2-<2-(4-methylthiophenylthio)phenyl>acetic acid | 16175-07-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-<2-(4-methylthiophenylthio)phenyl>acetic acid
• 英文别名: <2-(4-methylthiophenylthio)phenyl>acetic acid；2-(2-(4-(methylthio)phenylthio)phenyl)acetic acid；2-(2-((4-chlorophenyl)thio)phenyl)acetic acid；<2-(4-Methylthiophenylthio)-phenyl>-essigsaeure；[2-(4-Methylthiophenylthio)-phenyl]-essigsaeure；2-[2-(4-Methylsulfanylphenyl)sulfanylphenyl]acetic acid
• CAS: 16175-07-8
• 化学式: C₁₅H₁₄O₂S₂
• 分子量: 290.407
• InChiKey: MJGUEUDQZMIOFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  87.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-<2-(4-methylthiophenylthio)phenyl>acetic acid 在 polyphosphoric acid (PPA) 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以77%的产率得到8-methylthiodibenzothiepin-10(11H)-one
  参考文献：
  名称：

  Identification of novel allosteric nonpeptidergic inhibitors of the human cytomegalovirus-encoded chemokine receptor US28

  摘要：

  Human cytomegalovirus ( HCMV) is a widespread human pathogen, possessing onco-modulatory properties. Constitutive signaling of the HCMV-encoded chemokine receptor US28 and its ability to bind a broad spectrum of chemokines might facilitate HCMV-associated tumor progression. Novel nonpeptidergic chemotypes were identified as neutral antagonists or inverse agonists on US28, that allosterically inhibit chemokine binding to US28. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.11.060
• 作为产物：
  描述：

  4-溴茴香硫醚 在 氢氧化钾 、 lithium aluminium tetrahydride 、 氯化亚砜 、 铜 作用下， 以 乙醚 、 乙醇 、 苯 为溶剂， 生成 2-<2-(4-methylthiophenylthio)phenyl>acetic acid
  参考文献：
  名称：

  Pelz,K. et al., Collection of Czechoslovak Chemical Communications, 1968, vol. 33, # 6, p. 1895 - 1910

  摘要：

  DOI：

文献信息

• Neuroleptics of the 8-methylthio-10-piperazino-10,11-dihydrodibenzo[b,f]thiepin series: New compounds and new procedures
  作者：Jiří Jílek、Josef Pomykáček、Antonín Dlabač、Marie Bartošová、Miroslav Protiva

  DOI：10.1135/cccc19800504

  日期：——

  Heating of 8-methylthiodibenzo[b,f]thiepin-10(11H)-one with mono-p-toluenesulfonates of 1-methylpiperazine and piperazine in vacuo led in good yields to the enamines IX-XI, the first of which was reduced with zinc and acetic acid to the base I (methiothepin). The ester III(oxyprothepindecanoate) was obtained by reaction of the amino alcohol II (oxyprothepin) with decanoic acid in the presence of N,N'-carbonyldiimidazole and by substitution of 10-chloro-8-methylthio-10,11-dihydrobenzo[b,f]thiepin with 1-(3-decanoyloxypropyl)piperazine. The substitution reaction of the same chloro compound with piperazine gave two stereoisomeric 1,4-disubstituted piperazines V. Reaction of the amino alcohol II with octyl isocyanate afforded the carbamate VI, an isoster of oxyprothepin decanoate (III). This substance showed in the test of antiapomorphine activity in dogs the properties of a long-acting antiemetic. Two new potential metabolites (XII, XIII) of compounds I-III were synthesized and new pharmacological data are given for two further potential metabolites (XIV, XV) of oxyprothepin (II).

  将8-甲硫基二苯并[b,f]噻吩-10(11H)-酮与1-甲基哌嗪和哌嗪的单-p-甲苯磺酸酯在真空中加热，产率良好地得到烯胺IX-XI，其中第一个被还原为基本物质I（甲硫噻吩）的烯胺被锌和乙酸处理。通过氨基醇II（氧丙硫噻吩）与癸酸在N,N'-碳酰二咪唑存在下反应，并通过用1-(3-癸酰氧丙基)哌嗪替代10-氯-8-甲硫基-10,11-二氢二苯并[b,f]噻吩制得酯III（氧丙硫噻吩癸酸酯）。同一氯化合物与哌嗪的取代反应得到两个立体异构体的1,4-二取代哌嗪V。氨基醇II与辛基异氰酸酯反应得到氨基甲酸酯VI，是氧丙硫噻吩癸酸酯（III）的同分异构体。该物质在狗的抗阿波吗啡活性测试中表现出长效抗恶心的特性。合成了化合物I-III的两种新潜在代谢物（XII, XIII），并为氧丙硫噻吩（II）的另外两种潜在代谢物（XIV, XV）提供了新的药理数据。
• Overcoming chloroquine resistance in malaria: Design, synthesis and structure–activity relationships of novel chemoreversal agents
  作者：Aicha Boudhar、Xiao Wei Ng、Chiew Yee Loh、Wan Ni Chia、Zhi Ming Tan、Francois Nosten、Brian W. Dymock、Kevin S.W. Tan

  DOI：10.1016/j.ejmech.2016.04.058

  日期：2016.8

  Malaria remains a significant infectious disease with even artemisinin-based therapies now facing resistance in the field. Development of new therapies is urgently needed, either by finding new compounds with unique modes of action, or by reversing resistance towards known drugs with 'chemosensitizers' or 'chemoreversal' agents (CRA). Concerning the latter, we have focused on the resistance mechanisms developed against chloroquine (CQ). We have synthesized a series of compounds related to previously identified CRAs, and found promising novel compounds. These compounds show encouraging results in a coumarin labeled chloroquine uptake assay, exhibiting a dose response in resensitising parasites to the antimalarial effects of chloroquine. Selected compounds show consistent potency across a panel of chloroquine and artemisinin sensitive and resistant parasites, and a wide therapeutic window. This data supports further study of CRAs in the treatment of malaria and, ultimately, their use in chloroquine-based combination therapies. (C) 2016 Elsevier Masson SAS. All rights reserved.
• Fluorinated tricyclic neuroleptics with prolonged effects: Some new 8-chloro-3-fluoro-10-piperazino-10,11-dihydrodibenzo[b,f]thiepins
  作者：M. Rajšner、E. Svátek、J. Metyšová、M. Bartošová、F. Mikšík、M. Protiva

  DOI：10.1135/cccc19773079

  日期：——
• Jilek,Jiri; Pomykacek, Josef; Prosek, Zdenek, Collection of Czechoslovak Chemical Communications, 1983, vol. 48, # 3, p. 906 - 927
  作者：Jilek,Jiri、Pomykacek, Josef、Prosek, Zdenek、Holubek, Jiri、Svatek, Emil、et al

  DOI：——

  日期：——
• JILEK J.; POMYKACEK J.; DLABAC A.; BARTOSOVA M., COLLECT. CZECH. CHEM. COMMUN., 1980, 45, NO 2, 504-516
  作者：JILEK J.、 POMYKACEK J.、 DLABAC A.、 BARTOSOVA M.

  DOI：——

  日期：——