methyl 4-(4-chlorobutanoyl)benzoate | 1050369-52-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-(4-chlorobutanoyl)benzoate
• 英文别名: Methyl 4-(4-chlorobutanoyl)benzoate
• CAS: 1050369-52-2
• 化学式: C₁₂H₁₃ClO₃
• 分子量: 240.686
• InChiKey: XCVSJHFUCGJPCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 4-(4-chlorobutanoyl)benzoate 在 dimethyl sulfide borane 、 (R)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 以97%的产率得到methyl (S)-4-(4-chloro-1-hydroxybutyl)benzoate
  参考文献：
  名称：

  Asymmetric Synthesis of Inhibitors of Glycinamide Ribonucleotide Transformylase

  摘要：

  Glycinamide ribonucleotide transformylase (GAR Tfase) catalyzes the first of two formyl transfer steps in the de novo purine biosynthetic pathway that require folate cofactors and has emerged as a productive target for antineoplastic therapeutic intervention. The asymmetric synthesis and evaluation of the two diastereomers of 10-methylthio-DDACTHF (10R-3 and 10S-3) and related analogues as potential inhibitors of GAR Tfase are reported. This work, which defines the importance of the C10 stereochemistry for this class of inhibitors of GAR Tfase, revealed that both diastereomers are potent inhibitors of rhGAR Tfase (10R-3 K-i = 210 nM, 10S-3 K-i = 180 nM) that exhibit effective cell growth inhibition (CCRF-CEM IC50 80 and 50 nM, respectively), which is dependent on intracellular polyglutamation by folylpolyglutamate synthetase (FPGS) but not intracellular transport by the reduced folate carrier.

  DOI：

  10.1021/jm800555h
• 作为产物：
  描述：

  methyl 4-(1,3-dithian-2-yl)benzoate 在 sodium hexamethyldisilazane 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 1.5h， 生成 methyl 4-(4-chlorobutanoyl)benzoate
  参考文献：
  名称：

  METHODS AND COMPOSITIONS FOR TREATING INFECTION

  摘要：

  本文提供了用于治疗或预防感染的组合物和方法。

  公开号：

  US20150238473A1

文献信息

• Manganese-Catalyzed Electrochemical Deconstructive Chlorination of Cycloalkanols via Alkoxy Radicals
  作者：Benjamin D. W. Allen、Mishra Deepak Hareram、Alex C. Seastram、Tom McBride、Thomas Wirth、Duncan L. Browne、Louis C. Morrill

  DOI：10.1021/acs.orglett.9b03652

  日期：2019.11.15

  A manganese-catalyzed electrochemical deconstructive chlorination of cycloalkanols has been developed. This electrochemical method provides access to alkoxy radicals from alcohols and exhibits a broad substrate scope, with various cyclopropanols and cyclobutanols converted into synthetically useful β- and γ-chlorinated ketones (40 examples). Furthermore, the combination of recirculating flow electrochemistry

  已经开发了锰催化的环烷醇的电化学解构氯化法。这种电化学方法可从醇中获得烷氧基，并具有广泛的底物范围，可将各种环丙醇和环丁醇转化为可合成使用的β-和γ-氯化酮（40个实例）。此外，采用循环流电化学和连续在线纯化的组合以克为单位获得产物。
• Methods and compositions for treating infection
  申请人：UNIVERSITY OF ROCHESTER

  公开号：US10004701B2

  公开（公告）日：2018-06-26

  Provided herein are compositions and methods for treating or preventing infection.

  本文提供了用于治疗或预防感染的组合物和方法。
• Repurposing the Antihistamine Terfenadine for Antimicrobial Activity against <i>Staphylococcus aureus</i>
  作者：Jessamyn I. Perlmutter、Lauren T. Forbes、Damian J. Krysan、Katherine Ebsworth-Mojica、Jennifer M. Colquhoun、Jenna L. Wang、Paul M. Dunman、Daniel P. Flaherty

  DOI：10.1021/jm5010682

  日期：2014.10.23

  Staphylococcus aureus is a rapidly growing health threat in the U.S., with resistance to several commonly prescribed treatments. A high-throughput screen identified the antihistamine terfenadine to possess, previously unreported, antimicrobial activity against S. aureus and other Gram-positive bacteria. In an effort to repurpose this drug, structure-activity relationship studies yielded 84 terfenadine-based analogues with several modifications providing increased activity versus S. aureus and other bacterial pathogens, including Mycobacterium tuberculosis. Mechanism of action studies revealed these compounds to exert their antibacterial effects, at least in part, through inhibition of the bacterial type II topoisomerases. This scaffold suffers from hERG liabilities which were not remedied through this round of optimization; however, given the overall improvement in activity of the set, terfenadine-based analogues provide a novel structural class of antimicrobial compounds with potential for further characterization as part of the continuing process to meet the current need for new antibiotics.