methyl 1-(2-bromoethyl)-3-naphthoate | 331281-96-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 1-(2-bromoethyl)-3-naphthoate
• 英文别名: Methyl 4-(2'-Bromoethyl)-2-naphthoate；methyl 4-(2-bromoethyl)naphthalene-2-carboxylate
• CAS: 331281-96-0
• 化学式: C₁₄H₁₃BrO₂
• 分子量: 293.16
• InChiKey: ZJDYSDLZUSGSBS-UHFFFAOYSA-N

物化性质

• 沸点：
  398.3±25.0 °C(Predicted)
• 密度：
  1.413±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  methyl 1-(2-bromoethyl)-3-naphthoate 在 sodium tetrahydroborate 、 sodium hydride 、 sodium iodide 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-[2-(8-Hydroxy-7,8-dihydro-6H-imidazo[4,5-d][1,3]diazepin-3-yl)-ethyl]-naphthalene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  AMP Deaminase Inhibitors. 5. Design, Synthesis, and SAR of a Highly Potent Inhibitor Series

  摘要：

  A highly potent AMP deaminase (AMPDA) inhibitor series was discovered by replacing the N3 substitutents of the two lead AMPDA inhibitor series with a conformationally restricted group. The most potent compound, 3-[2-(3-carboxy-4-bromo-5,6,7,8-tetrahydroaphthyl)ethyl]-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol (24b), represents a 10- to 250-fold enhancement in AMPDA inhibitory potency without loss in the enzyme specificity. The potency of the inhibitor 24b (AMPDA K-i = 0.002 muM) is 10(5)-fold lower than the K-m for the substrate AMP. It represents the most potent nonnucleotide AMPDA inhibitor known.

  DOI：

  10.1021/jm000355t
• 作为产物：
  描述：

  1-溴-3-萘酸甲酯 在 9-borabicyclo[3.3.1]nonane dimer 、 四(三苯基膦)钯 、 四溴化碳 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.5h， 生成 methyl 1-(2-bromoethyl)-3-naphthoate
  参考文献：
  名称：

  AMP Deaminase Inhibitors. 5. Design, Synthesis, and SAR of a Highly Potent Inhibitor Series

  摘要：

  A highly potent AMP deaminase (AMPDA) inhibitor series was discovered by replacing the N3 substitutents of the two lead AMPDA inhibitor series with a conformationally restricted group. The most potent compound, 3-[2-(3-carboxy-4-bromo-5,6,7,8-tetrahydroaphthyl)ethyl]-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol (24b), represents a 10- to 250-fold enhancement in AMPDA inhibitory potency without loss in the enzyme specificity. The potency of the inhibitor 24b (AMPDA K-i = 0.002 muM) is 10(5)-fold lower than the K-m for the substrate AMP. It represents the most potent nonnucleotide AMPDA inhibitor known.

  DOI：

  10.1021/jm000355t

文献信息

• Inhibitors of adenosine monophosphate deaminase
  申请人：Gensia Sicor Inc.

  公开号：US05731432A1

  公开（公告）日：1998-03-24

  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 in vivo which may be ameliorated by increased local concentrations of adenosine.

  提供了一种新型的二氯硝唑啶衍生物，可以选择性地抑制腺苷单磷酸脱氨酶，并提供了制备这些化合物的方法。这些化合物在体内治疗某些病症方面很有用，这些病症可能通过增加腺苷的局部浓度来改善。
• 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.