2-amino-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid phenyl-amide | 60598-68-7

• 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-amino-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid phenyl-amide
• 英文别名: 2-amino-4,5,6,7-tetrahydro-N-phenylbenzo[b]thiophene-3-carboxamide；2-amino-N-phenyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide；2-amino-N-phenyl-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide
• CAS: 60598-68-7
• 化学式: C₁₅H₁₆N₂OS
• mdl: MFCD00425447
• 分子量: 272.371
• InChiKey: LQUUHYBNHKLHAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  83.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2-amino-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid phenyl-amide 在 吡啶 、 盐酸 、 氢氧化钾 、 一水合肼 、 三氯氧磷 、 三氯化磷 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 30.03h， 生成 4-phenyl-6,7,8,9-tetrahydro-<1>benzothieno<3,2-e><1,2,4>triazolo<4,3-a>pyrimidin-5(4H)-one
  参考文献：
  名称：

  Pathak, U S; Gandhi, N V; Singh, S, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1992, vol. 31, # 4, p. 223 - 229

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氰基乙酰苯胺 在 乙酸铵 、 sulfur 、 溶剂黄146 、 二乙胺 作用下， 以 乙醇 、 苯 为溶剂， 生成 2-amino-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid phenyl-amide
  参考文献：
  名称：

  Gadad, A K; Kumar, Hemant; Shishoo, C J, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1994, vol. 33, p. 298 - 301

  摘要：

  DOI：

文献信息

• NOVEL ANTI-CANCER COMPOUNDS
  申请人：KATHOLIEKE UNIVERSITEIT LEUVEN

  公开号：US20150126559A1

  公开（公告）日：2015-05-07

  The present invention relates to compounds having cytostatic activity against tumor cells. The compounds of the invention are of formula (I), or derivatives hereof, wherein R 0 , R 1 , R 2 , A, and X have defined meanings as described in claim 1 .

  本发明涉及具有抗肿瘤细胞细胞毒活性的化合物。本发明的化合物属于式(I)的化合物，或其衍生物，其中R0、R1、R2、A和X的定义如权利要求书中所述。
• Microwave‐Assisted Synthesis of 2‐Amino‐thiophene‐3‐Carboxylic Derivatives Under Solvent‐Free Conditions
  作者：Wei Huang、Jian Li、Jing Tang、Hong Liu、Jianhua Shen、Hualiang Jiang

  DOI：10.1081/scc-200057268

  日期：2005.5.1

  Abstract Under microwave irradiation and solvent‐free conditions, cyanoacetates (cyanoacetamides) react with ketones and sulphur in the presence of a small amount of morpholine to give 2‐amino‐thiophene‐3‐carboxylic derivatives. In particular, tetrahydro‐benzo[b]thiophene‐3‐carboxylic acid N‐aryl amides were synthesized in high yields of 84–95%.

  摘要 在微波辐射和无溶剂条件下，氰基乙酸酯（氰基乙酰胺）在少量吗啉存在下与酮和硫反应生成 2-氨基-噻吩-3-羧酸衍生物。特别是，四氢苯并[b]噻吩-3-羧酸N-芳基酰胺以84-95%的高产率合成。
• Barium aluminate nano-powders efficient catalyst for the synthesis of novel benzo[b]thiophene, thieno[2,3-c]thiopyran and thieno[2,3-c]pyridine derivatives
  作者：Hossein Yarahmadi、Majid Ghashang、Saeid Jabbar Zare、Alireza Khodaivandi

  DOI：10.1080/10426507.2017.1295961

  日期：2017.8.3

  aluminate (BaAl2O4) can be synthesized by a facile solution reaction at room temperature using barium and aluminum salts and 2-aminoethanol as a precipitating agent. The as-prepared sample showed a good reactivity in the synthesis of benzo[b]thiophene, thieno[2,3-c]thiopyran and thieno[2,3-c]pyridine derivatives. Comparatively the method is efficient and eco-friendly, and finally, a range of compounds with

  图形摘要摘要 铝酸钡 (BaAl2O4) 的均匀纳米粉末可以在室温下使用钡盐和铝盐以及 2-氨基乙醇作为沉淀剂通过简单的溶液反应合成。所制备的样品在苯并[b]噻吩、噻吩并[2,3-c]噻喃和噻吩并[2,3-c]吡啶衍生物的合成中显示出良好的反应性。相比之下，该方法高效且环保，最终可以以优异的收率获得一系列具有可变功能的化合物。
• Substituted 2-Acylaminocycloalkylthiophene-3-carboxylic Acid Arylamides as Inhibitors of the Calcium-Activated Chloride Channel Transmembrane Protein 16A (TMEM16A)
  作者：Eric C. Truong、Puay W. Phuan、Amanda L. Reggi、Loretta Ferrera、Luis J. V. Galietta、Sarah E. Levy、Alannah C. Moises、Onur Cil、Elena Diez-Cecilia、Sujin Lee、Alan S. Verkman、Marc O. Anderson

  DOI：10.1021/acs.jmedchem.7b00020

  日期：2017.6.8

  Transmembrane protein 16A (TMEM16A), also called anoctamin 1 (ANO1), is a calcium-activated chloride channel expressed widely mammalian cells, including epithelia, vascular smooth muscle tissue, electrically excitable cells, and some tumors. TMEM16A inhibitors have been proposed for treatment of disorders of epithelial fluid and mucus secretion, hypertension, asthma, and possibly cancer. Herein we report, by screening, the discovery of 2-acylaminocycloalkylthiophene-3-carboxylic acid arylamides (AACTs) as inhibitors of TMEM16A and analysis of 48 synthesized analogs (10ab-10bw) of the original AACT compound (10aa). Structure activity studies indicated the importance of benzene substituted as 2- or 4-methyl, or 4-fluoro, and defined the significance of thiophene substituents and size of the cycloalkylthiophene core. The most potent compound (10bm), which contains an unusual bromodifluoroacetamide at the thiophene 2-position, had IC50 of similar to 30 nM, similar to 3.6-fold more potent than the most potent previously reported TMEM16A inhibitor 4 (Ani9), and >10-fold improved metabolic stability. Direct and reversible inhibition of TMEM16A by 10bm was demonstrated by patch-clamp analysis. AACTs may be useful as pharmacological tools to study TMEM16A function and as potential drug development candidates.
• Shisoo; Devani; Ananthan, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1989, vol. 28, # 12, p. 1039 - 1047
  作者：Shisoo、Devani、Ananthan、Jain、Bhadti、Mohan、Patel

  DOI：——

  日期：——