(3-bromo-1-(R)-methyl-2-oxopropyl)carbamic acid benzyl ester | 852248-32-9

• 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: (3-bromo-1-(R)-methyl-2-oxopropyl)carbamic acid benzyl ester
• 英文别名: (R)-benzyl 4-bromo-3-oxobutan-2-yl carbamate；benzyl N-[(2R)-4-bromo-3-oxobutan-2-yl]carbamate
• CAS: 852248-32-9
• 化学式: C₁₂H₁₄BrNO₃
• 分子量: 300.152
• InChiKey: YTCSMFTYZYCVFP-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3-bromo-1-(R)-methyl-2-oxopropyl)carbamic acid benzyl ester 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (R)-benzyl 1-(5-amino-1H-pyrazol-3-yl)ethylcarbamate
  参考文献：
  名称：

  Synthesis of N-Urethane Protected α-Aminoalkyl-α′-cyanomethyl Ketones; Application to the Synthesis of 3-Substituted 5-Amino-1H-pyrazole Tethered Peptidomimetics

  摘要：

  The preparation of N-protected amino/peptide alpha-cyanomethyl ketones through cyanation of the corresponding alpha-bromomethyl ketones is described. The utility of the resulting acyanomethyl ketones in the synthesis of 3-substituted-5-amino-1H-pyrazoles has also been demonstrated. In both steps a wide range of N-protected amino/peptide acids has been employed and the products are obtained in good yield. The enantiomeric purity of both the alpha-cyanomethyl ketones and pyrazoles were confirmed by chiral HPLC analysis of the corresponding Z-protected D-and L-Ala-OH as model substrates. The synthesis of peptide pyrazolecarbox-amides is also delineated.

  DOI：

  10.1055/s-0032-1316586
• 作为产物：
  描述：

  (3-diazo-1-(R)-methyl-2-oxopropyl)carbamic acid benzyl ester 在 氢溴酸 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 (3-bromo-1-(R)-methyl-2-oxopropyl)carbamic acid benzyl ester
  参考文献：
  名称：

  Synthesis of N-Urethane Protected α-Aminoalkyl-α′-cyanomethyl Ketones; Application to the Synthesis of 3-Substituted 5-Amino-1H-pyrazole Tethered Peptidomimetics

  摘要：

  The preparation of N-protected amino/peptide alpha-cyanomethyl ketones through cyanation of the corresponding alpha-bromomethyl ketones is described. The utility of the resulting acyanomethyl ketones in the synthesis of 3-substituted-5-amino-1H-pyrazoles has also been demonstrated. In both steps a wide range of N-protected amino/peptide acids has been employed and the products are obtained in good yield. The enantiomeric purity of both the alpha-cyanomethyl ketones and pyrazoles were confirmed by chiral HPLC analysis of the corresponding Z-protected D-and L-Ala-OH as model substrates. The synthesis of peptide pyrazolecarbox-amides is also delineated.

  DOI：

  10.1055/s-0032-1316586

文献信息

• Aryl nitrile compounds and compositions and their uses in treating inflammatory and related disorders
  申请人：Bergeron Philippe

  公开号：US20070015773A1

  公开（公告）日：2007-01-18

  Compounds, compositions and methods that are useful in the treatment of inflammatory and immune conditions and diseases are provided herein. In particular, the invention provides aryl nitrile compounds which modulate the expression and/or function of a chemokine receptor. The subject methods are useful for the treatment of inflammatory and immunoregulatory disorders and diseases, such as multiple sclerosis, rheumatoid arthritis, type I diabetes, asthma, psoriasis and inflammatory bowel disease.

  本文提供了在治疗炎症和免疫相关疾病中有用的化合物、组合物和方法。具体来说，本发明提供了可以调节趋化因子受体的表达和/或功能的芳基腈化合物。这些方法适用于治疗炎症和免疫调节性疾病，例如多发性硬化症、类风湿性关节炎、1型糖尿病、哮喘、牛皮癣和炎症性肠病。
• WO2007/2701
  申请人：——

  公开号：——

  公开（公告）日：——
• Optimization of the heterocyclic core of the quinazolinone-derived CXCR3 antagonists
  作者：An-Rong Li、Michael G. Johnson、Jiwen Liu、Xiaoqi Chen、Xiaohui Du、Jeffrey T. Mihalic、Jeffrey Deignan、Darin J. Gustin、Jason Duquette、Zice Fu、Liusheng Zhu、Andrew P. Marcus、Phillipe Bergeron、Lawrence R. McGee、Jay Danao、Bryan Lemon、Teresa Carabeo、Timothy Sullivan、Ji Ma、Liang Tang、George Tonn、Tassie L. Collins、Julio C. Medina

  DOI：10.1016/j.bmcl.2007.11.060

  日期：2008.1

  A series of six-six and six-five fused heterocyclic CXCR3 antagonists has been synthesized and their activities evaluated in an [I-125]-IP-10 displacement assay and an ITAC mediated in vitro cell migration assay. The pharmacokinetic properties of several top compounds have also been studied. This effort led to the discovery of compounds with increased potency and improved pharmacokinetic properties that could serve as useful tools to study the role of the CXCR3 receptor in vivo. (c) 2007 Elsevier Ltd. All rights reserved.
• Chiral imidazole derivatives synthesis from enantiopure N-protected α-amino acids
  作者：Filip Bureš、Jiří Kulhánek

  DOI：10.1016/j.tetasy.2005.01.049

  日期：2005.4

  A route to the preparation of enantiopure ligands based on a 2-phenylimidazol ring is described. The stereogenic centre is placed into the chain bonded to the fourth carbon of the imidazole ring. The synthesis starts from inexpensive and readily available N-protected alpha-amino acids, as the source of chirality, which are converted into appropriate alpha-diazoketones and, consequently, into alpha-bromoketones. These alpha-bromoketones are good precursors for reactions with amidines to provide the imidazole ring. The deprotection into the final products was carried out using hydrogen. (c) 2005 Elsevier Ltd. All rights reserved.
• Imidazo-pyrazine derivatives as potent CXCR3 antagonists
  作者：Xiaohui Du、Darin J. Gustin、Xiaoqi Chen、Jason Duquette、Lawrence R. McGee、Zhulun Wang、Karen Ebsworth、Kirk Henne、Bryan Lemon、Ji Ma、Shichang Miao、Emmanuel Sabalan、Timothy J. Sullivan、George Tonn、Tassie L. Collins、Julio C. Medina

  DOI：10.1016/j.bmcl.2009.07.021

  日期：2009.9

  A general way of improving the potency of CXCR3 antagonists with fused hetero-bicyclic cores was identified. Optimization efforts led to the discovery of a series of imidazo-pyrazine derivatives with improved pharmacokinetic properties in addition to increased potency. The efficacy of the lead compound 21 is evaluated in a mouse lung inflammation model. Published by Elsevier Ltd.