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可控制的1,3-双功能化2-甘具有高区域选择性和立体选择性,由H键催化剂启用

Jiangtao Li^1,2, Zhengyan Fu^1,3, Zeen Qiao^1,2

¹Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, People's Republic of China.

|April 1, 2024

概括

研究人员开发了碳水化合物的C3功能化的新方法,为药物发现创造了非天然的糖类. 这些立体选择性反应产生了各种各样的碳水化合物衍生物,具有潜在的抗癌活性.

科学领域:

碳水化合物化学碳水化合物化学
有机合成有机合成
药用化学医学化学

背景情况:

选择性碳水化合物修饰对于开发新型非自然类型的药物发现至关重要.
虽然C1和C1,C2功能已经确立,但碳水化合物的C3或C1,C3功能仍然具有挑战性.
开发有效的C3功能化方法对于扩大基于碳水化合物的药物发现范围至关重要.

研究的目的:

报告碳水化合物的C3功能化和C1,C3非功能化的高效和立体选择性方法.
为具有挑战性的碳水化合物衍生物开发新型合成路径.
探索合成化合物的潜在应用和生物活动.

主要方法:

使用三乙醇 (TFE) 促进1,3-bis-induylation/2-nitroglycals的pyrrolylation.使用三乙醇 (TFE) 促进1,3-bis-induylation/pyrrolylation.使用三乙醇 (TFE) 促进2-nitroglycals的1,3-bis-induylation/pyrrolylation.使用三乙醇 (TFE) 促进2-nitroglycals的1,3-bis-induylation/pyrrolylation.使用三乙醇 (TFE) 促进2-nitroglycals的1,3-bis-induylation/pyrrolylation.
采用双功能氨基尿酸催化剂进行C3单替代.
对选择性C1和C3功能化的温度控制进行了研究.

主要成果:

在室温的1,3-bis-化/ pyrrolylation反应中达到高达93%的产量.
合成了80多种具有高立体选择性的挑战性糖衍生物 (在90%以上的实例中,单个异构体).
通过合成桥接的大环分子和格拉姆级反应,证明了潜在的应用.

结论:

开发了碳水化合物C3功能化和C1,C3非功能化的高效和立体选择性方法.
合成的碳水化合物衍生物对药物发现有前途,其中三种化合物表现出强大的抑制人类癌细胞.
该方法提供了各种复杂的碳水化合物结构,具有潜在的治疗应用.

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