2-(3-溴丙基)苯甲酸甲酯 | 165803-48-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(3-溴丙基)苯甲酸甲酯
• 英文名称: methyl 2-(3-bromopropyl) benzoate
• 英文别名: Methyl 2-(3-bromopropyl)benzoate
• CAS: 165803-48-5
• 化学式: C₁₁H₁₃BrO₂
• 分子量: 257.127
• InChiKey: TWOSSTVSFCNWQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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-溴丙基)苯甲酸甲酯 在 sodium tetrahydroborate 、 sodium hydride 、 sodium iodide 作用下， 以 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]-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
• 作为产物：
  描述：

  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-溴丙基)苯甲酸甲酯
  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

• Functionalized esters as bis-electrophiles in a silicon-induced domino synthesis of annulated carbocycles
  作者：Florian Genrich、Guido Harms、Ernst Schaumann、Mimoza Gjikaj、Gunadi Adiwidjaja

  DOI：10.1016/j.tet.2009.01.119

  日期：2009.7

  The reaction of silyl-substituted carbanion 1b with arene-1,2-dicarboxylates 6, 15 yields indenone derivatives 11, 16 in a domino process involving silyl C→O migration and elimination. However, in a competing pathway, the initial addition of 1b leads to lactone formation (8, 17). Substrates 26, 38 containing an ester group and a bromine substituent react with 1b under substitution of the halogen not

  甲硅烷基取代的碳负离子反应1B与芳烃- 1,2-二羧酸酯6，15个产量茚酮衍生物11，16在涉及甲硅烷→O;迁移和消除℃的多米诺过程。然而，在竞争途径中，初始加入1B导致内酯的形成（8，17）。基底26，38含酯基团和取代基溴与反应1b的下不允许甲硅烷迁移卤素取代。但是用TBAF进行的去甲硅烷基化反应会产生反应性碳负离子，从而提供苯并环化的环烷酮29，40。
• Identification of Small Molecules Blocking the Pseudomonas aeruginosa Type III Secretion System Protein PcrV
  作者：Charlotta Sundin、Michael Saleeb、Sara Spjut、Liena Qin、Mikael Elofsson

  DOI：10.3390/biom11010055

  日期：——

  Pseudomonas aeruginosa is an opportunistic bacterial pathogen that employs its type III secretion system (T3SS) during the acute phase of infection to translocate cytotoxins into the host cell cytoplasm to evade the immune system. The PcrV protein is located at the tip of the T3SS, facilitates the integration of pore-forming proteins into the eukaryotic cell membrane, and is required for translocation of cytotoxins into the host cell. In this study, we used surface plasmon resonance screening to identify small molecule binders of PcrV. A follow-up structure-activity relationship analysis resulted in PcrV binders that protect macrophages in a P. aeruginosa cell-based infection assay. Treatment of P. aeruginosa infections is challenging due to acquired, intrinsic, and adaptive resistance in addition to a broad arsenal of virulence systems such as the T3SS. Virulence blocking molecules targeting PcrV constitute valuable starting points for development of next generation antibacterials to treat infections caused by P. aeruginosa.

  铜绿假单胞菌是一种机会性细菌病原体，它在感染的急性阶段利用其III型分泌系统（T3SS）将细胞毒素转运到宿主细胞胞质中，以逃避免疫系统。PcrV蛋白位于T3SS的顶端，促进孔形成蛋白与真核细胞膜的整合，并且需要将细胞毒素转运到宿主细胞中。在这项研究中，我们使用表面等离子共振筛选识别PcrV的小分子结合物。随后进行的结构-活性关系分析得出了能在基于P. aeruginosa细胞的感染实验中保护巨噬细胞的PcrV结合物。治疗P. aeruginosa感染具有挑战性，因为除了广泛的毒力系统（如T3SS）外，还存在获得性、固有性和适应性抗性。针对PcrV的毒力阻断分子为开发下一代抗菌剂治疗由铜绿假单胞菌引起的感染提供了宝贵的起点。
• Assessment of dopamine D1 receptor affinity and efficacy of three tetracyclic conformationally-restricted analogs of SKF38393
  作者：Alia H. Clark、John D. McCorvy、Val J. Watts、David E. Nichols

  DOI：10.1016/j.bmc.2011.07.057

  日期：2011.9

  To assess the effect of conformational mobility on receptor activity, the beta-phenyl substituent of dopamine D-1 agonist ligands of the phenylbenzazepine class, (+/-)-6,6a, 7,8,9,13b-hexahydro-5H-benzo[d] naphtho[ 2,1-b] azepine-11,12-diol (8), and its oxygen and sulfur bioisosteres 9 and 10, respectively, were synthesized as conformationally-restricted analogs of SKF38393, a dopamine D-1-selective partial agonist. Compounds trans-8b, 9, and 10 showed binding affinity comparable to that of SKF38393, but functionally, they displayed only very weak agonist activity. These results suggest that the conformationally-restricted structure of the analogs cannot adopt a binding orientation that is necessary for agonist activity. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis and antifungal activity of 7-methyl-7-hydroxy-2,3-benzo[c]octa-1,6-olide
  作者：Jin Zhao、Hong-Bo Dong、Ming-Yan Yang、Juan Du、Jia-Zheng Jiang、Ming-An Wang

  DOI：10.1080/10286020.2013.879121

  日期：2014.3.4

  The racemic 7-methyl-7-hydroxy-2,3-benzo[c]octa-1,6-olide, the analog of natural product (6R)-3,7-dimethyl-7-hydroxy-2-octen-1,6-olide, was totally synthesized using easily available (E)-2-(2-carboxyvinyl)benzoic acid as a raw material in nine-step reactions including three key steps of Wittig reaction, epoxidation, and cyclization, with an overall yield of 10.3%. The bioassay results showed that (+/-)-2 exhibited stronger antifungal activity than the natural product (+/-)-1 and (R)-1 against Alternaria solani with an EC50 value of 27.36g/ml.
• NOVEL INHIBITORS OF ADENOSINE MONOPHOSPHATE DEAMINASE
  申请人：GENSIA PHARMACEUTICALS, INC.

  公开号：EP0683781A1

  公开（公告）日：1995-11-29