3-hydroxy-2-{[4-(4,5,6,7-tetrachloro-1,3-dioxo-1,3-dihydroisoindole-2-sulfonyl)phenyl]hydrazono}-3-(thiazol-2-ylamino)propionic acid methyl ester | 1142922-95-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 3-hydroxy-2-{[4-(4,5,6,7-tetrachloro-1,3-dioxo-1,3-dihydroisoindole-2-sulfonyl)phenyl]hydrazono}-3-(thiazol-2-ylamino)propionic acid methyl ester
• CAS: 1142922-95-9
• 化学式: C₂₁H₁₁Cl₄N₅O₇S₂
• 分子量: 651.292
• InChiKey: PFLVAHZGXKVKSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  39.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  164.2
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  methyl 2-(2-(p-sulphonamidophenyl)hydrazono)-2-(thiazol-2-ylcarbamoyl)acetate 、 四氯苯二甲酸酐 在 溶剂黄146 作用下， 反应 6.0h， 以77%的产率得到3-hydroxy-2-{[4-(4,5,6,7-tetrachloro-1,3-dioxo-1,3-dihydroisoindole-2-sulfonyl)phenyl]hydrazono}-3-(thiazol-2-ylamino)propionic acid methyl ester
  参考文献：
  名称：

  Synthesis and reactions of thiosemicarbazides, triazoles, and Schiff bases as antihypertensive α-blocking agents

  摘要：

  Methyl 2-(thiazol-2-ylcarbamoyl)acetate was synthesized and used as starting material. It was treated with hydrazine hydrate to afford the hydrazide, which was reacted with nitromethane and formaldehyde to give the saturated nitropyrimidine. The hydrazide was reacted with phenyl isothiocyanate to afford the thiosemicarbazide, which was cyclized with ethyl bromoacetate, sodium hydroxide, or sulfuric acid to afford N-phenylthiazolidinone, N-phenyltriazole, and thiadiazolyl derivatives. The methyl 2-(thiazol-2-ylcarbamoyl)acetate was coupled with diazonium salts of aniline, 4-chloroaniline, 4-bromoaniline, or 4-aminobenzenesulfonamide to afford the carbamoyl acetates, which were reacted with 2-aminobenzimidazole, 1,2,4,5-tetrachlorophthalic anhydride, and hydrazine hydrate to afford the corresponding thiazolylmalonamide, tetrachloroisoindolylimide, and tri-azole derivatives. Schiff bases and imides are newly synthesized candidates obtained via simple condensation of the hydrazide with aldehydes, 2,3-pyridinedicarboxylic anhydride, or 1,8-naphthalenedicarboxylic anhydride. The pharmacological screening showed that many of these compounds have good antihypertensive alpha-blocking activity and low toxicity.

  DOI：

  10.1007/s00706-008-0896-2

文献信息

• Synthesis and reactions of thiosemicarbazides, triazoles, and Schiff bases as antihypertensive α-blocking agents
  作者：Bakr F. Abdel-Wahab、Salwa F. Mohamed、Abd El-Galil E. Amr、Mohamed M. Abdalla

  DOI：10.1007/s00706-008-0896-2

  日期：2008.9

  Methyl 2-(thiazol-2-ylcarbamoyl)acetate was synthesized and used as starting material. It was treated with hydrazine hydrate to afford the hydrazide, which was reacted with nitromethane and formaldehyde to give the saturated nitropyrimidine. The hydrazide was reacted with phenyl isothiocyanate to afford the thiosemicarbazide, which was cyclized with ethyl bromoacetate, sodium hydroxide, or sulfuric acid to afford N-phenylthiazolidinone, N-phenyltriazole, and thiadiazolyl derivatives. The methyl 2-(thiazol-2-ylcarbamoyl)acetate was coupled with diazonium salts of aniline, 4-chloroaniline, 4-bromoaniline, or 4-aminobenzenesulfonamide to afford the carbamoyl acetates, which were reacted with 2-aminobenzimidazole, 1,2,4,5-tetrachlorophthalic anhydride, and hydrazine hydrate to afford the corresponding thiazolylmalonamide, tetrachloroisoindolylimide, and tri-azole derivatives. Schiff bases and imides are newly synthesized candidates obtained via simple condensation of the hydrazide with aldehydes, 2,3-pyridinedicarboxylic anhydride, or 1,8-naphthalenedicarboxylic anhydride. The pharmacological screening showed that many of these compounds have good antihypertensive alpha-blocking activity and low toxicity.