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 | 126612-52-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 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
• 英文名称: 2-guanidino-N-(5-fluorobenzothiazol-2-yl)thiazole-4-carboxamide
• 英文别名: N-(5-Fluorobenzothiazol-2-yl)-2-guanidinothiazole-4-carboxamide；2-(diaminomethylideneamino)-N-(5-fluoro-1,3-benzothiazol-2-yl)-1,3-thiazole-4-carboxamide
• CAS: 126612-52-0
• 化学式: C₁₂H₉FN₆OS₂
• 分子量: 336.373
• InChiKey: MCYWZNLJNZNGAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  176
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-guanidinothiazole-4-carboxylic acid hydrochloride 在 N-甲基吡咯烷酮 、 对苯二酚 、 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， 反应 6.0h， 生成 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：

  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

• 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).
• 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：——
• 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.