2-guanidinothiazole-4-carboxylic acid succinimido ester hydrochloride | 126612-94-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-guanidinothiazole-4-carboxylic acid succinimido ester hydrochloride
• 英文别名: 2-guanidinothiazole-4-carboxylate N-hydroxysuccinimide ester hydrochloride；(2,5-Dioxopyrrolidin-1-yl) 2-(diaminomethylideneamino)-1,3-thiazole-4-carboxylate;hydrochloride
• CAS: 126612-94-0
• 化学式: C₉H₉N₅O₄S*ClH
• 分子量: 319.728
• InChiKey: JDSPQLKOCJYZTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.31
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  169
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-amino-5-fluorobenzothiazole hydrochloride 、 2-guanidinothiazole-4-carboxylic acid succinimido ester hydrochloride 在 对苯二酚 作用下， 以 various solvent(s) 为溶剂， 反应 6.0h， 以41%的产率得到2-(二氨基亚甲基氨基)-N-(5-氟-1,3-苯并噻唑-2-基)-1,3-噻唑-4-甲酰胺
  参考文献：
  名称：

  Quantitative structure-activity relationships of antitumor guanidinothiazolecarboxamides with survival enhancement for therapy in the 3LL Lewis lung carcinoma model

  摘要：

  Guanidinothiazolecarboxamides (GTCs) are a novel class of antitumor agents found to be systemically active against experimental pulmonary metastases of 3LL Lewis lung carcinoma. A series of substituted benzothiazole GTCs were found to produce enhancement of survival in this model by using 8 days of intraperitoneal dosing initiated 2 days after intravenous tumor challenge. Quantitative structure-activity relationships have been discovered in the GTC series with survival enhancement correlated to substituent parameters. Optimal correlations were found between the probit transform of the drug-induced increased lifespan (ILS) and field and pi parameters. Among the most effective analogues in this series was N-(5-fluorobenzothiazol-2-yl)-2-guanidinothiazole-4-carboxamide (19).

  DOI：

  10.1021/jm00111a009
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 2-guanidinothiazole-4-carboxylic acid hydrochloride 在 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以66%的产率得到2-guanidinothiazole-4-carboxylic acid succinimido ester hydrochloride
  参考文献：
  名称：

  N-(5-fluorobenzothiazol-2-yl)-2-guanidinothiazole-4-carboxamide. A novel, systemically active antitumor agent effective against 3LL Lewis Lung carcinoma

  摘要：

  N-(5-Fluorobenzothiazol-2-yl)-2-guanidinothiazole-4-carboxamide (1) is a member of a series of amides found to substantially increase lifespan in mice bearing established micrometastatic 3LL Lewis lung carcinoma. Amide 1 is effective after either oral or intraperitoneal dosing in acute, subacute, or chronic regimens. 1 is well tolerated in this model with an excellent therapeutic index relative to the cytotoxic anticancer drug adriamycin.

  DOI：

  10.1021/jm00107a007

文献信息

• Aromatic and heterocyclic carboxamide derivatives as antineoplastic agents
  申请人：PFIZER INC.

  公开号：EP0343893A1

  公开（公告）日：1989-11-29

  Acyl derivatives of 2-aminobenzothiazole and alkylated analogs thereof as antitumor agents.

  作为抗肿瘤药物的 2-氨基苯并噻唑酰基衍生物及其烷基化类似物。
• SCHNUR, RODNEY C.;FLIRI, ANTON F. J.;KAJIJI, SHAMA;POLLACK, VINCENT A., J. MED. CHEM., 34,(1991) N, C. 914-918
  作者：SCHNUR, RODNEY C.、FLIRI, ANTON F. J.、KAJIJI, SHAMA、POLLACK, VINCENT A.

  DOI：——

  日期：——
• US4970318A
  申请人：——

  公开号：US4970318A

  公开（公告）日：1990-11-13