4-acetylsulfanyl-2-methyl-3-oxopentanoic acid methyl ester | 95628-73-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 4-acetylsulfanyl-2-methyl-3-oxopentanoic acid methyl ester
• 英文别名: methyl 4-(acetylsulfanyl)-2-methyl-3-oxopentanoate；Methyl 4-acetylsulfanyl-2-methyl-3-oxopentanoate
• CAS: 95628-73-2
• 化学式: C₉H₁₄O₄S
• 分子量: 218.274
• InChiKey: QSYQSORGJBJALM-UHFFFAOYSA-N

物化性质

• 沸点：
  273.9±20.0 °C(Predicted)
• 密度：
  1.151±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  85.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-acetylsulfanyl-2-methyl-3-oxopentanoic acid methyl ester 在 氢氧化钾 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 3,5-dimethyl-4-(methoxymethoxy)-5H-thiophen-2-one
  参考文献：
  名称：

  化学酶法合成（5 S）-和（5 R）-羟甲基-3,5-二甲基-4-（甲氧基甲氧基）-5 H-噻吩-2-酮：硫菌素的前体及其绝对构型的确定

  摘要：

  进行了方便的对映选择性合成的（5 S）-和（5 R）-羟甲基-3,5-二甲基-4-（甲氧基甲氧基）-5 H-噻吩-2-酮，它是硫代催乳素合成中的关键中间体通过番木瓜脂肪酶介导的拆分方案分离得到94％ee的（R）-2和98％ee的对映体（S）-9。C-5位置的绝对构型已通过Mosher的方法确定。

  DOI：

  10.1016/j.tetasy.2006.10.032
• 作为产物：
  描述：

  2-甲基-3-氧代戊酸甲酯 在 溴 、 三乙胺 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 6.5h， 生成 4-acetylsulfanyl-2-methyl-3-oxopentanoic acid methyl ester
  参考文献：
  名称：

  新的喹啉-硫内酯缀合物作为潜在的抗结核和抗菌剂

  摘要：

  由于感染率和耐药性升高，结核病和细菌感染是主要挑战。需要开发新的化学试剂来解决这些问题。硫乳霉素和喹啉是新型抗结核和抗菌药物设计中很有前途的先导分子。在此，我们报告了一系列新型喹啉-硫内酯偶联物作为潜在的抗结核和抗菌剂的设计和合成。其中两种偶联物6b和6d表现出良好的抗结核活性，MIC 值为 8 µg/mL。对接研究表明，缀合物6b和6d对结核分枝杆菌的靶蛋白 KasA 表现出良好的结合亲和力. 另外两种结合物也显示出良好的抗菌活性，MIC 值为 8 µg/mL。此外，缀合物7a的对接优于标准药物利奈唑胺对三种不同分子受体的对接。

  DOI：

  10.1016/j.molstruc.2022.134099

文献信息

• Synthesis, antimalarial evaluation and molecular docking studies of some thiolactone derivatives
  作者：Jitendra Sainy、Rajesh Sharma

  DOI：10.1016/j.molstruc.2016.12.095

  日期：2017.4

  present study novel thiolactone derivatives were designed, synthesized and characterized by various analytical techniques such as IR, 1 H NMR, 13 C NMR, mass spectral data and elemental analysis. All synthesized compounds were evaluated for in vitro antimalarial activity against Dd2 and 3d7 strain of P. falciparum. All synthesized compounds were also subjected for molecular docking study with pf KASI/II

  摘要 在本研究中，新型硫内酯衍生物的设计、合成和表征采用各种分析技术，如红外、 1 H NMR、 13 C NMR、质谱数据和元素分析。评估了所有合成化合物对恶性疟原虫 Dd2 和 3d7 菌株的体外抗疟活性。所有合成的化合物也进行了与 pf KASI/II 酶的分子对接研究，以分析它们在酶活性位点的结合方向。发现化合物 5d、5e 和 5i 对 Dd2 菌株和 3D7 菌株的 IC 50 最有效，IC 50 范围分别为 0.09-0.19 μM 和 0.03-0.04 μM，并且它们与活性物质的残基显示出良好的结合亲和力pf KASI/II 的站点。
• Analogues of thiolactomycin as potential anti-malarial and anti-trypanosomal agents
  作者：S Jones

  DOI：10.1016/j.bmc.2003.11.023

  日期：2004.2.15

  A series of analogues of the naturally occurring antibiotic thiolactomycin (TLM) have been synthesised and evaluated for their ability to inhibit the growth of the malaria parasite, Plasmodium falciparum. Thiolactomycin is an inhibitor of Type II fatty acid synthase which is found in plants and most prokaryotes, but not an inhibitor of Type I fatty acid synthase in mammals. A number of the analogues showed inhibition equal to or greater than TLM. The introduction of hydrophobic alkyl groups at the C3 and C5 positions of the thiolactone ring lead to increased inhibition, the best showing a fourteenfold increase in activity over TLM. In addition, some of the analogues showed activity when assayed against the parasitic protozoa, Trypanosoma cruzi and Trypanosoma brucei. (C) 2003 Elsevier Ltd. All rights reserved.
• Synthesis and biological evaluation of a C5-biphenyl thiolactomycin library
  作者：Veemal Bhowruth、Alistair K. Brown、Suzanne J. Senior、John S. Snaith、Gurdyal S. Besra

  DOI：10.1016/j.bmcl.2007.07.082

  日期：2007.10

  Fifteen novel C5 analogues of thiolactomycin (13 biphenyl analogues and two biphenyl mimics) have been synthesised and assessed for their in vitro mtFabH and whole cell Mycobacterium bovis BCG activity, respectively. Analysis of the 15 compounds revealed that six possessed enhanced in vitro activity in a direct mtFabH assay. Encouragingly analogues 11, 12 and 13 gave a significant enhancement in in vitro activity against mtFabH. Analogue 13 (5-(4-methoxycarbonyl-biphenyl-4-ylmethyl)-4-hydroxy-3,5-dimethyl-5H-thiophen-2-one) gave an IC50 value of 3 mu M compared to the parent drug thiolactomycin (75 mu M) against mtFabH. The biological analysis of this library reaffirms the requirement for a linear pi-rich system containing hydrogen bond accepting substituents attached to the para-position of the C5 biphenyl analogue to generate compounds with enhanced activity. (c) 2007 Elsevier Ltd. All rights reserved.
• Antitubercular agents. Part 2: New thiolactomycin analogues active against Mycobacterium tuberculosis
  作者：Ahmed Kamal、Ahmad Ali Shaik、Rakesh Sinha、J.S. Yadav、Sudarshan K. Arora

  DOI：10.1016/j.bmcl.2005.01.084

  日期：2005.4

  Structurally modified analogues of naturally occurring antibiotic thiolactomycin, substituted at 4-position of the thiolactone ring have been prepared and evaluated for their antitubercular activity. Some of the compounds have exhibited potential activity against Mycobacterium tuberculosis. (c) 2005 Elsevier Ltd. All rights reserved.
• Total ssynthesis of (±) thiolactomycin
  作者：Chia-Lin J. Wang、J.M Salvino

  DOI：10.1016/s0040-4039(01)81574-4

  日期：——