3-溴甲基苯甲酸苯酯 | 129250-89-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 中文名称: 3-溴甲基苯甲酸苯酯
• 英文名称: α-bromo-3-methylphenyl benzoate
• 英文别名: 3-(bromomethyl)phenyl benzoate；3-(benzoyloxy)benzyl bromide；3-Benzoyloxybenzyl bromide；[3-(bromomethyl)phenyl] benzoate
• CAS: 129250-89-1
• 化学式: C₁₄H₁₁BrO₂
• 分子量: 291.144
• InChiKey: VJGOZOYBJUTQKK-UHFFFAOYSA-N

物化性质

• 沸点：
  389.4±25.0 °C(Predicted)
• 密度：
  1.438±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  3-溴甲基苯甲酸苯酯 在 hydroxide 作用下， 生成 1-(3-{12-[3-(6-Amino-purin-9-ylmethyl)-phenoxy]-dodecyloxy}-benzyl)-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Preparation of an intramolecularadenine-thymine base pair

  摘要：

  DOI：

  10.1016/s0040-4039(00)88758-4
• 作为产物：
  描述：

  间甲苯基苯甲酸酯 在 过氧化苯甲酰 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 、 水 为溶剂， 生成 3-溴甲基苯甲酸苯酯
  参考文献：
  名称：

  Antiosteoporotic imidazo[4,5-c]pyridines

  摘要：

  这项发明涉及2-取代咪唑[4,5-c]吡啶，以及它们的制备过程、含有该2-取代咪唑[4,5-c]吡啶的药物组合物，以及利用该2-取代咪唑[4,5-c]吡啶来调节宿主动物（包括人类）骨产生和骨吸收之间的平衡。

  公开号：

  US05288871A1

文献信息

• Structure-activity evaluation of new uracil-based non-nucleoside inhibitors of HIV reverse transcriptase
  作者：Elena S. Matyugina、Vladimir T. Valuev-Elliston、Alexander N. Geisman、Mikhail S. Novikov、Alexander O. Chizhov、Sergey N. Kochetkov、Katherine L. Seley-Radtke、Anastasia L. Khandazhinskaya

  DOI：10.1039/c3md00225j

  日期：——

  A new series of potential nonnucleoside inhibitors of HIV-1 reverse transcriptase (NNRTIs) based on the carbocyclic 5′-nor-uracil scaffold were designed and synthesized. Three different aspects of the scaffold were investigated: the effects of adding a linker between the carbocyclic and phenyl fragments, introduction of different substituents on the benzoyl residue and replacing the central carbocyclic ring with a benzyl group. Analogues of 2′,3′-dideoxy-2′,3′-didehydro-5′-nor-uridine, bearing 3,5-dichloro- or 3,5-dimethylbenzoyl groups, showed inhibitory activity against HIV-RT wild-type (IC50 5–10 μM) and mutants L100I (IC50 1.2–2.1 μM) and K103N (IC50 8–17 μM).

  我们设计并合成了一系列基于碳环 5′-or-uracil 支架的新型潜在 HIV-1 逆转录酶非核苷抑制剂（NNRTIs）。对该支架的三个不同方面进行了研究：在碳环和苯基片段之间添加连接物、在苯甲酰基残基上引入不同取代基以及用苄基取代中心碳环的效果。带有 3,5-二氯或 3,5-二甲基苯甲酰基的 2′,3′-二脱氧-2′,3′-二脱氢-5′-去甲尿苷的类似物对 HIV-RT 野生型（IC50 5-10 μM）和突变体 L100I（IC50 1.2-2.1 μM）及 K103N（IC50 8-17 μM）具有抑制活性。
• Substituted Aminoalkyl- and Amidoalkyl-Benzopyran Derivatives
  申请人：Carotti Angelo

  公开号：US20090005436A1

  公开（公告）日：2009-01-01

  This invention is related to novel aminoalkyl- and amidoalkyl-benzopyran derivatives of the following general formula (I) wherein: the group is a substituent in position 6 or 7 wherein: R is an aromatic mono- or bi-cyclic carbocyclic ring or a mono- or bi-cyclic heterocyclic ring radical, said rings being optionally substituted by one or two substituents selected from (C 1 -C 5 ) straight or branched alkyl, (C 1 -C 5 ) straight or branched alkoxy, hydroxy, halogen and trifluoromethyl; m is zero or an integer from 1 to 3; n, p, R 1 and R 2 are as herein indicated and R 3 and R 4 are both hydrogen or taken together represent an oxygen atom, and the pharmaceutically acceptable salts thereof. The compounds that are active as selective and reversible MAO-B inhibitors in vitro and in vivo, are useful as medicaments for the prevention and the treatment of CNS degenerative disorders.

  本发明涉及以下通式（I）的新型氨基烷基和酰胺烷基苯并吡喃衍生物： 其中：基团是6或7位的取代基，其中：R是芳香单环或双环碳环或单环或双环杂环基团，所述环可以选择地由一或两个取代基取代，所述取代基选择自（C1-C5）直链或支链烷基，（C1-C5）直链或支链烷氧基，羟基，卤素和三氟甲基；m为零或1至3的整数；n、p、R1和R2如本文所示，而R3和R4均为氢或一起代表氧原子，以及其药学上可接受的盐。 这些化合物在体外和体内作为选择性和可逆的MAO-B抑制剂具有活性，可用作预防和治疗中枢神经系统退行性疾病的药物。
• Discovery of a Novel Class of Potent Coumarin Monoamine Oxidase B Inhibitors: Development and Biopharmacological Profiling of 7-[(3-Chlorobenzyl)oxy]-4-[(methylamino)methyl]-2<i>H</i>-chromen-2-one Methanesulfonate (NW-1772) as a Highly Potent, Selective, Reversible, and Orally Active Monoamine Oxidase B Inhibitor
  作者：Leonardo Pisani、Giovanni Muncipinto、Teresa Fabiola Miscioscia、Orazio Nicolotti、Francesco Leonetti、Marco Catto、Carla Caccia、Patricia Salvati、Ramon Soto-Otero、Estefania Mendez-Alvarez、Celine Passeleu、Angelo Carotti

  DOI：10.1021/jm9010127

  日期：2009.11.12

  In an effort to discover novel selective monoamine oxidase (MAO) B inhibitors with favorable physicochemical and pharmacokinetic profiles, 7-[m-halogeno)benzyloxy]coumarins bearing properly selected polar substituents at position 4 were designed, synthesized, and evaluated as MAO inhibitors. Several compounds with MAO-B inhibitory activity in the nanomolar range and excellent MAO-B selectivity (selectivity index SI > 400) were identified. Structure-affinity relationships and docking simulations provided valuable insights into the enzyme-inhibitor binding interactions at position 4, which has been poorly explored. Furthermore, computational and experimental studies led to the identification and biopharmacological characterization of 7-[(3-chlorobenzyl)oxy]-4-[(methylamino)methyl]-2H-chromen-2-one methanesulfonate 22b (NW-1772) as an in vitro and in vivo potent and selective MAO-B inhibitor, with rapid blood-brain barrier penetration, short-acting and reversible inhibitory activity, slight inhibition of selected cytochrome P450s, and low in vitro toxicity. On the basis of this preliminary preclinical profile, inhibitor 22b might be viewed as a promising clinical candidate for the treatment of neurodegenerative diseases.
• Dynamic Combinatorial Mass Spectrometry Leads to Inhibitors of a 2-Oxoglutarate-Dependent Nucleic Acid Demethylase
  作者：Esther C. Y. Woon、Marina Demetriades、Eleanor A. L. Bagg、WeiShen Aik、Svetlana M. Krylova、Jerome H. Y. Ma、MunChiang Chan、Louise J. Walport、David W. Wegman、Kevin N. Dack、Michael A. McDonough、Sergey N. Krylov、Christopher J. Schofield

  DOI：10.1021/jm201417e

  日期：2012.3.8

  2-Oxoglutarate-dependent nucleic acid demethylases are of biological interest because of their roles in nucleic acid repair and modification. Although some of these enzymes are linked to physiology, their regulatory roles are unclear. Hence, there is a desire to develop selective inhibitors for them; we report studies on AlkB, which reveal it as being amenable to selective inhibition by small molecules. Dynamic combinatorial chemistry linked to mass spectrometric analyses (DCMS) led to the identification of lead compounds, one of which was analyzed by crystallography. Subsequent structure-guided studies led to the identification of inhibitors of improved potency, some of which were shown to be selective over two other 2OG oxygenases. The work further validates the use of the DCMS method and will help to enable the development of inhibitors of nucleic acid modifying 2OG oxygenases both for use as functional probes and, in the longer term, for potential therapeutic use.
• Inhibition of Monoamine Oxidases by Functionalized Coumarin Derivatives:  Biological Activities, QSARs, and 3D-QSARs
  作者：Carmela Gnerre、Marco Catto、Francesco Leonetti、Peter Weber、Pierre-Alain Carrupt、Cosimo Altomare、Angelo Carotti、Bernard Testa

  DOI：10.1021/jm001028o

  日期：2000.12.1

  A large series of coumarin derivatives (71 compounds) were tested for their monoamine oxidase A and B (MAO-A and MAO-B) inhibitory activity. Most of the compounds acted preferentially on MAO-B with IC50 values in the micromolar to low-nanomolar range; high inhibitory activities toward MAO-A were also measured for sulfonic acid esters. The most active compound was 7-[(3,4-difluorobenzyl)oxy]-3,4-dimethylcoumarin, with an IC50 value toward MAO-B of 1.14 nM. A QSAR study of 7-X-benzyloxy meta-substituted 3,4-dimethylcoumarin derivatives acting on MAO-B yielded good statistical results (q(2) = 0.72, r(2) = 0.86), revealing the importance of lipophilic interactions in modulating the inhibition and excluding any dependence on electronic properties. CoMFA was performed on two data sets of MAO-A and MAO-B inhibitors. The GOLPE procedure, with variable selection criteria, was applied to improve the predictivity of the models and to facilitate the graphical interpretation of results.