N-(2-amino-4,5-dichlorophenyl)-2-ethoxy-4-cyanobenzamide | 316810-13-6

• 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: N-(2-amino-4,5-dichlorophenyl)-2-ethoxy-4-cyanobenzamide
• 英文别名: N-(2-amino-4,5-dichlorophenyl)-4-cyano-2-ethoxybenzamide
• CAS: 316810-13-6
• 化学式: C₁₆H₁₃Cl₂N₃O₂
• 分子量: 350.204
• InChiKey: YJABHZXVZVPOBH-UHFFFAOYSA-N

物化性质

• 熔点：
  195-198 °C
• 沸点：
  475.6±45.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  88.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-amino-4,5-dichlorophenyl)-2-ethoxy-4-cyanobenzamide 在 盐酸 、 sodium hydroxide 、 phosphorus pentoxide 作用下， 以 乙醇 、 xylene 为溶剂， 反应 49.0h， 生成 5,6-dichloro-2-(4-carboxy-2-ethoxyphenyl)benzimidazole hydrochloride
  参考文献：
  名称：

  Synthesis of photoactivable inhibitors of osteoclast vacuolar ATPase

  摘要：

  Amides of (2Z,4E)-5-[(5,6-dichloroindol-2-yl)]-2-methoxy-N-[3-[4-[3-(carboxymethoxy)phenyl)] piperazin-1-yl]propyl]-2,4-pentadienamide (1) and of 5-(5,6-dichloro-2-indolyl)-2-methoxy-2,4-pentadienoic acid (2) are strong inhibitors of the vacuolar ATPase located on the plasma membrane of osteoclasts. In order to understand which V-ATPase subunit is involved in the interaction with these novel inhibitors, analogues containing a photoactivable group and an iodine atom were designed. A series of alcohols or amines containing the photoactivable trifluoroaziridinophenyl or benzophenone moiety and an iodine atom were linked to the above acids via an ester or amide group. These compounds could be thereafter used as a radioactive photoprobe to label the protein. Whereas the compounds containing the photoactivable groups maintained good inhibitory activity, the introduction of the bulky iodine atom was generally detrimental, decreasing potency significantly. Better results were obtained by linking. 3-(4-amino-piperidinomethyl)-3'-iodobenzophenone to 3-ethoxy-4-(2-(5,6-dichlorobenzimidazolyl))benzoic acid to give the corresponding amide 27, that inhibited vacuolar ATP-ase with a IC50 = 140 nM. The feasibility of introducing a radioactive 1211 atom,was ascertained by exchanging the iodine with a tributylstannyl group, that was again substituted by iodine. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00106-8
• 作为产物：
  描述：

  4-氨基-2-乙氧基苯甲酸甲酯 在 盐酸 、 sodium hydroxide 、 氯化亚砜 、 三乙胺 、 sodium nitrite 作用下， 以 辛醇 、 二氯甲烷 、 水 为溶剂， 反应 27.0h， 生成 N-(2-amino-4,5-dichlorophenyl)-2-ethoxy-4-cyanobenzamide
  参考文献：
  名称：

  Synthesis of photoactivable inhibitors of osteoclast vacuolar ATPase

  摘要：

  Amides of (2Z,4E)-5-[(5,6-dichloroindol-2-yl)]-2-methoxy-N-[3-[4-[3-(carboxymethoxy)phenyl)] piperazin-1-yl]propyl]-2,4-pentadienamide (1) and of 5-(5,6-dichloro-2-indolyl)-2-methoxy-2,4-pentadienoic acid (2) are strong inhibitors of the vacuolar ATPase located on the plasma membrane of osteoclasts. In order to understand which V-ATPase subunit is involved in the interaction with these novel inhibitors, analogues containing a photoactivable group and an iodine atom were designed. A series of alcohols or amines containing the photoactivable trifluoroaziridinophenyl or benzophenone moiety and an iodine atom were linked to the above acids via an ester or amide group. These compounds could be thereafter used as a radioactive photoprobe to label the protein. Whereas the compounds containing the photoactivable groups maintained good inhibitory activity, the introduction of the bulky iodine atom was generally detrimental, decreasing potency significantly. Better results were obtained by linking. 3-(4-amino-piperidinomethyl)-3'-iodobenzophenone to 3-ethoxy-4-(2-(5,6-dichlorobenzimidazolyl))benzoic acid to give the corresponding amide 27, that inhibited vacuolar ATP-ase with a IC50 = 140 nM. The feasibility of introducing a radioactive 1211 atom,was ascertained by exchanging the iodine with a tributylstannyl group, that was again substituted by iodine. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00106-8

文献信息

• Azolylbenzamides and analogues and their use for treating osteoporosis
  申请人：Farina Carlo

  公开号：US20050038095A1

  公开（公告）日：2005-02-17

  A compound of formula (I) or a salt thereof, or a solvate thereof, wherein: X represents oxygen, sulphur, or NR b ; Y and Z each independently represent nitrogen, CH, CR 1 or CR 2 ; A represents an unsubstituted or substituted aryl group or an unsubstituted or substituted heterocyclyl group; R a represents —C(O)NR s R t ; R 1 and R 2 each independently represents hydrogen or specific substituents; and the use of such a compound in the treatment and/or prophylaxis of diseases associated with over activity of osteoclasts in mammals.

  式（I）的化合物或其盐或其溶剂化合物，其中：X代表氧、硫或NRb；Y和Z分别独立地代表氮、CH、CR1或CR2；A代表未取代或取代的芳基或未取代或取代的杂环基；R代表—C（O）NRsRt；R1和R2分别独立地代表氢或特定取代基；以及在治疗和/或预防与哺乳动物中成骨细胞过度活跃相关的疾病中使用这种化合物。
• AZOLYLBENZAMIDES AND ANALOGUES AND THEIR USE FOR TREATING OSTEOPOROSIS
  申请人：SMITHKLINE BEECHAM PLC

  公开号：EP1187813A1

  公开（公告）日：2002-03-20
• US7220769B2
  申请人：——

  公开号：US7220769B2

  公开（公告）日：2007-05-22
• [EN] AZOLYLBENZAMIDES AND ANALOGUES AND THEIR USE FOR TREATING OSTEOPOROSIS<br/>[FR] AZOLYLBENZAMIDE ET ANALOGUES ET LEUR UTILISATION POUR TRAITER L'OSTEOPOROSE
  申请人：SMITHKLINE BEECHAM PLC

  公开号：WO2001000587A1

  公开（公告）日：2001-01-04

  A compound of formula (I) or a salt thereof, or a solvate thereof, wherein: X represents oxygen, sulphur, or NRb; Y and Z each independently represent nitrogen, CH, CR1 or CR2; A represents an unsubstituted or substituted aryl group or an unsubstituted or substituted heterocyclyl group; Ra represents -C(O)NRsRt; R1 and R2 each independently represents hydrogen or specific substituents; and the use of such a compound in the treatment and/or prophylaxis of diseases associated with over activity of osteoclasts in mammals.