3-(Bromomethyl)-4-chlorobenzoic acid | 1187237-82-6

• 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-(Bromomethyl)-4-chlorobenzoic acid
• CAS: 1187237-82-6
• 化学式: C₈H₆BrClO₂
• mdl: MFCD17676542
• 分子量: 249.491
• InChiKey: JUJAOSCAZDKRGN-UHFFFAOYSA-N

物化性质

• 沸点：
  366.4±32.0 °C(Predicted)
• 密度：
  1.739±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(Bromomethyl)-4-chlorobenzoic acid 、 (7S)-7-氨基-1,2,3-三甲氧基-10-甲硫基-6,7-二氢-5H-苯并[g]庚搭烯-9-酮 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-3-(bromomethyl)-4-chloro-N-(1,2,3-trimethoxy-10-(methylthio)-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl)benzamide
  参考文献：
  名称：

  Design, synthesis and identification of novel colchicine-derived immunosuppressant

  摘要：

  Synthesis and biological evaluation of various colchicine analogues through the mixed-lymphocyte reaction (MLR), lymphoproliferation, and inhibitory effects on the inflammatory genes are described. In addition, a new series of immunosuppressive agents developed on the structural basis of colchicine, as well as their structure-activity relationships is reported. The most potent analogue 20a exhibited an excellent immunosuppressive activity on in vivo skin-allograft model, which is comparable to that of cyclosporin A. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.05.054
• 作为产物：
  描述：

  3-溴甲基-4-氯苯甲酸甲酯 在 水 作用下， 以 甲醇 为溶剂， 生成 3-(Bromomethyl)-4-chlorobenzoic acid 、 4-chloro-3-(hydroxymethyl)benzoic acid
  参考文献：
  名称：

  Design, synthesis and identification of novel colchicine-derived immunosuppressant

  摘要：

  Synthesis and biological evaluation of various colchicine analogues through the mixed-lymphocyte reaction (MLR), lymphoproliferation, and inhibitory effects on the inflammatory genes are described. In addition, a new series of immunosuppressive agents developed on the structural basis of colchicine, as well as their structure-activity relationships is reported. The most potent analogue 20a exhibited an excellent immunosuppressive activity on in vivo skin-allograft model, which is comparable to that of cyclosporin A. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.05.054

文献信息

• DERIVES DE 5-ALKYLOXY-INDOLIN-2-ONE, LEUR PREPARATION ET LEURS APPLICATIONS EN THERAPEUTIQUE COMME LIGANDS SELECTIVES DES RECEPTEURS V2 DE LA VASOPRESSINE
  申请人：Sanofi-Aventis

  公开号：EP2097374A2

  公开（公告）日：2009-09-09
• [EN] 5-ALKYLOXY-INDOLIN-2-ONE DERIVATIVES, PREPARATION THEREOF AND APPLICATION THEREOF IN THERAPY<br/>[FR] DERIVES DE 5-ALKYLOXY-INDOLIN-2-ONE, LEUR PREPARATION ET LEURS APPLICATIONS EN THERAPEUTIQUE
  申请人：SANOFI AVENTIS

  公开号：WO2008087278A2

  公开（公告）日：2008-07-24

  [EN] The invention relates to compounds of the formula (I) in which: R₀ is (C₁-C₄)alkyl, mono or polyfluoro-(C₁C₄)alkyl, cyclopropyl or -CH2- cyclopropyl, (C₂-C₄)alkenyl or (C₂-C₄)alkynyl; R₁ is H, (C₁-C₅)alkyl, mono or polyfluoro-(C₁C₅)alkyl, hydroxy-(C₂-C₅)alkyl, -(CH₂)m-(C₃-C₅)cycloalkyl; Z₁ is H or halogen, (C₁C₄)alkyl, mono or polyfluoro-(C-₁-C₄)alkyl, (C₁- C₄)alkoxy, mono or PoIy[IuOrO-(C₁-C₄)Alkoxy, cyclopropyl or -CH₂-yclopropyle, optionally substituted; Z₂ is a halogen atom or a T₁W group, in which T₁ is a -(CH₂)_n- group, and W is one or more of H, (C₁- C₄)alkyl, mono or polyfluoro-(C-₁-C₄)alkyl or cyclopropyl optionally substituted, or W is -C(O)OR₁₉, or W is -C(O)NR₆R₇, or W is a -NR₈C(O)R₉ group, or W is -NR₁₀R₁₁, or W is a -OR₁₂ group; R₄ is (CrC4)alkyl, mono or polyfluoro-(C₁C₄)alkyl, OH, (C₁- C₄)alkoxy, (C2-C4) alkenyl, nitro, COORCl, benzyloxy, or R₄ is - C(O)NR₁₃R₁₄, or R₄ is -NR₁₅R₁₆, or R₄ is -NR₁₇C(O)R₁₈; R₃ and R₅ are H or halogen, (CrC4)alkyl, mono or polyfluoro-(CrC4)alkyl, (C₁- C₄)alkoxy or mono or polyfluoro-(C₁C₄)alkoxy; m = 0, 1 or 2; n = 0 or 1; said compounds being in their base, hydrate or solvate state, in the form of cis/trans isomers, or mixtures thereof. The invention also relates to a method for the preparation of the compounds of the formula (I) and to the use thereof in therapy.
  [FR] La présente invention a pour objet des composés de formule (I) dans laquelle R₀ représente un (C₁-C₄)alkyle, mono ou polyfluoro-(C₁C₄)alkyle, cyclopropyle ou -CH2- cyclopropyle, (C₂-C₄)alcényle ou (C₂-C₄)alcynyle; R₁ représente H, (C₁-C₅)alkyle, mono ou polyfluoro-(C₁C₅)alkyle, hydroxy-(C₂-C₅)alkyle, -(CH₂)m-(C₃-C₅)cycloalkyle; Z₁ représente H ou halogène, (C₁C₄)alkyle, mono ou polyfluoro-(C-₁-C₄)alkyle, (C₁- C₄)alcoxy, mono ou PoIy[IuOrO-(C₁-C₄)Alcoxy, cyclopropyle ou -CH₂-yclopropyle, éventuellement substitués; Z₂ représente un atome d'halogène ou un groupe T₁W, dans lequel T₁ représente un groupe -(CH₂)_n- et W représente un ou plusieurs H, (C₁- C₄)alkyle, mono ou polyfluoro-(C-₁-C₄)alkyle ou cyclopropyle éventuellement substitué, ou bien W représente -C(O)OR_19, ou bien W représente -C(O)NR₆R₇, ou bien W représente un groupe -NR₈C(O)R₉, ou bien W représente -NR₁₀R₁₁, ou bien W représente un groupe -OR₁₂; R₄ représente (CrC4)alkyle, mono ou polyfluoro-(C₁C₄)alkyle, OH, (C₁- C₄)alcoxy, (C2-C4) alcényle, nitro, COORCl un benzyloxy, ou bien R₄ représente - C(O)NR₁₃R₁₄, ou bien R₄ représente -NR₁₅R₁₆, ou bien R₄ représente -NR₁₇C(O)R₁₈; R₃ et R₅ représentent H ou halogène, (CrC4)alkyle, mono ou polyfluoro-(CrC4)alkyle, (C₁- C₄)alcoxy ou mono ou polyfluoro-(C₁C₄)alcoxy; m = O, 1 ou 2; n = O ou 1; à l'état de base, d'hydrate ou de solvat, sous forme d'isomères cis/trans ou de leurs mélanges. L'invention concerne également le procédé de préparation ainsi que les utilisations en thérapeutique des composés de formule (I).
• Design, synthesis and identification of novel colchicine-derived immunosuppressant
  作者：Dong-Jo Chang、Eun-Young Yoon、Geon-Bong Lee、Soon-Ok Kim、Wan-Joo Kim、Young-Myeong Kim、Jong-Wha Jung、Hongchan An、Young-Ger Suh

  DOI：10.1016/j.bmcl.2009.05.054

  日期：2009.8

  Synthesis and biological evaluation of various colchicine analogues through the mixed-lymphocyte reaction (MLR), lymphoproliferation, and inhibitory effects on the inflammatory genes are described. In addition, a new series of immunosuppressive agents developed on the structural basis of colchicine, as well as their structure-activity relationships is reported. The most potent analogue 20a exhibited an excellent immunosuppressive activity on in vivo skin-allograft model, which is comparable to that of cyclosporin A. (C) 2009 Elsevier Ltd. All rights reserved.