benzyl (1R,2R,4S)-4-(tert-butoxycarbonyl(methyl)amino)-2-(2,4-difluorophenyl)-cyclopentanecarboxylate | 934989-24-9

• 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: benzyl (1R,2R,4S)-4-(tert-butoxycarbonyl(methyl)amino)-2-(2,4-difluorophenyl)-cyclopentanecarboxylate
• 英文别名: benzyl (1R,2R,4S)-2-(2,4-difluorophenyl)-4-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]cyclopentane-1-carboxylate
• CAS: 934989-24-9
• 化学式: C₂₅H₂₉F₂NO₄
• 分子量: 445.506
• InChiKey: GSZXIUSFTPUGEB-SESVDKBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl (1R,2R,4S)-4-(tert-butoxycarbonyl(methyl)amino)-2-(2,4-difluorophenyl)-cyclopentanecarboxylate 在 5%-palladium/activated carbon 氢气 、 potassium carbonate 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 20.0~60.0 ℃ 、101.33 kPa 条件下， 反应 46.0h， 生成 [4-[2-(4-chloro-3-methyl-phenyl)-5-methyl-1,2,4-triazol-3-yl]-1-piperidyl]-[(1R,2R,4S)-2-(2,4-difluorophenyl)-4-(methyl(3,3,3-trifluoropropyl)amino)cyclopentyl]methanone trifluoroacetate
  参考文献：
  名称：

  [EN] NOVEL PROLYLCARBOXYPEPTIDASE INHIBITORS
  [FR] NOUVEAUX INHIBITEURS DE PROLYLCARBOXYPEPTIDASE

  摘要：

  结构公式I-1和I-2的化合物是脯氨酰羧肽酶（PrCP）的抑制剂。本发明的化合物可用于预防和治疗与PrCP的酶活性相关的状况，包括异常代谢，如肥胖、糖尿病、代谢综合征、与肥胖相关的疾病以及与糖尿病相关的疾病。

  公开号：

  WO2011156220A1
• 作为产物：
  描述：

  benzyl (1R,2R)-2-(2,4-difluorophenyl)-4-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]cyclopentane-1-carboxylate 生成 benzyl (1R,2R,4S)-4-(tert-butoxycarbonyl(methyl)amino)-2-(2,4-difluorophenyl)-cyclopentanecarboxylate 、 benzyl (1R,2R,4R)-2-(2,4-difluorophenyl)-4-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]cyclopentane-1-carboxylate
  参考文献：
  名称：

  WO2008/39418

  摘要：

  公开号：

文献信息

• Acylated piperidine derivatives as melanocortin-4 receptor modulators
  申请人：Bakshi Raman K.

  公开号：US20090253744A1

  公开（公告）日：2009-10-08

  Certain novel N-acylated spiropiperidine derivatives are ligands of the human melanocortin receptor(s) and, in particular, are selective ligands of the human melanocortin-4 receptor (MC-4R). They are therefore useful for the treatment, control, or prevention of diseases and disorders responsive to the modulation of MC-4R, such as obesity, diabetes, nicotine addiction, alcoholism, sexual dysfunction, including erectile dysfunction and female sexual dysfunction.

  某些新型N-酰化的螺环吡啶衍生物是人类黑色素细胞素受体的配体，特别是人类黑色素细胞素-4受体（MC-4R）的选择性配体。因此，它们可用于治疗、控制或预防对MC-4R调节敏感的疾病和障碍，如肥胖症、糖尿病、尼古丁成瘾、酗酒、性功能障碍，包括勃起功能障碍和女性性功能障碍。
• NOVEL PROLYLCARBOXYPEPTIDASE INHIBITORS
  申请人：Graham Thomas H.

  公开号：US20130143859A1

  公开（公告）日：2013-06-06

  Compounds of structural formulas I-1 and I-2 are inhibitors of prolylcarboxypeptidase (PrCP). The compounds of the present invention are useful for the prevention and treatment of conditions related to the enzymatic activity of PrCP such as abnormal metabolism, including obesity; diabetes; metabolic syndrome; obesity related disorders; and diabetes related disorders.

  结构式I-1和I-2的化合物是脯氨酰羧肽酶（PrCP）的抑制剂。本发明的化合物可用于预防和治疗与PrCP酶活性相关的疾病，如异常代谢，包括肥胖症，糖尿病，代谢综合征，肥胖相关疾病和糖尿病相关疾病。
• Discovery of highly potent and efficacious MC4R agonists with spiroindane N-Me-1,2,4-triazole privileged structures for the treatment of obesity
  作者：Shuwen He、Zhixiong Ye、Peter H. Dobbelaar、Raman K. Bakshi、Qingmei Hong、James P. Dellureficio、Iyassu K. Sebhat、Liangqin Guo、Jian Liu、Tianying Jian、Yingjie Lai、Christopher L. Franklin、Mikhail Reibarkh、Mark A. Holmes、David H. Weinberg、Tanya MacNeil、Rui Tang、Constantin Tamvakopoulos、Qianping Peng、Randy R. Miller、Ralph A. Stearns、Howard Y. Chen、Airu S. Chen、Alison M. Strack、Tung M. Fong、Matthew J. Wyvratt、Ravi P. Nargund

  DOI：10.1016/j.bmcl.2010.09.049

  日期：2010.11

  We report an SAR study of MC4R analogs containing spiroindane heterocyclic privileged structures. Compound 26 with N-Me-1,2,4-triazole moiety possesses exceptional potency at MC4R and potent anti-obesity efficacy in a mouse model. However, the efficacy is not completely mediated through MC4R. Additional SAR studies led to the discovery of compound 32, which is more potent at MC4R. Compound 32 demonstrates MC4R mediated anti-obesity efficacy in rodent models. (C) 2010 Elsevier Ltd. All rights reserved.
• ACYLATED SPIROPIPERIDINE DERIVATIVES AS MELANOCORTIN-4 RECEPTOR MODULATORS
  申请人：Bakshi Raman K.

  公开号：US20090325990A1

  公开（公告）日：2009-12-31

  Certain novel N-acylated spiropiperidine derivatives are ligands of the human melanocortin receptor(s) and, in particular, are selective ligands of the human melanocortin-4 receptor (MC-4R). They are therefore useful for the treatment, control, or prevention of diseases and disorders responsive to the modulation of MC-4R, such as obesity, diabetes, nicotine addiction, alcoholism, sexual dysfunction, including erectile dysfunction and female sexual dysfunction.
• US7652024B2
  申请人：——

  公开号：US7652024B2

  公开（公告）日：2010-01-26