tert-butyl 2-[(S)-1-[4-(ethoxycarbonyl)phenyl]ethyl]hydrazinecarboxylate | 870822-89-2

• 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: tert-butyl 2-[(S)-1-[4-(ethoxycarbonyl)phenyl]ethyl]hydrazinecarboxylate
• 英文别名: tert-butyl 2-{(1S)-1-[4-(ethoxycarbonyl)phenyl]ethyl}hydrazinecarboxylate；(S)-tert-butyl 2-{1-[4-(ethoxycarbonyl)phenyl]ethyl}hydrazinecarboxylate；(1S)-tert-butyl 2-{1-[4-(ethoxycarbonyl)phenyl]ethyl}hydrazinecarboxylate；tert-butyl 2-{1-[4-(ethoxycarbonyl)phenyl]ethyl}hydrazinecarboxylate；(S)-tert-butyl 2-(1-(4-(ethoxycarbonyl)phenyl)ethyl)hydrazinecarboxylate；ethyl 4-[(1S)-1-[2-[(2-methylpropan-2-yl)oxycarbonyl]hydrazinyl]ethyl]benzoate
• CAS: 870822-89-2
• 化学式: C₁₆H₂₄N₂O₄
• 分子量: 308.378
• InChiKey: UMABWHANJGIRER-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-[(S)-1-[4-(ethoxycarbonyl)phenyl]ethyl]hydrazinecarboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 4-(1-肼基乙基)苯甲酸乙酯
  参考文献：
  名称：

  Pyrazole derivatives, compositions containing such compounds and methods of use

  摘要：

  揭示了附有萘基团的吡唑类化合物。这些化合物可用于治疗2型糖尿病及相关疾病。还包括药物组合物和治疗方法。

  公开号：

  US20050272794A1
• 作为产物：
  描述：

  4-乙酰基苯甲酸乙酯 在 sodium cyanoborohydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 tert-butyl 2-[(S)-1-[4-(ethoxycarbonyl)phenyl]ethyl]hydrazinecarboxylate
  参考文献：
  名称：

  Discovery of a Novel Glucagon Receptor Antagonist N-[(4-{(1S)-1-[3-(3, 5-Dichlorophenyl)-5-(6-methoxynaphthalen-2-yl)-1H-pyrazol-1-yl]ethyl}phenyl)carbonyl]-β-alanine (MK-0893) for the Treatment of Type II Diabetes

  摘要：

  A potent, selective glucagon receptor antagonist 9m, N-[(4-{(1S)-1-[3-(3,5-dichlorophenyl) -5-(6-methoxynaphthalen-2-yl)-1H-pyrazol-1-yl]ethyl}phenyl)-carbonyl]-beta-alanine, was discovered by optimization of a previously identified lead. Compound 9m is a reversible and competitive antagonist with high binding affinity (IC50 of 6.6 nM) and functional cAMP activity (IC50 of 15.7 nM). It is selective for glucagon receptor relative to other family B GPCRs, showing IC50 values of 1020 nM for GIPR, 9200 nM for PAC1, and >10000 nM for GLP-1R, VPAC1, and VPAC2. Compound 9m blunted glucagon-induced glucose elevation in hGCGR mice and rhesus monkeys. It also lowered ambient glucose levels in both acute and chronic mouse models: in hGCGR ob/ob mice it reduced glucose (AUC 0-6 h) by 32% and 39% at 3 and 10 mpk single doses, respectively. In hGCGR mice on a high fat diet, compound 9m at 3, and 10 mpk po in feed lowered blood glucose levels by 89% and 94% at day 10, respectively, relative to the difference between the vehicle control and lean hGCGR mice. On the basis of its favorable biological and DMPK properties, compound 9m (MK-0893) was selected for further preclinical and clinical evaluations.

  DOI：

  10.1021/jm300579z

文献信息

• PYRAZOLE DERIVATIVES, COMPOSITIONS CONTAINING SUCH COMPOUNDS AND METHODS OF USE
  申请人：Parmee Emma R.

  公开号：US20090176854A1

  公开（公告）日：2009-07-09

  Pyrazoles having a naphthyl group attached are disclosed. The compounds are useful for treating type 2 diabetes and related conditions. Pharmaceutical compositions and methods of treatment are also included.

  本发明揭示了连接有萘基团的吡唑类化合物。这些化合物可用于治疗2型糖尿病及相关疾病。还包括制药组合物和治疗方法。
• [EN] SUBSTITUTED PYRAZOLES, COMPOSITIONS CONTAINING SUCH COMPOUNDS AND METHODS OF USE<br/>[FR] PYRAZOLES SUBSTITUES, COMPOSITIONS CONTENANT DE TELS COMPOSES ET LEURS METHODES D'UTILISATION
  申请人：MERCK & CO INC

  公开号：WO2006014618A3

  公开（公告）日：2006-10-19
• Catalytic Enantioselective Hydrogenation of <i>N</i>-Alkoxycarbonyl Hydrazones: A Practical Synthesis of Chiral Hydrazines
  作者：Naoki Yoshikawa、Lushi Tan、J. Christopher McWilliams、Deepa Ramasamy、Ruth Sheppard

  DOI：10.1021/ol902602c

  日期：2010.1.15

  An enantioselective hydrogenation of hydrazones catalyzed by Rh complexes (Rh-Josiphos or Rh-Taniaphos) has been developed. The protocol can be applied to hydrazones with three different protective groups (Boc, Cbz, and methoxycarbonyl), allowing for selective deprotection and further elaboration of the hydrazine products in the presence of other functional groups.
• US7598285B2
  申请人：——

  公开号：US7598285B2

  公开（公告）日：2009-10-06
• US7799818B2
  申请人：——

  公开号：US7799818B2

  公开（公告）日：2010-09-21