(2R)-1-(tert-butoxycarbonyl)-4-methylpiperazine-2-carboxylic acid | 363192-62-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R)-1-(tert-butoxycarbonyl)-4-methylpiperazine-2-carboxylic acid
• 英文别名: (2R)-4-methyl-1-[(2-methylpropan-2-yl)oxycarbonyl]piperazine-2-carboxylic acid
• CAS: 363192-62-5
• 化学式: C₁₁H₂₀N₂O₄
• 分子量: 244.291
• InChiKey: DEVGLXXPCHEYGJ-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  哌嗪 、 (2R)-1-(tert-butoxycarbonyl)-4-methylpiperazine-2-carboxylic acid 在 N-甲基吗啉 、 4-(4,6-二甲氧基三嗪-2-基)-4-甲基吗啉盐酸盐 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  The design and synthesis of novel, potent and orally bioavailable N-aryl piperazine-1-carboxamide CCR2 antagonists with very high hERG selectivity

  摘要：

  A novel N-aryl piperazine-1-carboxamide series of human CCR2 chemokine receptor antagonists was discovered. Early analogues were potent at CCR2 but also inhibited the hERG cardiac ion channel. Structural modifications which decreased lipophilicity and basicity resulted in the identification of a sub-series with an improved margin over hERG. The pharmacological and pharmacokinetic properties of the lead compound from this series, N-(3,4-dichlorophenyl)-4-[(2R)-4-isopropylpiperazine-2-carbonyl]piperazine-1-carboxamide, are described. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.118
• 作为产物：
  描述：

  (R)-1-BOC-2-甲酸哌嗪 、 碘甲烷 在 sodium carbonate 作用下， 以 乙醇 为溶剂， 生成 (2R)-1-(tert-butoxycarbonyl)-4-methylpiperazine-2-carboxylic acid
  参考文献：
  名称：

  The design and synthesis of novel, potent and orally bioavailable N-aryl piperazine-1-carboxamide CCR2 antagonists with very high hERG selectivity

  摘要：

  A novel N-aryl piperazine-1-carboxamide series of human CCR2 chemokine receptor antagonists was discovered. Early analogues were potent at CCR2 but also inhibited the hERG cardiac ion channel. Structural modifications which decreased lipophilicity and basicity resulted in the identification of a sub-series with an improved margin over hERG. The pharmacological and pharmacokinetic properties of the lead compound from this series, N-(3,4-dichlorophenyl)-4-[(2R)-4-isopropylpiperazine-2-carbonyl]piperazine-1-carboxamide, are described. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.118

文献信息

• Piperazine Compounds Useful as Antagonists of C-C Chemokines (Ccr2b and Ccr5) for the Treatment of Inflammatory Diseases
  申请人：Bower Justin Fairfield

  公开号：US20080287453A1

  公开（公告）日：2008-11-20

  A compound of formula (I) P—W—C(═X)-L-Q   (I) wherein P is an optionally substituted aryl or heteroaryl group; W is an optionally substituted 6 or 7-membered aliphatic ring comprising ring atoms Y 1 and Y 2 independently selected from Oxygen and Nitrogen, X is selected from Oxygen, Nitrogen and Sulphur; L is an optional C 1-4 linker; and Q is an optionally substituted 4-7 membered aliphatic ring: for use in the treatment of chemokine mediated diseases or disorders.

  化合物式为(I)P—W—C(═X)-L-Q  (I)的化合物，其中P是一种可选取的取代芳基或杂环芳基基团；W是一种可选取的6或7成员的脂环，包括环原子Y1和Y2，其独立地选自氧和氮，X选自氧、氮和硫；L是可选的C1-4连接基；Q是一种可选取的4-7成员的脂环；用于治疗趋化因子介导的疾病或疾病的化合物。
• US7943768B2
  申请人：——

  公开号：US7943768B2

  公开（公告）日：2011-05-17
• [EN] PIPERAZINE COMPOUNDS USEFUL AS ANTAGONISTS OF C-C CHEMOKINES (CCR2B AND CCR5) FOR THE TREATMENT OF INFLAMMATORY DISEASES<br/>[FR] PIPÉRAZINES POUVANT ÊTRE EMPLOYÉES EN TANT QU'ANTAGONISTES DE CHIMIOKINES C-C (CCR2B ET CCR5) DANS LE TRAITEMENT DE MALADIES INFLAMMATOIRES
  申请人：ASTRAZENECA AB

  公开号：WO2007071952A1

  公开（公告）日：2007-06-28

  [EN] A compound of formula (I) P - W - C(=X) - L - Q (I) wherein P is an optionally substituted aryl or heteroaryl group; W is an optionally substituted 6 or 7-membered aliphatic ring comprising ring atoms Y¹1 and Y² independently selected from Oxygen and Nitrogen, X is selected from Oxygen, Nitrogen and Sulphur; L is an optional C_1-4 linker; and Q is an optionally substituted 4-7membered aliphatic ring: for use in the treatment of chemokine mediated diseases or disorders.
  [FR] La présente invention a pour objet un composé de formule (I) P - W - C(=X) - L - Q (I) où P représente un groupement aryle ou hétéroaryle éventuellement substitué ; W représente un cycle aliphatique à 6 ou 7 chaînons éventuellement substitué comprenant des atomes de cycle Y¹1 ou Y² sélectionnés indépendamment parmi l'Oxygène et l'Azote, X est sélectionné parmi l'Oxygène, l'Azote et le Soufre ; L représente un groupement pontant optionnel en C₁-C₄ ; et Q représente un cycle aliphatique comportant entre 4 et 7 chaînons éventuellement substitué : pour emploi dans le traitement de maladies ou de troubles faisant intervenir les chimiokines.
• The design and synthesis of novel, potent and orally bioavailable N-aryl piperazine-1-carboxamide CCR2 antagonists with very high hERG selectivity
  作者：John G. Cumming、Justin F. Bower、David Waterson、Alan Faull、Philip J. Poyser、Paul Turner、Benjamin McDermott、Andrew D. Campbell、Julian Hudson、Michael James、Jon Winter、Christine Wood

  DOI：10.1016/j.bmcl.2012.04.118

  日期：2012.6

  A novel N-aryl piperazine-1-carboxamide series of human CCR2 chemokine receptor antagonists was discovered. Early analogues were potent at CCR2 but also inhibited the hERG cardiac ion channel. Structural modifications which decreased lipophilicity and basicity resulted in the identification of a sub-series with an improved margin over hERG. The pharmacological and pharmacokinetic properties of the lead compound from this series, N-(3,4-dichlorophenyl)-4-[(2R)-4-isopropylpiperazine-2-carbonyl]piperazine-1-carboxamide, are described. (C) 2012 Elsevier Ltd. All rights reserved.