1-phenylcyclopropane carbohydrazide | 851764-93-7

• 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: 1-phenylcyclopropane carbohydrazide
• 英文别名: 1-Phenylcyclopropane-1-carbohydrazide
• CAS: 851764-93-7
• 化学式: C₁₀H₁₂N₂O
• mdl: MFCD11643328
• 分子量: 176.218
• InChiKey: YVJWOLJETZHTGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-phenylcyclopropane carbohydrazide 在 四溴化碳 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 、 三苯基膦 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 cyclohexyl (S)-4-([1,1'-biphenyl]-4-carboxamido)-4-(5-(1-phenylcyclopropyl)-1,3,4-oxadiazol-2-yl)butanoate
  参考文献：
  名称：

  Structure–activity study on a series of α-glutamic acid scaffold based compounds as new ADAMTS inhibitors

  摘要：

  A series of alpha-glutamic acid scaffold based 4-(benzamido)-4-(1,3,4-oxadiazol-2-yl) butanoic acids were designed and synthesized as new ADAMTS inhibitors. The compounds dose-dependently inhibited the enzymatic activities of ADAMTS-4 and ADAMTS-5. One of the most active compound 2h potently inhibited ADAMTS-4 and ADAMTS-5 with IC(50) values of 1.2 and 0.8 mu M, respectively. These inhibitors may serve as new lead compounds for further development of therapeutics to treat osteoarthritis. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.009

文献信息

• Compounds, compositions and methods
  申请人：Denali Therapeutics Inc.

  公开号：US10131676B2

  公开（公告）日：2018-11-20

  The present disclosure relates generally to compounds and compositions, and their use as kinase inhibitors.

  本公开总体上涉及化合物和组合物，以及它们作为激酶抑制剂的用途。
• Biarylpyrazolyl Oxadiazole as Potent, Selective, Orally Bioavailable Cannabinoid-1 Receptor Antagonists for the Treatment of Obesity
  作者：Suk Ho Lee、Hee Jeong Seo、Sung-Han Lee、Myung Eun Jung、Ji-Hyun Park、Hyun-Ju Park、Jakyung Yoo、Hoseop Yun、Jooran Na、Suk Youn Kang、Kwang-Seop Song、Min-ah Kim、Chong-Hwan Chang、Jeongmin Kim、Jinhwa Lee

  DOI：10.1021/jm800843r

  日期：2008.11.27

  Since the CB1 cannabinoid receptor antagonist 1 (SR141716, rimonabant) was previously reported to modulate food intake, CB1 antagonism has been considered as a new therapeutic target for the treatment of obesity. In the present study, biarylpyrazole analogues based on a pyrazole core coupled with 1,3,4-oxadiazole were synthesized and tested for CB1 receptor binding affinity. Thorough SAR studies to optimize pyrazole substituents as well as 1,3,4-oxadiazole ring led to several novel CB1 antagonists with IC50 similar to 1 nM for the CB1 receptor binding. Among these analogues, we identified 2-(4-((1H-1,2,4-triazol-1-yl)methyl)-5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl)-5-(1-(trifluoromethyl)cyclopropyl)-1,3,4-oxa- diazole 43c as a promising precandidate for the development as an antiobesity agent.
• Diarylimidazolyl oxadiazole and thiadiazole derivatives as cannabinoid CB1 receptor antagonists
  作者：Jong Yup Kim、Hee Jeong Seo、Sung-Han Lee、Myung Eun Jung、Kwangwoo Ahn、Jeongmin Kim、Jinhwa Lee

  DOI：10.1016/j.bmcl.2008.10.130

  日期：2009.1

  Since the CB1 receptor antagonist SR141716 (rimonabant) was reported to modulate food intake, CB1 antagonism has been considered as a new therapeutic target in the treatment of obesity. Several series of derivatives based on diarylimidazolyl oxadiazole and thiadiazole scaffolds were synthesized and tested for CB1 receptor binding affinity. SAR studies directed toward the optimization of imidazole scaffolds resulted in the discovery of 10s which showed highest potency for CB1 receptor binding affinity (IC50 = 1.91 nM) prepared to date. (C) 2008 Elsevier Ltd. All rights reserved.
• Phenylcyclobutyl triazoles as selective inhibitors of 11β-hydroxysteroid dehydrogenase type I
  作者：Yuping Zhu、Steven H. Olson、Donald Graham、Gool Patel、Anne Hermanowski-Vosatka、Steven Mundt、Kashmira Shah、Marty Springer、Rolf Thieringer、Samuel Wright、Jianying Xiao、Hratch Zokian、Jasminka Dragovic、James M. Balkovec

  DOI：10.1016/j.bmcl.2008.04.014

  日期：2008.6

  3-(Phenylcyclobutyl)-1,2,4-triazoles were identified as selective inhibitors of 11 beta-hydroxysteroid dehydrogenase type 1 (11 beta-HSD1). These were active both in vitro and in an in vivo mouse pharmacodynamic (PD) model. Fluorine substitution of the cyclobutane ring improved the pharmacokinetic profile significantly. The synthesis and structure-activity relationships are presented. (c) 2008 Elsevier Ltd. All rights reserved.
• [EN] TRIAZOLE COMPOUNDS AND USES RELATED THERETO<br/>[FR] COMPOSES TRIAZOLE ET UTILISATIONS ASSOCIEES
  申请人：AMGEN SF LLC

  公开号：WO2005044192A3

  公开（公告）日：2005-09-09