1-(2-Diaethylaminoaethyl)-2-benzimidazolinon | 88858-07-5

• 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: 1-(2-Diaethylaminoaethyl)-2-benzimidazolinon
• 英文别名: 2-Oxo-1-(2-diethylamino-ethyl)-benzimidazolin；1-(2-diethylamino-ethyl)-1,3-dihydro-benzoimidazol-2-one；1-(2-(Diethylamino)ethyl)-1H-benzo[d]imidazol-2(3H)-one；3-[2-(diethylamino)ethyl]-1H-benzimidazol-2-one
• CAS: 88858-07-5
• 化学式: C₁₃H₁₉N₃O
• 分子量: 233.313
• InChiKey: DCLKFMYMURBJDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  35.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[(2,4-二氯苯氧基)甲基]环氧乙烷 、 1-(2-Diaethylaminoaethyl)-2-benzimidazolinon 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-[3-(2,4-Dichlorophenoxy)-2-hydroxypropyl]-3-[2-(diethylamino)ethyl]benzimidazol-2-one
  参考文献：
  名称：

  Acinetobacter baumannii OxPhos inhibitors as selective anti-infective agents

  摘要：

  The Gram-negative bacterium Acinetobacter baumannii is an opportunistic pathogen in humans and infections are poorly treated by current therapy. Recent emergence of multi-drug resistant strains and the lack of new antibiotics demand an immediate action for development of new anti-Acinetobacter agents. To this end, oxidative phosphorylation (OxPhos) was identified as a novel target for drug discovery research. Consequently, a library of similar to 10,000 compounds was screened using a membrane-based ATP synthesis assay. One hit identified was the 2-iminobenzimidazole 1 that inhibited the OxPhos of A. baumannii with a modestly high selectivity against mitochondrial OxPhos, and displayed an MIC of 25 mu M (17 mu g/mL) against the pathogen. The 2-iminobenzimidazole 1 was found to inhibit the type 1 NADH-quinone oxidoreductase (NDH-1) of A. baumannii OxPhos by a biochemical approach. Among various derivatives that were synthesized to date, des-hydroxy analog 5 is among the most active with a relatively tight SAR requirement for the N'-aminoalkyl side chain. Analog 5 also showed less cytotoxicity against NIH3T3 and HepG2 mammalian cell lines, demonstrating the potential for this series of compounds as anti-Acinetobacter agents. Additional SAR development and target validation is underway. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.11.020
• 作为产物：
  描述：

  2-溴-N,N-二乙基乙胺氢溴酸 、 1-乙酰基-1,3-二氢-2H-苯并咪唑-2-酮 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-(2-Diaethylaminoaethyl)-2-benzimidazolinon
  参考文献：
  名称：

  Acinetobacter baumannii OxPhos inhibitors as selective anti-infective agents

  摘要：

  The Gram-negative bacterium Acinetobacter baumannii is an opportunistic pathogen in humans and infections are poorly treated by current therapy. Recent emergence of multi-drug resistant strains and the lack of new antibiotics demand an immediate action for development of new anti-Acinetobacter agents. To this end, oxidative phosphorylation (OxPhos) was identified as a novel target for drug discovery research. Consequently, a library of similar to 10,000 compounds was screened using a membrane-based ATP synthesis assay. One hit identified was the 2-iminobenzimidazole 1 that inhibited the OxPhos of A. baumannii with a modestly high selectivity against mitochondrial OxPhos, and displayed an MIC of 25 mu M (17 mu g/mL) against the pathogen. The 2-iminobenzimidazole 1 was found to inhibit the type 1 NADH-quinone oxidoreductase (NDH-1) of A. baumannii OxPhos by a biochemical approach. Among various derivatives that were synthesized to date, des-hydroxy analog 5 is among the most active with a relatively tight SAR requirement for the N'-aminoalkyl side chain. Analog 5 also showed less cytotoxicity against NIH3T3 and HepG2 mammalian cell lines, demonstrating the potential for this series of compounds as anti-Acinetobacter agents. Additional SAR development and target validation is underway. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.11.020

文献信息

• SUBSTITUTED BENZIMIDAZOL-2-ONES AS VASOPRESSIN RECEPTOR ANTAGONISTS AND NEUROPEPTIDE Y MODULATORS
  申请人：Ortho-McNeil Pharmaceutical, Inc.

  公开号：EP1330451A2

  公开（公告）日：2003-07-30
• US5162318A
  申请人：——

  公开号：US5162318A

  公开（公告）日：1992-11-10
• [EN] NOVEL SUBSTITUTED BENZIMIDAZOL-2-ONES AS VASOPRESSIN RECEPTOR ANTAGONISTS AND NEUROPEPTIDE Y MODULATORS<br/>[FR] NOUVELLES BENZIMIDAZOL-2-ONES SUBSTITUEES UTILISEES COMME ANTAGONISTES DU RECEPTEUR DE LA VASOPRESSINE ET COMME MODULATEURS DU NEUROPEPTIDE Y
  申请人：ORTHO MCNEIL PHARM INC

  公开号：WO2002055514A2

  公开（公告）日：2002-07-18

  The invention is directed to substituted benzimidazol-2-ones of Formula (I), wherein A, X, Y, m, n, R1, R2, R3, R4, and R5 are as described in the specification, which are useful as vasopressin receptor antagonists or Neuropeptide Y Modulators for treating conditions such as aggression, obsessive-compulsive disorders, hypertension, dysmenorrhea, congestive heart failure/cardiac insufficiency, coronary vasospasm, cardiac ischemia, liver cirrhosis, renal vasospasm, renal failure, edema, ischemia, stroke, thrombosis, water retention, nephrotic syndrome, central nervous injuries, obesity, anorexia, hyperglycemia, diabetes, anxiety, depression, asthma, memory loss, sexual dysfunction, disorders of sleep and other circadian rhythms, and Cushing's disease.
• [EN] 1-(3-PHENYLOXYPROPYL)PIPERIDINE DERIVATIVES<br/>[FR] DERIVES DE 1-(3-PHENYLOXYPROPYL)PIPERIDINE
  申请人：AKZO NOBEL NV

  公开号：WO2002100861A1

  公开（公告）日：2002-12-19

  The present invention relates to 1(3-phenyloxypropyl)-piperidine derivative having general Formula (I), wherein R1 is (C1-6)alkyl or (C4-8)cycloalkyl or phenyl, optionally substituted with (C1-6)alkyl, (C1-6)alkyloxy or halogen; R2 is H or (C1-6)alkyl; or R1 and R2 form together with the carbon atom to which they are bound (C4-8)cycloalkyl, optionally substitutes with (C1-6)alkyloxy or halogen; R3 is H, OH, (C1-6)alkyloxy or (C1-6)alkylcarbonyloxy; R4 represents 1-5 substituents independently selected from H, (C1-6)alkyl, (C1-6)alkyloxy and halogen; Y represents (a), (b) and Z is H; or Y and Z together with the carbon atom to which they are bound represent the spiro atom in the spiro atom in the spiro system formed with (c) *represents the spiro carbon atom; R6 is H, (C1-6)alkyl or (CO)n-(CH2)m-R12; n is 0 or 1; m is 1-4; R8 and R10 are independently H or(C1-6)alkyl; R7, R9 and R11 are independently H, (C1-6)alkyl, (C1-6)alkyloxy or halogen; R12 is hydroxy, (C1-4)alkyloxy, (C1-4)alkylthio, (C1-4)alkyloxycarbonyl, (C1-4)alkylcarbonyloxy, 2-tetrahydrofuranyl, 4-morpholinyl or di(C1-4)alkylamino; or a pharmaceutically acceptable salt thereof. The present invention also relates to pharmaceutical compositions comprising said derivatives, as well as to the use of these 1-(3-phenyloxypropyl)-piperidine derivatives in therapy.
• Acinetobacter baumannii OxPhos inhibitors as selective anti-infective agents
  作者：Harvey Rubin、Trevor Selwood、Takahiro Yano、Damian G. Weaver、H. Marie Loughran、Michael J. Costanzo、Richard W. Scott、Jay E. Wrobel、Katie B. Freeman、Allen B. Reitz

  DOI：10.1016/j.bmcl.2014.11.020

  日期：2015.1

  The Gram-negative bacterium Acinetobacter baumannii is an opportunistic pathogen in humans and infections are poorly treated by current therapy. Recent emergence of multi-drug resistant strains and the lack of new antibiotics demand an immediate action for development of new anti-Acinetobacter agents. To this end, oxidative phosphorylation (OxPhos) was identified as a novel target for drug discovery research. Consequently, a library of similar to 10,000 compounds was screened using a membrane-based ATP synthesis assay. One hit identified was the 2-iminobenzimidazole 1 that inhibited the OxPhos of A. baumannii with a modestly high selectivity against mitochondrial OxPhos, and displayed an MIC of 25 mu M (17 mu g/mL) against the pathogen. The 2-iminobenzimidazole 1 was found to inhibit the type 1 NADH-quinone oxidoreductase (NDH-1) of A. baumannii OxPhos by a biochemical approach. Among various derivatives that were synthesized to date, des-hydroxy analog 5 is among the most active with a relatively tight SAR requirement for the N'-aminoalkyl side chain. Analog 5 also showed less cytotoxicity against NIH3T3 and HepG2 mammalian cell lines, demonstrating the potential for this series of compounds as anti-Acinetobacter agents. Additional SAR development and target validation is underway. (C) 2014 Elsevier Ltd. All rights reserved.