2-氨基-N-(4-甲基苯基)-4,5,6,7-四氢苯并噻吩-3-甲酰胺 | 83822-35-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-氨基-N-(4-甲基苯基)-4,5,6,7-四氢苯并噻吩-3-甲酰胺
• 英文名称: 2-amino-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid p-tolyl-amide
• 英文别名: 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid p-tolylamide；2-amino-4,5,6,7-tetrahydro-N-p-tolylbenzo[b]thiophene-3-carboxamide；2-amino-N-(4-methylphenyl)-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide
• CAS: 83822-35-9
• 化学式: C₁₆H₁₈N₂OS
• mdl: MFCD00421038
• 分子量: 286.398
• InChiKey: SGILTGZRNIXPNK-UHFFFAOYSA-N

物化性质

• 沸点：
  444.9±45.0 °C(Predicted)
• 密度：
  1.283±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 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-氨基-N-(4-甲基苯基)-4,5,6,7-四氢苯并噻吩-3-甲酰胺 在 盐酸 作用下， 以 1,4-二氧六环 、 溶剂黄146 为溶剂， 反应 13.0h， 生成 2-(Chloromethyl)-3-(4-methylphenyl)-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-one
  参考文献：
  名称：

  Manjunath, Kadthala Shekar; Mohan, Shamanna; Naragund, Laxmi Venkatesh Gurachar, Arzneimittel-Forschung/Drug Research, 1997, vol. 47, # 9, p. 1005 - 1008

  摘要：

  DOI：
• 作为产物：
  描述：

  α-(N-p-tolylcarboxamide)-α-cyclohexylidene acetonitrile 在 吗啉 、 1,2,3,4,5,6,7,8-八硫杂环辛烷 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以60 mg的产率得到2-氨基-N-(4-甲基苯基)-4,5,6,7-四氢苯并噻吩-3-甲酰胺
  参考文献：
  名称：

  Substituted 2-Acylaminocycloalkylthiophene-3-carboxylic Acid Arylamides as Inhibitors of the Calcium-Activated Chloride Channel Transmembrane Protein 16A (TMEM16A)

  摘要：

  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.

  DOI：

  10.1021/acs.jmedchem.7b00020

文献信息

• 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。
• Synthesis of some 3-substituted amino-4,5-tetramethylene thieno[2,3-d][ 1,2,3]-triazin-4(3H)-ones as potential antimicrobial agents
  作者：Janardhanan Saravanan、Shamanna Mohan、Jay Jyoti Roy

  DOI：10.1016/j.ejmech.2010.05.061

  日期：2010.9

  A series of 3-Substituted amino-4,5-tetramethylene thieno[2,3-d] [1,2,3]-triazine-4(3 (H) under bar )ones have been synthesized and characterized by UV,IR, 1H NMR, elemental and mass spectral analysis. The title compounds were evaluated for their antimicrobial activity by agar diffusion method against four bacteria and three fungi using Ampicillin and Miconazole nitrate as standards. The compounds Villa, IXa, Xa and XIa showed an antimicrobial efficacy considerably greater than the compounds la to Vila with -H, phenyl and electron donating (activating) groups like methyl, ethyl and tolyl substitutions at R. suggesting that lipophillic groups like chloro, fluoro substitution on the phenyl ring plays an important role in enhancing the antimicrobial properties of this class of compounds.From the screening results it can be concluded that the compounds having the lipophillic groups like chlorophenyl and fluorophenyl groups at R exhibited appreciable antimicrobial activities. Whereas, the compounds are having -H, phenyl and electron donating (activating) groups like methyl, ethyl and tolyl substituents at R were less active against all the organisms used. (C) 2010 Elsevier Masson SAS. All rights reserved.
• Schellhase; Bohm; Pech, Pharmazie, 1984, vol. 39, # 1, p. 19 - 21
  作者：Schellhase、Bohm、Pech

  DOI：——

  日期：——
• Bohm; Pech, Pharmazie, 1983, vol. 38, # 2, p. 136 - 137
  作者：Bohm、Pech

  DOI：——

  日期：——