5-chloro-1-phenyl-1,3-dihydro-2H-benzimidazol-2-one | 79759-47-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 5-chloro-1-phenyl-1,3-dihydro-2H-benzimidazol-2-one
• 英文别名: 5-chloro-1-phenyl-1H-benzo[d]imidazol-2(3H)-one；6-chloro-3-phenyl-1H-benzimidazol-2-one
• CAS: 79759-47-0
• 化学式: C₁₃H₉ClN₂O
• 分子量: 244.68
• InChiKey: RMPWZHBFXOLXFG-UHFFFAOYSA-N

物化性质

• 熔点：
  223-225 °C(Solv: ethanol (64-17-5))
• 密度：
  1.372±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-chloro-1-phenyl-1,3-dihydro-2H-benzimidazol-2-one 在 苯膦酰二氯 、 一水合肼 作用下， 反应 24.0h， 生成 1-(5-chloro-1-phenyl-1H-benzo[d]imidazol-2-(3H)-ylidene)hydrazine
  参考文献：
  名称：

  3-Aryl-[1,2,4]triazino[4,3-a]benzimidazol-4(10H)-one: A Novel Template for the Design of Highly Selective A_2B Adenosine Receptor Antagonists

  摘要：

  In an effort to identify novel ligands possessing high affinity and selectivity for the A(2B) AR subtype, we further investigated the class of 3-aryl[1,2,4]triazino[4,3-a]benzimidazol-4(10H)-ones V, previously disclosed by us as selective A(1) AR antagonists. Preliminary assays on a number of triazinobenzimidazoles derived from our "in-house" collection revealed that all the derivatives selected showed significant affinity at A(2B) AR, no affinity at A(3) AR, and various degrees of selectivity toward A(1) and A(2A) ARs. Investigation of a new series featuring modified substituents at the 10-position (4'-chlorophenyl or phenylethyl groups), and a chlorine atom at the 7-position (X) of the triazinobenzimidazole nucleus, yielded highly potent and selective A(2B) AR antagonists. The presence of a pendant 3-phenyl ring appears to hamper the interaction with A(2A) AR, conferring high A(2B)/A(2A) AR selectivity. Derivative 13 (X = Cl, R = C6H5) is the most potent and selective compound, with an IC50 of 3.10 nM at A(2B) AR and no affinity at A(1), A(2A), and A(3) ARs.

  DOI：

  10.1021/jm201177b
• 作为产物：
  描述：

  (5-氯-2-(苯基氨基)苯基)氨基甲酸乙酯 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以99%的产率得到5-chloro-1-phenyl-1,3-dihydro-2H-benzimidazol-2-one
  参考文献：
  名称：

  Bianchi; Butti; Rossi, European Journal of Medicinal Chemistry, 1981, vol. 16, # 4, p. 321 - 326

  摘要：

  DOI：

文献信息

• Tissue non-specific alkaline phosphatase inhibitors and uses thereof for treating vascular calcification
  申请人：Burnham Institute for Medical Research

  公开号：EP2433496A1

  公开（公告）日：2012-03-28

  Disclosed herein are compounds that are tissue-nonspecific alkaline phosphatase inhibitors. The disclosed compounds are used to treat, prevent, or abate vascular calcification, arterial calcification and other cardiovascular diseases.

  本文公开的化合物是组织非特异性碱性磷酸酶抑制剂。所公开的化合物可用于治疗、预防或减轻血管钙化、动脉钙化和其他心血管疾病。
• 3-Aryl-[1,2,4]triazino[4,3-<i>a</i>]benzimidazol-4(10<i>H</i>)-one: A Novel Template for the Design of Highly Selective A_2B Adenosine Receptor Antagonists
  作者：Sabrina Taliani、Isabella Pugliesi、Elisabetta Barresi、Francesca Simorini、Silvia Salerno、Concettina La Motta、Anna Maria Marini、Barbara Cosimelli、Sandro Cosconati、Salvatore Di Maro、Luciana Marinelli、Simona Daniele、Maria Letizia Trincavelli、Giovanni Greco、Ettore Novellino、Claudia Martini、Federico Da Settimo

  DOI：10.1021/jm201177b

  日期：2012.2.23

  In an effort to identify novel ligands possessing high affinity and selectivity for the A(2B) AR subtype, we further investigated the class of 3-aryl[1,2,4]triazino[4,3-a]benzimidazol-4(10H)-ones V, previously disclosed by us as selective A(1) AR antagonists. Preliminary assays on a number of triazinobenzimidazoles derived from our "in-house" collection revealed that all the derivatives selected showed significant affinity at A(2B) AR, no affinity at A(3) AR, and various degrees of selectivity toward A(1) and A(2A) ARs. Investigation of a new series featuring modified substituents at the 10-position (4'-chlorophenyl or phenylethyl groups), and a chlorine atom at the 7-position (X) of the triazinobenzimidazole nucleus, yielded highly potent and selective A(2B) AR antagonists. The presence of a pendant 3-phenyl ring appears to hamper the interaction with A(2A) AR, conferring high A(2B)/A(2A) AR selectivity. Derivative 13 (X = Cl, R = C6H5) is the most potent and selective compound, with an IC50 of 3.10 nM at A(2B) AR and no affinity at A(1), A(2A), and A(3) ARs.
• BIANCHI, M.;BUTTI, A.;ROSSI, S.;BARZAGHI, F.;MARCARIA, V., EUR. J. MED. CHEM.-CHIM. THER., 1981, 16, N 4, 321-326
  作者：BIANCHI, M.、BUTTI, A.、ROSSI, S.、BARZAGHI, F.、MARCARIA, V.

  DOI：——

  日期：——
• TISSUE NON-SPECIFIC ALKALINE PHOSPHATASE INHIBITORS AND USES THEREOF FOR TREATING VASCULAR CALCIFICATION
  申请人：The Burnham Institute for Medical Research

  公开号：EP2164329A2

  公开（公告）日：2010-03-24
• US8119693B2
  申请人：——

  公开号：US8119693B2

  公开（公告）日：2012-02-21