3-Decylsulfonylpropanamide

• 分子结构分类: 有机化合物 - 有机硫化合物 - 磺酰类
• 英文名称: 3-Decylsulfonylpropanamide
• 化学式: C₁₃H₂₇NO₃S
• 分子量: 277.428
• InChiKey: UXTVHQNLIVCFKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  85.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-癸硫醇 在 ammonium hydroxide 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 、 丙酮 为溶剂， 反应 54.0h， 生成 3-Decylsulfonylpropanamide
  参考文献：
  名称：

  A New Class of Antituberculosis Agents

  摘要：

  Long-chain lipid envelopes are characteristic of mycobacteria such as those that cause tuberculosis and leprosy. Inhibition of fatty acid synthesis or elongation is a strategy demonstrated to be clinically effective against M. tuberculosis. A new class of compounds designed to inhibit the beta-ketoacyl synthase reaction of fatty acid synthesis has been developed. Of >30 compounds described, the most active were acetamides containing alkylsulfonyl substituents. Inhibitory activities were acutely sensitive to net charge, chain length, and degree of unsaturation. The most active compound 5 (alkyl = C-10) contained a single methylene spacer between the sulfone and carboxamide and exhibited an MIC of 0.75-1.5 mu g/mL, comparable to first-line antituberculosis drugs. These compounds are species-specific, exhibiting no significant activity against bacterial species other than M. tuberculosis and closely related strains. The synthesis, biological activity, and specificity of these compounds are described.

  DOI：

  10.1021/jm000149l

文献信息

• Antimicrobial compounds
  申请人：The Johns Hopkins University of Medicine

  公开号：US20040186176A1

  公开（公告）日：2004-09-23

  This invention provides methods for treating a mycobacterial infection by administering to an animal a pharmaceutical composition containing a compound having the formula R—SO n -Z-CO—Y, where R is an alkyl group having 6-20 carbons; Z is a radical selected from —CH 2 —, —O—, and —NH—, two of these radicals coupled together, or —CH 2 ═CH 2 —; Y is —NH 2 , O—CH 2 —C 6 H 5 , —CO—CO—O—CH 3 , or O—CH 3 ; and n is 1 or 2. It has been discovered that these compounds inhibit growth of microbial cells which synthesize &agr;-substitued. &bgr;-hydroxy fatty acids, particularly corynemycolic acid, nocardic acid, and mycolic acid. These compounds may be used to inhibit growth of mycobacterial cells, such as Mycobacterium tuberculosis, drug-resistant M. tuberculosis, M. avium intracellulare, and M. leprae.

  本发明提供了一种通过向动物施用含有化合物R-SOn-Z-CO-Y的药物组合物来治疗分枝杆菌感染的方法，其中R是具有6-20个碳的烷基基团；Z是从-CH2-，-O-和-NH-中选择的基团，其中两个这些基团耦合在一起，或-CH2═CH2-；Y是-NH2，O-CH2-C6H5，-CO-CO-O-CH3或O-CH3；n为1或2。已经发现这些化合物抑制合成α-取代的β-羟基脂肪酸，特别是角质分枝杆菌酸，诺卡氏酸和酰胺分枝杆菌酸的微生物细胞的生长。这些化合物可用于抑制分枝杆菌细胞的生长，例如结核分枝杆菌，耐药性结核分枝杆菌，肺巨细胞分枝杆菌和麻风分枝杆菌。
• ANTIMICROBIAL COMPOUNDS
  申请人：THE JOHNS HOPKINS UNIVERSITY

  公开号：EP1007509B1

  公开（公告）日：2004-03-03
• US6713654B1
  申请人：——

  公开号：US6713654B1

  公开（公告）日：2004-03-30
• US7385086B2
  申请人：——

  公开号：US7385086B2

  公开（公告）日：2008-06-10
• [EN] ANTIMICROBIAL COMPOUNDS<br/>[FR] COMPOSES ANTIMICROBIENS
  申请人：——

  公开号：WO1999010321A2

  公开（公告）日：1999-03-04

  [EN] This invention provides methods for treating a mycobacterial infection by administering to an animal a pharmaceutical composition containing a compound having the formula R-SOn-Z-CO-Y, where R is an alkyl group having 6-20 carbons; Z is a radical selected from -CH2-, -O-, and -NH-, two of these radicals coupled together, or -CH2=CH2-; Y is -NH2, O-CH2-C6H5, -CO-CO-O-CH3, or O-CH3; and n is 1 or 2. It has been discovered that these compounds inhibit growth of microbial cells which synthesize alpha -substitued, beta -hydroxy fatty acids, particularly corynemycolic acid, nocardic acid, and mycolic acid. These compounds may be used to inhibit growth of mycobacterial cells, such as Mycobacterium tuberculosis, drug-resistant M. tuberculosis, M. avium intracellulare, and M. leprae.
  [FR] L'invention concerne des traitements pour les infections à mycobactéries, comprenant l'administration à un animal d'une composition pharmaceutique contenant un composé représenté par la formule R-SOn-Z-CO-Y, dans laquelle R est un groupe alkyle comprenant de 6 à 20 atomes de carbone; Z est un radical sélectionné parmi -CH2-, -O- et -NH-, deux de ces radicaux assemblés ou -CH2=CH2-; Y est -NH2, O-CH2-C6H5, -CO-CO-O-CH3 ou O-CH3; et n est 1 ou 2. On a découvert que ces composés inhibent le développement des cellules microbiennes qui synthétisent les acides gras beta -hydroxy substitués en alpha , en particulier l'acide corynemycolique, l'acide nocardique et l'acide mycolique. Ces composés peuvent êtres utilisés pour inhiber le développement de cellules mycobactériennes tells que Mycobacterium tuberculosis, M. tuberculosis pharmacorésistant, M. avium intracellulare et M. leprae.