeld surface analysis; crystal structure; energy framework; indolizine derivatives; molecular modeling
المشرفين على المادة: 0 (Anti-Inflammatory Agents)
0 (Cyclooxygenase 2 Inhibitors)
0 (Indolizines)
274-40-8 (indolizine)
EC 1.14.99.1 (Cyclooxygenase 2)
XXE1CET956 (Indomethacin)
تواريخ الأحداث: Date Created: 20210702 Date Completed: 20210713 Latest Revision: 20210713
رمز التحديث: 20240628
مُعرف محوري في PubMed: PMC8230391
DOI: 10.3390/molecules26123550
PMID: 34200764
قاعدة البيانات: MEDLINE
الوصف
تدمد:1420-3049
DOI:10.3390/molecules26123550