(3Z,5Z)-tetrahydro-3,5-bis((pyridine-3-yl)methylene)thiopyran-4-one | 83319-95-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻烷
• 英文名称: (3Z,5Z)-tetrahydro-3,5-bis((pyridine-3-yl)methylene)thiopyran-4-one
• 英文别名: (3Z,5Z)-tetrahydro-3,5-bis[(pyridine-3-yl)methylene]thiopyran-4-one；(3E,5E)-3,5-bis(pyridine-3-methylene)-tetrahydrothiopyran-4-one；(3E,5E)-3,5-bis(pyridin-3-ylmethylene)-tetrahydrothiopyran-4-one；(3Z,5Z)-3,5-bis(pyridin-3-ylmethylidene)thian-4-one
• CAS: 83319-95-3
• 化学式: C₁₇H₁₄N₂OS
• 分子量: 294.377
• InChiKey: WZLRTSDVMNMHBC-BGPOSVGRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  68.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3Z,5Z)-tetrahydro-3,5-bis((pyridine-3-yl)methylene)thiopyran-4-one 在 溶剂黄146 、 肼 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 1.33h， 生成 2-acetyl-2,3,3a,4,6,7-hexahydro-3-(3-pyridinyl)-7-[(3-pyridinyl)methylene]thiopyrano[4,3-c]pyrazole
  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
• 作为产物：
  描述：

  3-吡啶甲醛 、 四氢噻喃-4-酮 在 magnesium bromide ethyl etherate 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 2.5h， 以81%的产率得到(3Z,5Z)-tetrahydro-3,5-bis((pyridine-3-yl)methylene)thiopyran-4-one
  参考文献：
  名称：

  一种高效无溶剂合成吡喃酮和噻喃酮双芳基亚甲基的方法

  摘要：

  在室温下，在溴化镁乙基醚合物、三乙胺和甲醇的存在下，在无溶剂条件下，描述了杂环酮与各种芳香醛的显着有效的双交叉羟醛缩合反应。吡喃酮和噻喃酮的 3,5-二芳基亚甲基的优异产率是通过简单的一锅通用程序实现的。© 2007 Wiley Periodicals, Inc. 杂原子化学 18:44–49, 2007; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20252

  DOI：

  10.1002/hc.20252

文献信息

• [EN] CURCUMIN ANALOGS AND METHODS OF USE THEREOF<br/>[FR] ANALOGUES DE LA CURCUMINE ET PROCÉDÉS D'UTILISATION
  申请人：UNIV RUTGERS

  公开号：WO2012021692A1

  公开（公告）日：2012-02-16

  Curcumin analogs and methods of use thereof are provided.

  提供了姜黄素类似物及其使用方法。
• An Efficient and Improved Method for the Synthesis of Bis(arylmethylidene)thiopyranones
  作者：M. Saeed Abaee、Mohammad M. Mojtahedi、M. Mehdi Zahedi

  DOI：10.1055/s-2005-872656

  日期：——

  aldehydes with tetrahydrothiopyran-4-one in the presence of N-(trimethylsilyl)diethylamine and 5 M lithium perchlorate in diethyl ether at room temperature is described. Excellent yields of 3,5-bis(arylmethylidene)thiopyranones are achieved in a facile one-pot general procedure.

  描述了在室温下，在 N-（三甲基甲硅烷基）二乙胺和 5 M 高氯酸锂的二乙醚存在下，多种芳香醛与四氢噻喃-4-酮的双交叉羟醛缩合反应。3,5-双（芳基亚甲基）噻喃酮的高产率是通过简单的一锅通用程序实现的。
• Synthesis and evaluation of curcumin-related compounds for anticancer activity
  作者：Xingchuan Wei、Zhi-Yun Du、Xi Zheng、Xiao-Xing Cui、Allan H. Conney、Kun Zhang

  DOI：10.1016/j.ejmech.2012.04.005

  日期：2012.7

  Sixty-one curcumin-related compounds were synthesized and evaluated for their anticancer activity toward cultured prostate cancer PC-3 cells, pancreas cancer Panc-1 cells and colon cancer HT-29 cells. Inhibitory effects of these compounds on the growth of PC-3. Panc-1 and HT-29 cells were determined by the MTT assay. Compounds E10, F10, FN1 and FN2 exhibited exceptionally potent inhibitory effects on the growth of cultured PC-3, Panc-1 and HT-29 cells. The IC50 for these compounds was lower than 1 mu M in all three cell lines. E10 was 72-, 46- and 117-fold more active than curcumin for inhibiting the growth of PC-3, Panc-1 and HT-29 cells, respectively. F10 was 69-, 34- and 72-fold more active than curcumin for inhibiting the growth of PC-3, Panc-1 and HT-29 cells, respectively. FN1 and FN2 had about the same inhibitory effect as E10 and F10 toward Panc-1 cells but were less active than E10 and F10 toward PC-3 and HT-29 cells. The active compounds were potent stimulators of apoptosis. The present study indicates that E10, F10, FN1 and FN2 may have useful anticancer activity. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Synthesis of Bis(arylmethylidene)thiopyranones and Crystal Structure of the Phenyl Derivative
  作者：M. Saeed Abaee、Mohammad M. Mojtahedi、M. Mehdi Zahedi、A. Wahid Mesbah、Nafiseh Mohaddes Ghandchi、Werner Massa

  DOI：10.1080/10426500701542759

  日期：2007.10.18

  A convenient method is offered for double aldol condensation of tetrahydrothiopyran-4-one with aromatic aldehydes under LiBr catalysis. An X-ray analysis verifies the proposed structures.
• 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：——