Stereoselective Asymmetric Syntheses of Molecules with a 4,5-Dihydro-1H-[1,2,4]-Triazoline Core Possessing an Acetylated Carbohydrate Appendage: Crystal Structure, Spectroscopy, and Pharmacology-Reference-Cited by-同舟云学术

Stereoselective Asymmetric Syntheses of Molecules with a 4,5-Dihydro-1H-[1,2,4]-Triazoline Core Possessing an Acetylated Carbohydrate Appendage: Crystal Structure, Spectroscopy, and Pharmacology

Published:2024-06-14 Issue:12 Volume:29 Page:2839
ISSN:1420-3049
Container-title:Molecules
language:en
Short-container-title:Molecules

Author:

Al Maqbali Anwaar S.¹,Al Rasbi Nawal K.¹^ORCID,Zoghaib Wajdi M.¹,Sivakumar Nallusamy²^ORCID,Robertson Craig C.³^ORCID,Shongwe Musa S.¹^ORCID,Grzegorzek Norbert⁴^ORCID,Abdel-Jalil Raid J.¹^ORCID

Affiliation:

1. Department of Chemistry, College of Science, Sultan Qaboos University, Al-Khod 123, Muscat P.O. Box 36, Oman

2. Department of Biology, College of Science, Sultan Qaboos University, Al-Khod 123, Muscat P.O. Box 36, Oman

3. Department of Chemistry, University of Sheffield, Sheffield S3 7HF, UK

4. Institute of Organic Chemistry, University of Tübingen, Auf Der Morgenstelle 18, A-Bau, 72076 Tübingen, Germany

Abstract

A new series of chiral 4,5-dihydro-1H-[1,2,4]-triazoline molecules, featuring a β-ᴅ-glucopyranoside appendage, were synthesized via a 1,3-dipolar cycloaddition reaction between various hydrazonyl chlorides and carbohydrate Schiff bases. The isolated enantiopure triazolines (8a–j) were identified through high-resolution mass spectrometry (HRMS) and vibrational spectroscopy. Subsequently, their solution structures were elucidated through NMR spectroscopic techniques. Single-crystal X-ray analysis of derivative 8b provided definitive evidence for the 3-D structure of this compound and revealed important intermolecular forces in the crystal lattice. Moreover, it confirmed the (S)-configuration at the newly generated stereo-center. Selected target compounds were investigated for anti-tumor activity in 60 cancer cell lines, with derivative 8c showing the highest potency, particularly against leukemia. Additionally, substituent-dependent anti-fungal and anti-bacterial behavior was observed.

Funder

Sultan Qaboos University

Publisher

MDPI AG

Link

https://www.mdpi.com/1420-3049/29/12/2839/pdf

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