(3Z,5Z)-3,5-bis[(4-methylphenyl)methylene]tetrahydro-4H-thiopyran-4-one 1,1-dioxide | 70343-39-4

• 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: (3Z,5Z)-3,5-bis[(4-methylphenyl)methylene]tetrahydro-4H-thiopyran-4-one 1,1-dioxide
• 英文别名: 3,5-bis-((Z)-4-methyl-benzylidene)-1,1-dioxo-tetrahydro-1λ⁶-thiopyran-4-one；(3Z,5Z)-3,5-bis[(4-methylphenyl)methylidene]-1,1-dioxothian-4-one
• CAS: 70343-39-4
• 化学式: C₂₁H₂₀O₃S
• 分子量: 352.454
• InChiKey: GIPGGNDYQHJDEB-AYKLPDECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  59.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3Z,5Z)-3,5-bis[(4-methylphenyl)methylene]tetrahydro-4H-thiopyran-4-one 1,1-dioxide 在 邻四氯苯醌 作用下， 以 甲醇 、 四氯化碳 为溶剂， 反应 1.5h， 生成 7-((Z)-4-methyl-benzylidene)-2-propyl-3-p-tolyl-2,4,6,7-tetrahydro-thiopyrano[4,3-c]pyrazole 5,5-dioxide
  参考文献：
  名称：

  Preparation of thiopyrano- and pyrano[4,3-c]pyrazoles. Structure elucidation of dehydro coproducts

  摘要：

  DOI：

  10.1021/jo01328a041
• 作为产物：
  描述：

  对甲基苯甲醛 、 四氢噻喃-4-酮 1,1-二氧化物 在 盐酸 作用下， 以 乙醇 为溶剂， 以82%的产率得到(3Z,5Z)-3,5-bis[(4-methylphenyl)methylene]tetrahydro-4H-thiopyran-4-one 1,1-dioxide
  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, Characterization, and Optimization for in Vivo Delivery of a Nonselective Isopeptidase Inhibitor as New Antineoplastic Agent
  作者：Ulma Cersosimo、Andrea Sgorbissa、Carmen Foti、Sara Drioli、Rosario Angelica、Andrea Tomasella、Raffaella Picco、Marta Stefania Semrau、Paola Storici、Fabio Benedetti、Federico Berti、Claudio Brancolini

  DOI：10.1021/jm501336h

  日期：2015.2.26

  Bis-arylidenecycloalkanones structurally related to the nonselective isopeptidase inhibitor G5 were synthesized and tested for cytotoxic activity against glioblastoma cells. Cytotoxicities correlate well with Hammett s constants for substituted arylidene groups, confirming the proposed inhibition mechanism. A new inhibitor (2c) based on the 4-hydroxycyclohexanone scaffold, which favors apoptosis over necrosis, was selected for further development. 2c inhibited representative deubiquitinases with micromolar IC50, and its proapoptotic activity was studied on several cancer cell lines. Inhibitor 2c was conjugated to PEG via dicarbamate and diester linkers. While the dicarbamate was inactive, the diester (2cPE) behaves like a prodrug and is converted into the active species 2c by secreted esterase activities. Finally, 2cPE was also tested in vivo on A549 lung carcinoma xenografts generated in mice. Intravenous treatment with 2cPE led to a significant reduction in primary tumor growth, without appreciable toxicity to mice.
• US4178379A
  申请人：——

  公开号：US4178379A

  公开（公告）日：1979-12-11
• 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。
• 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