2-(3-Bromo-propyl)-5-methyl-benzoic acid methyl ester | 165803-55-4

• 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: 2-(3-Bromo-propyl)-5-methyl-benzoic acid methyl ester
• 英文别名: Methyl 2-(3-bromopropyl)-5-methylbenzoate
• CAS: 165803-55-4
• 化学式: C₁₂H₁₅BrO₂
• 分子量: 271.154
• InChiKey: YLCBLWSHBROBTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(3-Bromo-propyl)-5-methyl-benzoic acid methyl ester 在 sodium hydroxide 、 sodium tetrahydroborate 、 sodium hydride 、 sodium iodide 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-[3-(8-Hydroxy-7,8-dihydro-6H-imidazo[4,5-d][1,3]diazepin-3-yl)-propyl]-5-methyl-benzoic acid
  参考文献：
  名称：

  AMP Deaminase Inhibitors. 3. SAR of 3-(Carboxyarylalkyl)coformycin Aglycon Analogues

  摘要：

  N3-Substituted coformycin aglycon analogues with improved AMP deaminase (AMPDA) inhibitory potency are described. Replacement of the 5-carboxypentyl substituent in the lead AMPDA inhibitor 3-(5-carboxypentyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol (2) described in the previous article with various carboxyarylalkyl groups resulted in compounds with 10-100-fold improved AMPDA inhibitory potencies. The optimal N3 substituent had m-carboxyphenyl with a two-carbon alkyl tether. For example, 3-[2-(3-carboxy-5-ethylphenyl)-ethyl]-3,6,7,8-tetrahydroimidazo[4,5-d] [1,3]diazepin-8-ol (43g) inhibited human AMPDA with a K-i = 0.06 mu M. The compounds within the series also exhibited >1000-fold specificity for AMPDA relative to adenosine deaminase.

  DOI：

  10.1021/jm990448e
• 作为产物：
  描述：

  5-甲基水杨酸甲酯 在 palladium on activated charcoal bis-triphenylphosphine-palladium(II) chloride 、 四溴化碳 、 TEA 、 氢气 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， -78.0~60.0 ℃ 、206.85 kPa 条件下， 反应 1.5h， 生成 2-(3-Bromo-propyl)-5-methyl-benzoic acid methyl ester
  参考文献：
  名称：

  AMP Deaminase Inhibitors. 3. SAR of 3-(Carboxyarylalkyl)coformycin Aglycon Analogues

  摘要：

  N3-Substituted coformycin aglycon analogues with improved AMP deaminase (AMPDA) inhibitory potency are described. Replacement of the 5-carboxypentyl substituent in the lead AMPDA inhibitor 3-(5-carboxypentyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol (2) described in the previous article with various carboxyarylalkyl groups resulted in compounds with 10-100-fold improved AMPDA inhibitory potencies. The optimal N3 substituent had m-carboxyphenyl with a two-carbon alkyl tether. For example, 3-[2-(3-carboxy-5-ethylphenyl)-ethyl]-3,6,7,8-tetrahydroimidazo[4,5-d] [1,3]diazepin-8-ol (43g) inhibited human AMPDA with a K-i = 0.06 mu M. The compounds within the series also exhibited >1000-fold specificity for AMPDA relative to adenosine deaminase.

  DOI：

  10.1021/jm990448e

文献信息

• NOVEL INHIBITORS OF ADENOSINE MONOPHOSPHATE DEAMINASE
  申请人：GENSIA PHARMACEUTICALS, INC.

  公开号：EP0683781A1

  公开（公告）日：1995-11-29
• EP0683781A4
  申请人：——

  公开号：EP0683781A4

  公开（公告）日：1997-05-28
• US5731432A
  申请人：——

  公开号：US5731432A

  公开（公告）日：1998-03-24
• [EN] NOVEL INHIBITORS OF ADENOSINE MONOPHOSPHATE DEAMINASE<br/>[FR] NOUVEAUX INHIBITEURS DE L'ADENOSINE MONOPHOSPHATE DEAMINASE
  申请人：GENSIA, INC.

  公开号：WO1994018200A1

  公开（公告）日：1994-08-18

  (EN) Novel diazepine derivatives which selectively inhibit adenosine monophosphate deaminase and methods of preparing these compounds are provided. These compounds are useful in treating certain conditions $i(in vivo) which may be ameliorated by increased local concentrations of adenosine.(FR) Des dérivés nouveaux de diazépines inhibent sélectivement l'adénosine monophosphate déaminase et des procédés permettent de préparer ces composés qui sont utiles pour traiter $i(in vivo) certains troubles qu'on peut atténuer grâce à des concentrations locales accrues d'adénosine.
• AMP Deaminase Inhibitors. 3. SAR of 3-(Carboxyarylalkyl)coformycin Aglycon Analogues
  作者：Srinivas Rao Kasibhatla、Brett C. Bookser、Gary Probst、James R. Appleman、Mark D. Erion

  DOI：10.1021/jm990448e

  日期：2000.4.1

  N3-Substituted coformycin aglycon analogues with improved AMP deaminase (AMPDA) inhibitory potency are described. Replacement of the 5-carboxypentyl substituent in the lead AMPDA inhibitor 3-(5-carboxypentyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol (2) described in the previous article with various carboxyarylalkyl groups resulted in compounds with 10-100-fold improved AMPDA inhibitory potencies. The optimal N3 substituent had m-carboxyphenyl with a two-carbon alkyl tether. For example, 3-[2-(3-carboxy-5-ethylphenyl)-ethyl]-3,6,7,8-tetrahydroimidazo[4,5-d] [1,3]diazepin-8-ol (43g) inhibited human AMPDA with a K-i = 0.06 mu M. The compounds within the series also exhibited >1000-fold specificity for AMPDA relative to adenosine deaminase.