HYPOGLYCEMIC ACTIVITY IN RELATION TO CHEMICAL STRUCTURE OF POTENTIAL ORAL ANTIDIABETIC SUBSTANCES. III. 2-BENZENESULFONAMIDO-5-ALKYL-1,3,4- THIADIAZOLES AND -OXADIAZOLES.
HYPOGLYCEMIC ACTIVITY IN RELATION TO CHEMICAL STRUCTURE OF POTENTIAL ORAL ANTIDIABETIC SUBSTANCES. III. 2-BENZENESULFONAMIDO-5-ALKYL-1,3,4- THIADIAZOLES AND -OXADIAZOLES.
复制标题
与潜在口服抗糖尿病物质的化学结构相关的降血糖活性。
DOI：
10.1021/jm01237a004
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发表时间：
1962
影响因子：
7.3
通讯作者：
A. Jonsson
中科院分区：
文献类型：
--
作者：
B. Hokfelt;A. Jonsson
对 2-(对氨基苯磺酰胺基-5-异丙基-1, 3, 4-噻二唑2) 降血糖活性的早期研究表明，降血糖活性通常由大量相关的磺胺基烷基噻二唑发挥。在具有包含 3 至 5 个碳原子的烷基的化合物中发现了最佳活性。 3, 4-噻二唑失活，使得 Bovet 和 Dubost2 得出结论，对氨基是这一系列化合物中降血糖活性的先决条件。在我们使用一般类型 RS02XHCOXHR' 的降血糖磺酰脲衍生物的实验中，我们获得了证据，表明分子的中间 (S02XHC0XH) 部分有非常特殊的结构要求，但端基 R 和 R' 可能会有所不同。在相当宽的范围内；例如，卡丁酰胺中的对氨基基团并不是必需的，因此我们想到类似的条件可能适用于噻二唑衍生物，因此我们开始研究其中有取代基的许多此类化合物。
Early investigations ofthe hypoglycemic activity of 2-(p-aminobenzenesulfonamido-5-isopropyl-l, 3, 4-thiadiazole2 revealed that hypoglycemic activity was generally exerted by a great number of related sulfanilamidoalkylthiadiazoles. Optimal activity was found in com-pounds possessing an alkyl group comprising three to five carbon atoms. The finding that 2-benzenesulfonamido-5-isopropyl-l, 3, 4-thiadiazole was inactive made Bovet and Dubost2conclude that the p-amino group was a prerequisite for hypoglycemic activity in this series of compounds. During our experiments3· 4 with hypoglycemic sulfonyl urea derivatives of the general type RS02XHCOXHR'we had obtained evidence that there are very specific structural requirements on the middle (S02XHC0XH) section of the molecule but that the end groups R and R'may vary within fairly wide limits; the p-amino group in carbutamide, eg, is by no means essential. It therefore occurred to us that similarconditions might hold true for the thiadiazole derivatives. Consequently we started the investigation of a number of such compounds in which the substituent