3,5-bis-((Z)-3,4-dichloro-benzylidene)-tetrahydro-thiopyran-4-one | 61448-82-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5-bis-((Z)-3,4-dichloro-benzylidene)-tetrahydro-thiopyran-4-one
• 英文别名: 3,5-Bis(3,4-dichlorobenzylidene)tetrahydro-4H-thiopyran-4-one；(3Z,5Z)-3,5-bis[(3,4-dichlorophenyl)methylidene]thian-4-one
• CAS: 61448-82-6
• 化学式: C₁₉H₁₂Cl₄OS
• 分子量: 430.182
• InChiKey: FWWIOOPALCMIRN-ACFHMISVSA-N

物化性质

• 熔点：
  151-152.5 °C
• 沸点：
  627.8±55.0 °C(Predicted)
• 密度：
  1.505±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5-bis-((Z)-3,4-dichloro-benzylidene)-tetrahydro-thiopyran-4-one 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 以100%的产率得到3,5-Bis-[1-(3,4-dichloro-phenyl)-meth-(Z)-ylidene]-tetrahydro-thiopyran-4-ol
  参考文献：
  名称：

  2,6-Bis(3,4,5-trihydroxybenzylydene) derivatives of cyclohexanone

  摘要：

  A number of 2,6-bisbenzylidenecyclohexane-1-one derivatives have been synthesized and tested as HIV-1 integrase (IN) inhibitors with the aim of obtaining compounds capable to elicit antiviral activity at non-cytotoxic concentrations in cell-based assays. 3,5-Bis(3,4,5-trihydroxybenzylidene)-4-oxocyclohexaneacetic acid (20d) resulted one of the most potent and selective derivatives in acutely infected MT-4 cells (EC50 and CC50 values of 2 and 40 muM, respectively). In enzyme assays with recombinant HIV-1 integrase (rIN), this compound proved able to inhibit both 3'-processing and disintegration with IC50 values of 0.2 and 0.5 muM, respectively. In order to develop a model capable to predict the anti HIV-IN activity and useful to design novel derivatives, we performed a comparative molecular field analysis (CoMFA) like 3-D-QSAR. In our model the ligands were described quantitatively in the GRID program, and the model was optimized by selecting only the most informative variables in the GOLPE program. We found the predictive ability of the model to increase significantly when the number of variables was reduced from 20,925 to 1327. A Q(2) of 0.73 was obtained with the final model, confirming the predictive ability of the model. By studying the PLS coefficients in informative 3-D contour plots, ideas for the synthesis of new compounds could be generated. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.10.005
• 作为产物：
  描述：

  四氢噻喃-4-酮 、 3,4-二氯苯甲醛 在 盐酸 作用下， 以 乙醇 为溶剂， 以68%的产率得到3,5-bis-((Z)-3,4-dichloro-benzylidene)-tetrahydro-thiopyran-4-one
  参考文献：
  名称：

  六氢噻喃并[4,3-c]吡唑及其类似物的合成和抗炎活性。

  摘要：

  制备了一系列新颖的六氢硫代吡喃并[4,3-c]吡唑及其相关类似物，并通过使用小鼠活跃的Arthus反应和豚鼠的迟发型超敏反应皮肤反应作为初步筛选来测试其抗炎活性。在佐剂诱发的关节炎模型中进一步测试了最感兴趣的化合物18和28。在该系统中，两种化合物在腹膜内给药时均具有活性，但在以亚毒性剂量口服时则不能产生明显的活性。

  DOI：

  10.1021/jm00354a018

文献信息

• Synthesis and antiinflammatory activity of hexahydrothiopyrano[4,3-c]pyrazoles and related analogs
  作者：George C. Rovnyak、Robert C. Millonig、Joseph Schwartz、Virginia Shu

  DOI：10.1021/jm00354a018

  日期：1982.12

  A series of novel hexahydrothiopyrano[4,3-c]pyrazoles and related analogues were prepared and tested for antiinflammatory activity by using the mouse active Arthus reaction and the delayed hypersensitivity skin reaction in guinea pigs as primary screens. The compounds of most interest, 18 and 28, were further tested in a model of adjuvant-induced arthritis; in this system, both compounds were active

  制备了一系列新颖的六氢硫代吡喃并[4,3-c]吡唑及其相关类似物，并通过使用小鼠活跃的Arthus反应和豚鼠的迟发型超敏反应皮肤反应作为初步筛选来测试其抗炎活性。在佐剂诱发的关节炎模型中进一步测试了最感兴趣的化合物18和28。在该系统中，两种化合物在腹膜内给药时均具有活性，但在以亚毒性剂量口服时则不能产生明显的活性。
• Compounds for treating inflammatory and hyperproliferative diseases
  申请人：Board of Regents, The University of Texas System

  公开号：US10208012B2

  公开（公告）日：2019-02-19

  Compounds are provided that can exhibit anti-cancer and/or anti-inflammatory properties, in some aspects, methods of treating an inflammatory disease or a hyperproliferative disease, such as cancer, with the compounds are provided.

  所提供的化合物具有抗癌和/或抗炎特性，在某些方面，还提供了用这些化合物治疗炎症性疾病或过度增殖性疾病（如癌症）的方法。
• Preparation of thiopyrano- and pyrano[4,3-c]pyrazoles. Structure elucidation of dehydro coproducts
  作者：George C. Rovnyak、Virginia Shu

  DOI：10.1021/jo01328a041

  日期：1979.7
• ROVNYAK G. C.; SHU V., J. ORG. CHEM., 1979, 44, NO 14, 2518-2522
  作者：ROVNYAK G. C.、 SHU V.

  DOI：——

  日期：——
• ROVNYAK, G. C.;MILLONIG, R. C.;SCHWARTZ, J.;SHU, V., J. MED. CHEM., 1982, 25, N 12, 1482-1488
  作者：ROVNYAK, G. C.、MILLONIG, R. C.、SCHWARTZ, J.、SHU, V.

  DOI：——

  日期：——