methyl 2-(octylthio)acetate | 14091-30-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2-(octylthio)acetate
• 英文别名: methyl 3-thiaundecanoate；methyl 3-thioundecanoate；methyl n-octylthioacetate；1-Methoxycarbonylmethylmercapto-octan；Methyl 2-octylsulfanylacetate
• CAS: 14091-30-6
• 化学式: C₁₁H₂₂O₂S
• mdl: MFCD27944622
• 分子量: 218.36
• InChiKey: MQNVPMIYUCAAQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  14
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.909
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-(octylthio)acetate 在 lithium hydroxide 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以83%的产率得到2-辛基硫基乙酸
  参考文献：
  名称：

  硫发挥作用：新型硫醚官能化的咪唑鎓离子液晶的合成和介晶性质

  摘要：

  从2-巯基乙酸甲酯合成了新型硫醚连接的咪唑鎓离子液晶。通过差示扫描量热法（DSC），偏振光学显微镜（POM）和X射线衍射确定了介晶性质。所有的介晶均表现出具有强相互指状的双层结构的近晶A中间相几何形状。硫醚连接的咪唑鎓盐与相应的胺和酰胺连接的咪唑鎓盐以及简单的N-烷基咪唑鎓盐的比较表明，中间相宽度和稳定性均随着连接单元柔软度的增加而增加，从而表明了有益的作用。硫。另外，连接单元长度的增加减少了烷基链的叉指。

  DOI：

  10.1016/j.tet.2014.03.050
• 作为产物：
  描述：

  1-溴辛烷 、 巯基乙酸甲酯 在 potassium carbonate 作用下， 以 二甲基亚砜 、 丙酮 为溶剂， 反应 48.0h， 以96%的产率得到methyl 2-(octylthio)acetate
  参考文献：
  名称：

  硫发挥作用：新型硫醚官能化的咪唑鎓离子液晶的合成和介晶性质

  摘要：

  从2-巯基乙酸甲酯合成了新型硫醚连接的咪唑鎓离子液晶。通过差示扫描量热法（DSC），偏振光学显微镜（POM）和X射线衍射确定了介晶性质。所有的介晶均表现出具有强相互指状的双层结构的近晶A中间相几何形状。硫醚连接的咪唑鎓盐与相应的胺和酰胺连接的咪唑鎓盐以及简单的N-烷基咪唑鎓盐的比较表明，中间相宽度和稳定性均随着连接单元柔软度的增加而增加，从而表明了有益的作用。硫。另外，连接单元长度的增加减少了烷基链的叉指。

  DOI：

  10.1016/j.tet.2014.03.050

文献信息

• Quantitative aspects of radical addition. Part IV. Rate-constant ratios for addition of trichloromethyl and thiyl radicals to olefins
  作者：J. I. G. Cadogan、I. H. Sadler

  DOI：10.1039/j29660001191

  日期：——

  and trichloromethyl radicals from bromotrichloromethane. In a number of experiments both the unchanged olefins and the 1 : 1 adducts were estimated, thus accounting, for the first time, for all the olefin in the system. The results, while confirming the electrophilic character of the radicals studied, indicate that no single factor is entirely responsible for the variations in olefin reactivity. The absence

  考察了影响自由基加成至烯烃双键的速率的因素，并特别提到了极性，共振和空间现象的相对重要性。一种有效的竞争方法已被用来衡量取代反式的相对反应性-对苯二甲酸酯，取代的苯乙烯和各种脂族烯烃，它们来自硫代乙醇酸及其甲基酯的噻吩基，以及来自溴代三氯甲烷的三氯甲基基团。在许多实验中，估计了未改变的烯烃和1：1加合物，因此首次考虑了系统中所有烯烃。结果证实了所研究自由基的亲电特性，但表明没有单一因素完全负责烯烃反应性的变化。已经确定，在将硫代基团添加到取代的α-甲基苯乙烯中时，对过渡态没有明显的极性贡献。
• Redox Mediators in Visible Light Photocatalysis: Photocatalytic Radical Thiol–Ene Additions
  作者：Elizabeth L. Tyson、Zachary L. Niemeyer、Tehshik P. Yoon

  DOI：10.1021/jo500031g

  日期：2014.2.7

  useful radical thiol–ene reactions can be initiated by visible light irradiation in the presence of transition metal polypyridyl photocatalysts. The success of this method relies upon the use of p-toluidine as an essential additive. Using these conditions, high-yielding thiol–ene reactions of cysteine-containing biomolecules can be accomplished using biocompatibile wavelengths of visible light, under

  在过渡金属聚吡啶基光催化剂存在下，可以通过可见光照射引发合成有用的自由基硫醇-烯反应。这种方法的成功依赖于对甲苯胺作为基本添加剂的使用。使用这些条件，含半胱氨酸的生物分子的高产硫醇 - 烯反应可以使用可见光的生物相容性波长，在水性条件下，并以硫醇组分作为限制试剂来完成。我们提供的证据表明p甲苯胺作为氧化还原介质，能够催化硫醇以其他方式低效光氧化为关键的硫自由基中间体。因此，我们表明共催化氧化剂在涉及可见光光氧化还原催化的合成反应的设计中可能很重要。
• In Vitro Activity of a Novel Antimycobacterial Compound, <i>N</i> -Octanesulfonylacetamide, and Its Effects on Lipid and Mycolic Acid Synthesis
  作者：Nikki M. Parrish、Todd Houston、Paul B. Jones、Craig Townsend、James D. Dick

  DOI：10.1128/aac.45.4.1143-1150.2001

  日期：2001.4

  β-Sulfonyl carboxamides have been proposed to serve as transition-state analogues of the β-ketoacyl synthase reaction involved in fatty acid elongation. We tested the efficacy of N -octanesulfonylacetamide (OSA) as an inhibitor of fatty acid and mycolic acid biosynthesis in mycobacteria. Using the BACTEC radiometric growth system, we observed that OSA inhibits the growth of several species of slow-growing mycobacteria, including Mycobacterium tuberculosis (H37Rv and clinical isolates), the Mycobacterium avium complex (MAC), Mycobacterium bovis BCG, Mycobacterium kansasii , and others. Nearly all species and strains tested, including isoniazid and multidrug resistant isolates of M. tuberculosis , were susceptible to OSA, with MICs ranging from 6.25 to 12.5 μg/ml. Only three clinical isolates of M. tuberculosis (CSU93, OT2724, and 401296), MAC, and Mycobacterium paratuberculosis required an OSA MIC higher than 25.0 μg/ml. Rapid-growing mycobacterial species, such as Mycobacterium smegmatis, Mycobacterium fortuitum , and others, were not susceptible at concentrations of up to 100 μg/ml. A 2-dimensional thin-layer chromatography system showed that OSA treatment resulted in a significant decrease in all species of mycolic acids present in BCG. In contrast, mycolic acids in M. smegmatis were relatively unaffected following exposure to OSA. Other lipids, including polar and nonpolar extractable classes, were unchanged following exposure to OSA in both BCG and M. smegmatis . Transmission electron microscopy of OSA-treated BCG cells revealed a disruption in cell wall synthesis and incomplete septum formation. Our results indicate that OSA inhibits the growth of several species of mycobacteria, including both isoniazid-resistant and multidrug resistant strains of M. tuberculosis . This inhibition may be the result of OSA-mediated effects on mycolic acid synthesis in slow-growing mycobacteria or inhibition via an undescribed mechanism. Our results indicate that OSA may serve as a promising lead compound for future antituberculous drug development.

  摘要 β-磺酰基羧酰胺被认为是脂肪酸伸长过程中β-酮酰合成酶反应的过渡态类似物。我们测试了 N -辛烷磺酰乙酰胺（OSA）作为分枝杆菌脂肪酸和霉菌酸生物合成抑制剂的功效。利用 BACTEC 辐射生长系统，我们观察到 OSA 可抑制几种生长缓慢的分枝杆菌的生长，其中包括 结核分枝杆菌 (H37Rv 和临床分离株）、 分枝杆菌 复合菌（MAC） 牛分枝杆菌 卡介苗、 堪萨斯分枝杆菌 等。几乎所有检测过的菌种和菌株，包括对异烟肼和多种药物有抗药性的 结核分枝杆菌 对 OSA 敏感，其 MIC 值在 6.25 至 12.5 μg/ml 之间。只有三个临床分离的结核杆菌 结核杆菌 (结核分枝杆菌（CSU93、OT2724 和 401296）、MAC 和 副结核分枝杆菌 需要的 OSA MIC 值高于 25.0 μg/ml。快速生长的分枝杆菌，如 分枝杆菌等快速生长的分枝杆菌，如烟肉分枝杆菌、福氏分枝杆菌 等，在浓度高达 100 μg/ml 时也不敏感。二维薄层色谱系统显示，OSA 处理会导致卡介苗中所有种类的霉菌酸显著减少。相比之下，在 中的霉菌醇酸 中的霉酚酸则相对不受影响。其他脂类，包括极性和非极性可提取类，在暴露于 OSA 后在卡介苗和 M. smegmatis .经 OSA 处理的卡介苗细胞的透射电子显微镜显示，细胞壁的合成受到破坏，隔膜形成不完整。我们的研究结果表明，OSA 可抑制多种分枝杆菌的生长，包括耐异烟肼菌株和耐多药菌株的结核杆菌。 结核杆菌 .这种抑制作用可能是 OSA 介导的对生长缓慢的分枝杆菌中霉菌醇酸合成的影响，也可能是通过一种未被描述的机制产生的抑制作用。我们的研究结果表明，OSA 可作为未来抗结核药物开发的一种前景广阔的先导化合物。
• 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。
• A New Class of Antituberculosis Agents
  作者：Paul B. Jones、Nikki M. Parrish、Todd A. Houston、Anthony Stapon、Niharika P. Bansal、James D. Dick、Craig A. Townsend

  DOI：10.1021/jm000149l

  日期：2000.8.1

  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.