trans-toluene-4-sulfonic acid 3-(4-nitro-imidazol-1-yl)-cyclobutyl ester

• 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: trans-toluene-4-sulfonic acid 3-(4-nitro-imidazol-1-yl)-cyclobutyl ester
• 英文别名: [3-(4-nitroimidazol-1-yl)cyclobutyl] 4-methylbenzenesulfonate
• 化学式: C₁₄H₁₅N₃O₅S
• 分子量: 337.356
• InChiKey: IHKFZLVXBRHARG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  trans-toluene-4-sulfonic acid 3-(4-nitro-imidazol-1-yl)-cyclobutyl ester 以 乙醇 、 氯仿 、 水 为溶剂， 以2.2 g (99%)的产率得到1-(3-cis-azido-cyclobutyl)-4-nitro-1H-imidazole
  参考文献：
  名称：

  Imidazole derivatives

  摘要：

  该发明提供了公式11中的化合物，其中R1、R2、R3和R4的定义如下，并且它们的药用盐。公式1的化合物被指示具有抑制cdk5、cdk2和GSK-3活性。包括公式1的化合物的制药组合物和方法用于治疗和预防包括异常细胞生长的疾病和症状，如癌症，神经退行性疾病和受多巴胺神经传递影响的疾病和症状。还描述了包括公式1的化合物的制药组合物和方法，用于治疗男性生育能力和精子活力；糖尿病；糖耐量受损；代谢综合征或X综合征；多囊卵巢综合征；脂肪生成和肥胖；肌肉生成和虚弱，例如与年龄相关的体能下降；急性肌肉萎缩，例如与烧伤、卧床休息、肢体固定或主要胸部、腹部和/或骨科手术相关的肌肉萎缩和/或虚脱；败血症；脱发、头发变薄和秃头；以及免疫缺陷。

  公开号：

  US20020119963A1
• 作为产物：
  描述：

  对甲苯磺酰氯 、 3-(4-硝基-1H-咪唑-1-基)环丁醇 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以39%的产率得到trans-toluene-4-sulfonic acid 3-(4-nitro-imidazol-1-yl)-cyclobutyl ester
  参考文献：
  名称：

  Potent and cellularly active 4-aminoimidazole inhibitors of cyclin-dependent kinase 5/p25 for the treatment of Alzheimer’s disease

  摘要：

  Utilizing structure-based drug design, a 4-aminoimidazole heterocyclic core was synthesized as a replacement for a 2-aminothiazole due to potential metabolically mediated toxicity. The synthetic route utilized allowed for ready synthesis of 1-substituted-4-aminoimidazoles. SAR exploration resulted in the identification of a novel cis-substituted cyclobutyl group that gave improved enzyme and cellular potency against cdk5/p25 with up to 30-fold selectivity over cdk2/cyclin E. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.08.019

文献信息

• Imidazole derivatives
  申请人：——

  公开号：US20020119963A1

  公开（公告）日：2002-08-29

  The invention provides compounds of formula 1 1 wherein R 1 , R 2 , R 3 , and R 4 are as defined, and their pharmaceutically acceptable salts. Compounds of formula 1 are indicated to have activity inhibiting cdk5, cdk2, and GSK-3. Pharmaceutical compositions and methods comprising compounds of formula 1 for treating and preventing diseases and conditions comprising abnormal cell growth, such as cancer, and neurodegenerative diseases and conditions and those affected by dopamine neurotransmission. Also described are pharmaceutical compositions and methods comprising compounds of formula 1 for treating male fertility and sperm motility; diabetes mellitus; impaired glucose tolerance; metabolic syndrome or syndrome X; polycystic ovary syndrome; adipogenesis and obesity; myogenesis and frailty, for example age-related decline in physical performance; acute sarcopenia, for example muscle atrophy and/or cachexia associated with burns, bed rest, limb immobilization, or major thoracic, abdominal, and/or orthopedic surgery; sepsis; hair loss, hair thinning, and balding; and immunodeficiency.

  该发明提供了公式11中的化合物，其中R1、R2、R3和R4的定义如下，并且它们的药用盐。公式1的化合物被指示具有抑制cdk5、cdk2和GSK-3活性。包括公式1的化合物的制药组合物和方法用于治疗和预防包括异常细胞生长的疾病和症状，如癌症，神经退行性疾病和受多巴胺神经传递影响的疾病和症状。还描述了包括公式1的化合物的制药组合物和方法，用于治疗男性生育能力和精子活力；糖尿病；糖耐量受损；代谢综合征或X综合征；多囊卵巢综合征；脂肪生成和肥胖；肌肉生成和虚弱，例如与年龄相关的体能下降；急性肌肉萎缩，例如与烧伤、卧床休息、肢体固定或主要胸部、腹部和/或骨科手术相关的肌肉萎缩和/或虚脱；败血症；脱发、头发变薄和秃头；以及免疫缺陷。
• IMIDAZOLE DERIVATIVES
  申请人：Pfizer Products Inc.

  公开号：EP1305295A1

  公开（公告）日：2003-05-02
• US6756385B2
  申请人：——

  公开号：US6756385B2

  公开（公告）日：2004-06-29
• US7078529B2
  申请人：——

  公开号：US7078529B2

  公开（公告）日：2006-07-18
• [EN] IMIDAZOLE DERIVATIVES<br/>[FR] DERIVES D'IMIDAZOLE
  申请人：PFIZER PROD INC

  公开号：WO2002010141A1

  公开（公告）日：2002-02-07

  The invention provides compounds of formula (1), wherein R?1, R2, R3, and R4¿ are as defined, and their pharmaceutically acceptable salts. Compounds of formula (1) are indicated to have activity inhibiting cdk5, cdk2, and GSK-3. Pharmaceutical compositions and methods comprising compounds of formula (1) for treating and preventing diseases and conditions comprising abnormal cell growth, such as cancer, and neurodegenerative diseases and conditions and those affected by dopamine neurotransmission. Also described are pharmaceutical compositions and methods comprising compounds of formula (1) for treating male fertility and sperm motility; diabetes mellitus; impaired glucose tolerance; metabolic syndrome or syndrome X; polycystic ovary syndrome; adipogenesis and obesity; myogenesis and frailty, for example age-related decline in physical performance; acute sarcopenia, for example muscle atrophy and/or cachexia associated with burns, bed rest, limb immobilization, or major thoracic, abdominal, and/or orthopedic surgery; sepsis; hair loss, hair thinning, and balding; and immunodeficiency.