2-benzamido-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide | 19819-17-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-benzamido-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide
• 英文别名: 2-benzamido-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide
• CAS: 19819-17-1
• 化学式: C₁₆H₁₆N₂O₂S
• mdl: MFCD00416486
• 分子量: 300.381
• InChiKey: ZYIMILUMMMUVLQ-UHFFFAOYSA-N

物化性质

• 溶解度：
  0.8 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  100
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-benzamido-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide 在 对甲苯磺酸 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 3.75h， 生成 N,2-diphenyl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-amine
  参考文献：
  名称：

  Anti-tubercular activities of 5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3- d ]pyrimidin-4-amine analogues endowed with high activity toward non-replicative Mycobacterium tuberculosis

  摘要：

  Thirty three derivatives of 2-substituted 5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-amine analogues were synthesized by molecular modification of a reported antimycobacterial molecule (GSK163574A). Compounds were evaluated in vitro against actively replicative and nutrient starved non-replicative Mycobacterium tuberculosis (MTB), enzymatic screening and cytotoxicity against RAW 264.7 cell line. Among the compounds, 2-ethyl-N-phenethy1-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d] pyrimidin-4-amine (5c) was found to be the most active compound against non-replicative MTB with 2.7 log reduction of bacteria at 10 mu g/mL and was more potent than isoniazid (1.2 log reduction) and rifampicin (2.0 log reduction) at same dose level. Compound 5c also showed activity against MTB alanine dehydrogenase enzyme with IC50 of 1.82 +/- 0.42 mu M and showed 25% cytotoxicity against RAW 264.7 cell line at 50 mu g/mL. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.09.012
• 作为产物：
  描述：

  环己酮 在 吗啉 、 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-benzamido-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide
  参考文献：
  名称：

  Discovery of novel tetrahydrobenzothiophene derivatives as MSBA inhibitors for antimicrobial agents

  摘要：

  DOI：

  10.1016/j.bioorg.2023.106932

文献信息

• Utility of a 2-aminothiophene-3-carboxamide in the synthesis of thienopyridines and thienopyrimidines
  作者：Rafat M. Mohareb、Sherif M. Sherif、Hatem M. Gaber、Sami S. Ghabrial、Susan I. Aziz

  DOI：10.1002/hc.10179

  日期：——

  2-Amino-4,5,6,7-tetrahydrobenzo[b]- thiophene-3-carboxamide (1) was prepared according to Gewald procedure. Its reactivity toward a variety of chemical reagents was studied to give thienopyridines and -pyrimidines. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:459–467, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10179

  2-氨基-4,5,6,7-四氢苯并[b]-噻吩-3-甲酰胺(1)根据Gewald程序制备。研究了它对多种化学试剂的反应性以得到噻吩并吡啶和嘧啶。© 2003 Wiley Periodicals, Inc. 杂原子化学 14:459–467, 2003; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.10179
• Heterobicyclic Compounds as Pharmaceutically Active Agents
  申请人：Koul Anil

  公开号：US20070275962A1

  公开（公告）日：2007-11-29

  Described are heterobicyclic compounds such as 4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid amides, 4,7-dihydro-5H-thieno[2,3-c]thiopyran 3-carboxylic acid amides, 4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid amides, or benzo[b]thiophene-3-carboxylic acid amides and pharmaceutically acceptable salts thereof, the use of these derivatives for the prophylaxis and/or treatment of various diseases such as infectious diseases, including mycobacteriainduced infections and opportunistic diseases, prion diseases, immunological diseases, autoimmune diseases, bipolar and clinical disorders, cardiovascular diseases, cell proliferative diseases, diabetes, inflammation, transplant rejections, erectile dysfunction, neurodegenerative diseases and stroke, as well as compositions containing at least one heterobicyclic compound and/or pharmaceutically acceptable salts thereof. Furthermore, reaction procedures for the synthesis of the heterobicyclic compound are disclosed.

  本文介绍了异杂双环化合物，例如4,5,6,7-四氢苯并[b]噻吩-3-羧酸酰胺，4,7-二氢-5H-噻吩[2,3-c]硫杂吡喃-3-羧酸酰胺，4,7-二氢-5H-噻吩[2,3-c]吡喃-3-羧酸酰胺，或苯并[b]噻吩-3-羧酸酰胺及其药学上可接受的盐。这些衍生物的用途包括预防和/或治疗各种疾病，如传染性疾病，包括分支杆菌感染和机会性疾病，朊病，免疫性疾病，自身免疫性疾病，双相和临床障碍，心血管疾病，细胞增殖性疾病，糖尿病，炎症，移植排斥，勃起功能障碍，神经退行性疾病和中风，以及含有至少一种异杂双环化合物和/或药学上可接受的盐的组合物。此外，还公开了合成异杂双环化合物的反应程序。
• COMPOUNDS FOR TREATING PROTEIN FOLDING DISORDERS
  申请人：Tait Bradley

  公开号：US20130072473A1

  公开（公告）日：2013-03-21

  The present invention is directed to compounds of Formulae (I), (IIa-IIh), (IIIa-IIIe), (IVa-IVc), (Va-V1), (VIa-VII), (VII), (VIII) and (IX), pharmaceutical compositions thereof and methods of use thereof in the treatment of conditions associated with a dysfunction in proteostasis.

  本发明涉及式(I)、(IIa-IIh)、(IIIa-IIIe)、(IVa-IVc)、(Va-V1)、(VIa-VII)、(VII)、(VIII)和(IX)化合物，以及其制备的药物组合物和治疗与蛋白质稳态失调相关疾病的方法。
• Identification of 2-acylaminothiophene-3-carboxamides as potent inhibitors of FLT3
  作者：Raymond J. Patch、Christian A. Baumann、Jian Liu、Alan C. Gibbs、Heidi Ott、Jennifer Lattanze、Mark R. Player

  DOI：10.1016/j.bmcl.2006.03.032

  日期：2006.6

  A series of 2-acylaminothiophene-3-carboxamides has been identified which exhibit potent inhibitory activity against the FLT3 tyrosine kinase. Compound 44 inhibits the isolated enzyme (IC50 = 0.027 mu M) and blocks the proliferation of MV4-11 cells (IC50 = 0.41 mu M). Structure activity relationship studies within this series are described in the context of a proposed binding model within the ATP binding site of the enzyme. (c) 2006 Elsevier Ltd. All rights reserved.
• KONNO, SHOETSU;TSUNODA, MAMORU;WATANABE, RYO;YAMANAKA, HIROSHI;FUJITA, FU+, YAKUGAKU DZASSI, 109,(1989) N, S. 464-473
  作者：KONNO, SHOETSU、TSUNODA, MAMORU、WATANABE, RYO、YAMANAKA, HIROSHI、FUJITA, FU+

  DOI：——

  日期：——