N-benzyl-2-oxo-4-((4-(trifluoromethyl)phenyl)thio)azetidine-1-carboxamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: N-benzyl-2-oxo-4-((4-(trifluoromethyl)phenyl)thio)azetidine-1-carboxamide
• 英文别名: N-benzyl-2-oxo-4-[4-(trifluoromethyl)phenyl]sulfanylazetidine-1-carboxamide
• 化学式: C₁₈H₁₅F₃N₂O₂S
• 分子量: 380.391
• InChiKey: LTJBZJNEBVNAKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  74.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-(三氟甲基)苯硫酚 在 碳酸氢钠 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 12.0h， 生成 N-benzyl-2-oxo-4-((4-(trifluoromethyl)phenyl)thio)azetidine-1-carboxamide
  参考文献：
  名称：

  Non-transpeptidase binding arylthioether β-lactams active against Mycobacterium tuberculosis and Moraxella catarrhalis

  摘要：

  The prevalence of drug resistance in both clinical and community settings as a consequence of alterations of biosynthetic pathways, enzymes or cell wall architecture is a persistent threat to human health. We have designed, synthesized, and tested a novel class of non-transpeptidase, beta-lactamase resistant monocyclic beta-lactams that carry an arylthio group at C4. These thioethers exhibit inhibitory and cidal activity against serine beta-lactamase producing Mycobacterium tuberculosis wild type strain (Mtb) and multiple (n = 8) beta-lactamase producing Moraxella catarrhalis clinical isolates. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.11.025

文献信息

• [EN] SMALL MOLECULE ACTIVATORS AND INHIBITORS OF LECITHIN: CHOLESTEROL ACYLTRANSFERASE<br/>[FR] ACTIVATEURS ET INHIBITEURS DE PETITES MOLÉCULES DE LÉCITHINE-CHOLESTÉROL ACYLTRANSFÉRASE
  申请人：US HEALTH

  公开号：WO2015179293A1

  公开（公告）日：2015-11-26

  The disclosure includes compounds and salts of Formula I, II, and III. The variables R, R0, R1, R10, R11, and R2 are defined herein. Compounds and salts of Formula I, II, and III are useful as modulators of Lecithin: cholesterol acyltransferase (LCAT), a protein that mediates the transfer of fatty acids from lecithin to cholesterol to form cholesterol ester and lysolecithin. LCAT activators of Formula I, II, and III are useful for modulating HDL cholesterol levels and for treating genetic disorders caused by LCAT mutations such as familial LCAT deficiency. Some compounds and salts of Formula I, II, and III are also useful for treating diseases in which LCAT inhibition is desirable, such as lysosomal acid lipase deficiency and Wolman's disease. The disclosure also includes pharmaceutical compositions and method of treatment employing a compound of Formula I, II, or III.

  该披露包括公式I、II和III的化合物和盐。变量R、R0、R1、R10、R11和R2在此处被定义。公式I、II和III的化合物和盐可用作卵磷脂：胆固醇酰基转移酶（LCAT）的调节剂，LCAT是一种介导从卵磷脂向胆固醇转移脂肪酸以形成胆固醇酯和溶血卵磷脂的蛋白质。公式I、II和III的LCAT激活剂可用于调节HDL胆固醇水平，并用于治疗由LCAT突变引起的遗传疾病，如家族性LCAT缺乏症。公式I、II和III的一些化合物和盐也可用于治疗需要LCAT抑制的疾病，如溶酶体酸性脂肪酶缺乏症和沃尔曼氏病。该披露还包括使用公式I、II或III的化合物的药物组合物和治疗方法。
• Non-transpeptidase binding arylthioether β-lactams active against Mycobacterium tuberculosis and Moraxella catarrhalis
  作者：Tim N. Beck、Dina Lloyd、Rostislav Kuskovsky、Jeanette Minah、Kriti Arora、Balbina J. Plotkin、Jacalyn M. Green、Helena I. Boshoff、Clifton Barry、Jeffrey Deschamps、Monika I. Konaklieva

  DOI：10.1016/j.bmc.2014.11.025

  日期：2015.2

  The prevalence of drug resistance in both clinical and community settings as a consequence of alterations of biosynthetic pathways, enzymes or cell wall architecture is a persistent threat to human health. We have designed, synthesized, and tested a novel class of non-transpeptidase, beta-lactamase resistant monocyclic beta-lactams that carry an arylthio group at C4. These thioethers exhibit inhibitory and cidal activity against serine beta-lactamase producing Mycobacterium tuberculosis wild type strain (Mtb) and multiple (n = 8) beta-lactamase producing Moraxella catarrhalis clinical isolates. (C) 2014 Elsevier Ltd. All rights reserved.