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
• Quantitative structure-activity relationships of antitumor guanidinothiazolecarboxamides with survival enhancement for therapy in the 3LL Lewis lung carcinoma model
  作者：Rodney C. Schnur、Randall J. Gallaschun、David H. Singleton、Martin Grissom、Donald E. Sloan、Peter Goodwin、Patricia A. McNiff、Anton F. J. Fliri、F. Michael Mangano

  DOI：10.1021/jm00111a009

  日期：1991.7

  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).
• N-(5-fluorobenzothiazol-2-yl)-2-guanidinothiazole-4-carboxamide. A novel, systemically active antitumor agent effective against 3LL Lewis Lung carcinoma
  作者：Rodney C. Schnur、Anton F. J. Fliri、Shama Kajiji、Vincent A. Pollack

  DOI：10.1021/jm00107a007

  日期：1991.3

  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.