tert-butyl 2-amino-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxylate | 885115-88-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环七噻吩
• 英文名称: tert-butyl 2-amino-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxylate
• 英文别名: tert-butyl 2-amino-4H,5H,6H,7H,8H-cyclohepta[b]thiophene-3-carboxylate
• CAS: 885115-88-8
• 化学式: C₁₄H₂₁NO₂S
• mdl: MFCD02287899
• 分子量: 267.392
• InChiKey: DIOINDUDAISFQH-UHFFFAOYSA-N

物化性质

• 沸点：
  427.5±45.0 °C(Predicted)
• 密度：
  1.146±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.642
• 拓扑面积：
  80.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-amino-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxylate 在 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 2-(2,2,2-trifluoroacetamido)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of 2-acetamidothiophene-3-carboxamide derivatives against Leishmania donovani

  摘要：

  商业图书馆的高通量（HTS）和高内涵筛选（HCS）活动确定了 2-acetamidothophen-3-carboxamide 作为开发新型抗利什曼病药物的新型支架。进行了一系列化学修饰来研究构效关系（SAR），并使用细胞外前鞭毛体和细胞内无鞭毛体的生物测定来评估体外抗利什曼原虫活性。化合物 6a 对杜氏乳杆菌表现出良好的抗无鞭毛体活性 (EC50 = 6.41 μM)，而对人巨噬细胞没有任何细胞毒性 (CC50 > 50 μM)。

  DOI：

  10.1039/c3md00299c
• 作为产物：
  描述：

  氰乙酸叔丁酯 、 环庚酮 在 吗啉 、 sulfur 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 tert-butyl 2-amino-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxylate
  参考文献：
  名称：

  Synthesis and biological evaluation of 2-acetamidothiophene-3-carboxamide derivatives against Leishmania donovani

  摘要：

  商业图书馆的高通量（HTS）和高内涵筛选（HCS）活动确定了 2-acetamidothophen-3-carboxamide 作为开发新型抗利什曼病药物的新型支架。进行了一系列化学修饰来研究构效关系（SAR），并使用细胞外前鞭毛体和细胞内无鞭毛体的生物测定来评估体外抗利什曼原虫活性。化合物 6a 对杜氏乳杆菌表现出良好的抗无鞭毛体活性 (EC50 = 6.41 μM)，而对人巨噬细胞没有任何细胞毒性 (CC50 > 50 μM)。

  DOI：

  10.1039/c3md00299c

文献信息

• Design, Synthesis, in vitro Antiproliferative Activity Evaluation of 2-Acylaminothiopene-3-carboxamide Derivatives
  作者：Jie Tang、Jiefeng Zhang、Fengjie Guan、Jiakun Qiu、Yanfen Fang、Lifang Yu、Jingya Li、Fan Yang、Xiongwen Zhang、Jia Li

  DOI：10.3987/com-16-13558

  日期：——

  A series of 2-alkanoylamidothiophene-3-carboxamide derivatives were synthesized based on the hit compound 1. The anti-proliferative activity of all the compounds in vitro against MGC-803 (stomach) and HCT-116 (colon) cancer cell lines using SRB assays were tested. Several compounds showed improved anti-proliferative activity against MGC-803 and HCT-116. SAR study revealed that chlorine substituent in the 2-acetylamino part was important for anti-proliferative activity. 5a, 11b, 11c and lid were the most potent compounds against MGC-803 (IC(50)s = 2.32-2.95 mu M), and 5a and 11c also showed good anti-proliferative activity against HCT-116 cells (IC(50)s = 3.41-3.75 mu M). In addition, the anti-proliferative activity of llb and lid could be attributed to the apoptosis in HCT116 cells via caspase 3 activation, confirmed by flow cytometry assay and western blot analysis. Meanwhile, lib and lid decreased the mitochondrial membrane potential (MMP) in HCT116 cells.
• WO2006/44826
  申请人：——

  公开号：——

  公开（公告）日：——
• THIOPHENS AND THEIR USE AS ANTI-TUMOR AGENTS
  申请人：Compass Pharmaceuticals LLC

  公开号：EP1802634A2

  公开（公告）日：2007-07-04
• Thiophens and Their Use as Anti-Tumor Agents
  申请人：Ward John

  公开号：US20090143411A1

  公开（公告）日：2009-06-04

  The present invention provides novel compounds and pharmaceutical compositions thereof, as well as methods for using the compounds and pharmaceutical compositions for treating tumors. Examples of specific tumor types that the compounds may be used to treat include, but are not limited to sarcomas, melanomas, neuroblastomas, carcinomas (including but not limited to lung, renal cell, ovarian, liver, bladder, and pancreatic carcinomas), and mesotheliomas.
• US4692461A
  申请人：——

  公开号：US4692461A

  公开（公告）日：1987-09-08