α-(N-p-tolylcarboxamide)-α-cyclohexylidene acetonitrile | 89733-16-4

• 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: α-(N-p-tolylcarboxamide)-α-cyclohexylidene acetonitrile
• 英文别名: 2-cyano-2-cyclohexylidene-N-(4-methylphenyl)acetamide
• CAS: 89733-16-4
• 化学式: C₁₆H₁₈N₂O
• 分子量: 254.332
• InChiKey: CXPJLMJIVXMYKD-UHFFFAOYSA-N

物化性质

• 沸点：
  477.7±45.0 °C(Predicted)
• 密度：
  1.161±0.06 g/cm3(Predicted)

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：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  α-(N-p-tolylcarboxamide)-α-cyclohexylidene acetonitrile 在 sulfur 、 二乙胺 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 6.0h， 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：

  乙烷,三氯氟- 在 ammonium acetate 、 溶剂黄146 、 sodium sulfate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 α-(N-p-tolylcarboxamide)-α-cyclohexylidene acetonitrile
  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

• TETRAHYDROBENZOTHIOPHENE COMPOUND
  申请人：Astellas Pharma Inc.

  公开号：EP2565190A1

  公开（公告）日：2013-03-06

  The purpose is to provide a compound which has an intestinal phosphate transporter (NPT-IIb) inhibitory action and is useful as an active ingredient of an agent for treating and/or preventing hyperphosphatemia. A tetrahydrobenzothiophene compound of the following formula (I) has NPT-IIb inhibitory action and can be used as an agent for treating and/or preventing hyperphosphatemia: wherein, R1 represents -O-lower alkyl, -lower alkylene-phenyl, or the like; R2 and R3 are the same as or different from each other and represent H, lower alkyl, cycloalkyl, aryl, heteroaryl or the like, or, R2 and R3 may be combined with a nitrogen atom to which they bind to form 5- to 7-membered saturated cyclic amino; R4,s are the same as or different from each other and represent halogen, lower alkyl; and n represents 0 to 2.

  目的是提供一种化合物，该化合物具有抑制肠磷酸盐转运体（NPT-IIb）的作用，可用作治疗和/或预防高磷酸盐血症药物的活性成分。 下式（I）的四氢苯并噻吩化合物具有 NPT-IIb 抑制作用，可用作治疗和/或预防高磷酸盐血症的制剂： 其中，R1 代表-O-低级烷基、-低级亚烷基-苯基或类似物；R2 和 R3 彼此相同或不同，代表 H、低级烷基、环烷基、芳基、杂芳基或类似物，或者，R2 和 R3 可与它们结合的氮原子结合形成 5 至 7 元饱和环氨基；R4,s 彼此相同或不同，代表卤素、低级烷基；n 代表 0 至 2。
• 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：——
• SCHELLHASE, M.;BOEHM, R.;PECH, R., PHARMAZIE, 1984, 39, N 1, 19-21
  作者：SCHELLHASE, M.、BOEHM, R.、PECH, R.

  DOI：——

  日期：——