2-chloro-N-(3-fluorobenzyl)acetamide | 330679-40-8

• 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-chloro-N-(3-fluorobenzyl)acetamide
• 英文别名: N-(3-fluorobenzyl)-2-chloroacetamide；2-chloro-N-[(3-fluorophenyl)methyl]acetamide
• CAS: 330679-40-8
• 化学式: C₉H₉ClFNO
• 分子量: 201.628
• InChiKey: ZDJJDJFJYVGNJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-chloro-N-(3-fluorobenzyl)acetamide 在 sodium hydride 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 、 mineral oil 为溶剂， 反应 75.17h， 生成 N-(3-fluorobenzyl)-2-[3-(4-chloro-3-fluorophenyl)-5-ethyl-1H-1,2,4-triazol-1-yl]acetamide
  参考文献：
  名称：

  [EN] TRIAZOLE DERIVATIVES AND THEIR USE AS PDE4 ACTIVATORS
  [FR] DÉRIVÉS DE TRIAZOLE ET LEUR UTILISATION COMME ACTIVATEURS DE PDE4

  摘要：

  提供了化学式(I)的化合物，这些化合物是长链环核苷酸磷酸二酯酶-4（PDE4）酶的激活剂。还描述了这些化合物的方法和用途，用于治疗或预防需要通过环3',5'-腺苷酸单磷酸（cAMP）介导的第二信使反应减少的疾病。

  公开号：

  WO2016151300A1
• 作为产物：
  描述：

  3-氟苄胺 、 氯乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.66h， 以5.15 g的产率得到2-chloro-N-(3-fluorobenzyl)acetamide
  参考文献：
  名称：

  [EN] COMPOUNDS AND THEIR USE AS PDE4 ACTIVATORS
  [FR] COMPOSÉS ET LEUR UTILISATION EN TANT QU'ACTIVATEURS DE PDE4

  摘要：

  Formula (I)的化合物是长形环核苷酸磷酸二酯酶-4（PDE4）酶（同工酶）的激活剂。还描述了这些化合物用于治疗或预防需要通过环3'，5'-腺苷酸单磷酸（cAMP）介导的第二信使反应减少的疾病的方法和用途。

  公开号：

  WO2018060704A1

文献信息

• Synthesis and Characterization of Novel<i>N</i>-(Phenyl, Benzyl, Hetaryl)-2-([1,2,4]Triazolo[1,5-<i>c</i>]Quinazolin-2-ylthio)Acetamides by Spectral Data, Antimicrobial Activity, Molecular Docking and QSAR Studies
  作者：Lyudmyla M. Antypenko、Sergiy I. Kovalenko、Tetyana S. Los'、Oksana L. Rebec'

  DOI：10.1002/jhet.2702

  日期：2017.3

  Candida albicans. N‐(4‐Fluorophenyl)‐2‐([1,2,4]triazolo[1,5‐c]quinazolin‐2‐ylthio)acetamide 3e had the best minimum inhibition zones against S. aureus and E. faecalis and 3‐[([1,2,4]triazolo[1,5‐c]quinazolin‐2‐ylthio)acetyl]amino}benzoic acid 3k – against E. coli, still in lower concentration, than references. By the means of in silico molecular docking into the active sites of E. faecalis dihydrofolate

  持久的新颖有效的抗微生物剂进行搜索，ñ - （苯基，苄基，杂芳基）-2 - （[1,2,4]三唑并[1,5- c ^ ]喹唑啉-2-基硫基）的合成乙酰胺，评价了结构（ LC-MS，IR，1 H-NMR谱和元素分析），并研究针对的抗菌活性的金黄色葡萄球菌，粪肠球菌，产气肠杆菌，阪坂崎，绿脓杆菌，大肠杆菌，和肺炎克雷伯氏菌，和抗真菌-反对白色念珠菌。N-（4-氟苯基）-2-（[[1,2,4]三唑[1,5-c ]喹唑啉-2-基硫基）乙酰胺3e对S的最小抑制区最好。 金黄色葡萄球菌和Ë。 粪肠球菌和3 - [（[1,2,4]三唑并[1,5- c ^ ]喹唑啉-2-基硫基）乙酰基]氨基}苯甲酸3K -反对ë。 大肠杆菌的浓度仍低于参考文献。通过计算机分子对接到E的活性位点。 粪便二氢叶酸还原酶和阴沟肠杆菌MyrA，建议可能的活动机制。计算了抗菌活性预测的定量构效关系模型。
• Substituted heterocyclic compounds
  申请人：——

  公开号：US20040152890A1

  公开（公告）日：2004-08-05

  Disclosed are novel heterocyclic derivatives, useful for the treatment of various disease states, in particular cardiovascular diseases such as atrial and ventricular arrhythmias, intermittent claudication, Prinzmetal's (variant) angina, stable and unstable angina, exercise induced angina, congestive heart disease, and myocardial infarction. The compounds are also useful in the treatment of diabetes.

  本发明涉及新型杂环衍生物，可用于治疗各种疾病状态，特别是心血管疾病，如心房和心室心律失常、间歇性跛行、普林兹梅特尔（变异型）心绞痛、稳定和不稳定性心绞痛、运动诱发性心绞痛、充血性心力衰竭和心肌梗塞。该化合物也可用于糖尿病的治疗。
• Triazole derivatives and their use as PDE4 activators
  申请人：MIRONID LIMITED

  公开号：US10385027B2

  公开（公告）日：2019-08-20

  Compounds of Formula (I), which are activators of long form cyclic nucleotide phosphodiesterase-4 (PDE4) enzymes, are provided. Methods and uses of these compounds for the treatment or prevention of disorders requiring a reduction of second messenger responses mediated by cyclic 3′,5′-adenosine monophosphate (cAMP) are also described.

  本发明提供了式(I)化合物，它们是长形环核苷酸磷酸二酯酶-4(PDE4)的激活剂。还描述了这些化合物治疗或预防需要减少由环 3′,5′-腺苷单磷酸（cAMP）介导的第二信使反应的疾病的方法和用途。
• Compounds and their use as PDE4 activators
  申请人：MIRONID LIMITED

  公开号：US11046660B2

  公开（公告）日：2021-06-29

  Compounds of Formula I, which are activators of long form cyclic nucleotide phosphodiesterase-4 (PDE4) enzymes (isoforms) are provided. Methods and uses of these compounds for the treatment or prevention of disorders requiring a reduction of second messenger responses mediated by cyclic 3′,5′-adenosine monophosphate (cAMP) are also described.

  本发明提供了式I化合物，它们是长形环核苷酸磷酸二酯酶-4（PDE4）酶（同工酶）的激活剂。还描述了这些化合物治疗或预防需要减少由环 3′,5′-腺苷单磷酸（cAMP）介导的第二信使反应的疾病的方法和用途。
• Discovery, synthesis and biological evaluation of 2-(4-(N-phenethylsulfamoyl)phenoxy)acetamides (SAPAs) as novel sphingomyelin synthase 1 inhibitors
  作者：Ya-li Li、Xiang-yu Qi、Hui Jiang、Xiao-dong Deng、Yan-ping Dong、Ting-bo Ding、Lu Zhou、Peng Men、Yong Chu、Ren-xiao Wang、Xian-cheng Jiang、De-yong Ye

  DOI：10.1016/j.bmc.2015.07.060

  日期：2015.9

  Sphingomyelin synthase (SMS) has been proved to be a potential drug target for the treatment of atherosclerosis. However, few SMS inhibitors have been reported. In this paper, structure-based virtual screening was performed on hSMS1. SAPA 1a was discovered as a novel SMS1 inhibitor with an IC50 value of 5.2 mu M in enzymatic assay. A series of 2-(4-(N-phenethylsulfamoyl)phenoxy)acetamides (SAPAs) were synthesized and their biological activities toward SMS1 were evaluated. Among them, SAPA 1j was found to be the most potent SMS1 inhibitor with an IC50 value of 2.1 mu M in in vitro assay. The molecular docking studies suggested the interaction modes of SMS1 inhibitors and PC with the active site of SMS1. Site-directed mutagenesis validated the involvement of residues Arg342 and Tyr338 in enzymatic sphingomyelin production. The discovery of SAPA derivatives as a novel class of SMS1 inhibitors would advance the development of more effective SMS1 inhibitors. (c) 2015 Elsevier Ltd. All rights reserved.