PDF(Pubmed)
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.
摘要：
一系列新的手性4,5-二氢-1H-[1,2,4]-三唑啉分子,具有β-β-吡喃葡萄糖苷附属物，通过各种肼酰氯和碳水化合物席夫碱之间的1,3-偶极环加成反应合成。通过高分辨率质谱（HRMS）和振动光谱法鉴定了分离的对映体纯的三唑啉（8a-j）。随后，通过NMR光谱技术阐明了它们的溶液结构。衍生物8b的单晶X射线分析为该化合物的3-D结构提供了明确的证据，并揭示了晶格中重要的分子间力。此外，它确认了新生成的立体声中心的（S）配置。研究了选定的目标化合物在60种癌细胞系中的抗肿瘤活性，衍生物8c显示出最高的效力，特别是针对白血病。此外,观察到取代基依赖性抗真菌和抗菌行为。
