3-(4-Chloro-benzylidene)-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester | 617714-57-5

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 托烷生物碱
• 英文名称: 3-(4-Chloro-benzylidene)-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester
• 英文别名: Tert-butyl 3-[(4-chlorophenyl)methylidene]-8-azabicyclo[3.2.1]octane-8-carboxylate
• CAS: 617714-57-5
• 化学式: C₁₉H₂₄ClNO₂
• 分子量: 333.858
• InChiKey: WMMXKWRRIMOWOF-UHFFFAOYSA-N

物化性质

• 沸点：
  445.9±38.0 °C(Predicted)
• 密度：
  1.188±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-Chloro-benzylidene)-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester 在 platinum(IV) oxide 氢气 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 3-(4-chloro-benzyl)-8-aza-bicyclo[3.2.1]octane
  参考文献：
  名称：

  Design and synthesis of novel CCR3 antagonists

  摘要：

  As part of our investigation into the development of potent CCR3 antagonists, a series of piperidine analogues was designed and prepared. Exploration of the piperidine core examined both the basicity and the location of a nitrogen, as well as conformational variants. The bicyclo-piperidine 24c was found to be the most potent inhibitor of CCR3 with an IC50 of 0.0082 muM in the binding assay and 0.0024 muM in the chemotaxis assay. (C) 2003 Published by Elsevier Ltd.

  DOI：

  10.1016/s0960-894x(03)00748-0
• 作为产物：
  描述：

  托品酮 在 1-氯乙基氯甲酸酯 、 potassium 2-methylbutan-2-olate 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 3-(4-Chloro-benzylidene)-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Design and synthesis of novel CCR3 antagonists

  摘要：

  As part of our investigation into the development of potent CCR3 antagonists, a series of piperidine analogues was designed and prepared. Exploration of the piperidine core examined both the basicity and the location of a nitrogen, as well as conformational variants. The bicyclo-piperidine 24c was found to be the most potent inhibitor of CCR3 with an IC50 of 0.0082 muM in the binding assay and 0.0024 muM in the chemotaxis assay. (C) 2003 Published by Elsevier Ltd.

  DOI：

  10.1016/s0960-894x(03)00748-0

文献信息

• Bridged bicyclic amine derivatives useful as CCR-3 receptor antagonists
  申请人：——

  公开号：US20040176416A1

  公开（公告）日：2004-09-09

  Compounds having the formula (I), Ar—(F)(E)-(CR 3 R 4 )—(CHR 5 ) m -(T)-(Q)-Ar 1 , are useful as CCR-3 receptor antagonists, wherein T is a bridged heterocyclyl group having one N atom and a bridge of one to two bridgehead carbon atoms; Ar and Ar 1 are aryl or heteroaryl; F is alkylene, alkenylene, or a bond; E is —C(═O)N(R 10 )—, —SO 2 N(R 10 )—, —N(R 11 )C(═O)N(R 10 O)—, —N(R 11 )SO 2 N(R 10 )—, —N(R 11 )C(═S)N(R 10 )—, —N(R 11 )C(═O)—, —N(R 11 )SO 2 —, —N(R 12 )C(═O)CH(R 13 )—, or CH(R 13 )C(═O)N(R 12 )—; Q is —C(═O)— or C 1-2 alkylene; and R 3 , R 4 , R 5 , R 9 , R 10 , R 11 , R 12 , and R 13 are defined as set forth in the specification.

  具有以下化学式的化合物(I)，Ar—(F)(E)-(CR3R4)—(CHR5)m-(T)-(Q)-Ar1，可用作CCR-3受体拮抗剂，其中T是具有一个N原子和一个到两个桥头碳原子的桥接杂环基团；Ar和Ar1是芳基或杂环芳基；F是烷基，烯烃基或键；E是—C(═O)N(R10)—，—SO2N(R10)—，—N(R11)C(═O)N(R10O)—，—N(R11)SO2N(R10)—，—N(R11)C(═S)N(R10)—，—N(R11)C(═O)—，—N(R11)SO2—，—N(R12)C(═O)CH(R13)—或CH(R13)C(═O)N(R12)—；Q是—C(═O)—或C1-2烷基；R3，R4，R5，R9，R10，R11，R12和R13如规范中所述定义。
• CCR-3 RECEPTOR ANTAGONISTS
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1599472A1

  公开（公告）日：2005-11-30
• US7081531B2
  申请人：——

  公开号：US7081531B2

  公开（公告）日：2006-07-25
• [EN] CCR-3 RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTES DU RECEPTEUR CCR-3
  申请人：HOFFMANN LA ROCHE

  公开号：WO2004076448A1

  公开（公告）日：2004-09-10

  The present invention relates to compounds of Formula (I), wherein: Ar, Arl, R3-R5, E, F, T, Q and m are as defined in the specification. The compounds are useful as CCR-3 Receptor antagonists, and therefore, may be used for the treatment of CCR-3 mediated diseases.