3,5-dibenzylidene-4-piperidone hydrochloride | 54237-35-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3,5-dibenzylidene-4-piperidone hydrochloride
• 英文别名: 3,5-bis(benzylidene)-4-piperidone hydrochloride；3,5-dibenzylidene-piperidin-4-one; hydrochloride；3,5-Dibenzyliden-piperidin-4-on; Hydrochlorid；4-Piperidinone, 3,5-bis(phenylmethylene)-, hydrochloride；3,5-dibenzylidenepiperidin-4-one;hydrochloride
• CAS: 54237-35-3
• 化学式: C₁₉H₁₇NO*ClH
• 分子量: 311.811
• InChiKey: TUYFFZOIQLBJAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  22
• 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：
  29.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5-dibenzylidene-4-piperidone hydrochloride 在 乙醇 、 铂 作用下， 生成 3,5-dibenzyl-piperidin-4-ol
  参考文献：
  名称：

  McElvain; McMahon, Journal of the American Chemical Society, 1949, vol. 71, p. 901,904

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氧代哌啶酮盐酸盐 、 苯甲醛 在 盐酸 、 溶剂黄146 作用下， 反应 48.0h， 生成 3,5-dibenzylidene-4-piperidone hydrochloride
  参考文献：
  名称：

  CLEFMA—An anti-proliferative curcuminoid from structure–activity relationship studies on 3,5-bis(benzylidene)-4-piperidones

  摘要：

  3,5-Bis(benzylidene)-4-piperidones are being advanced as synthetic analogs of curcumin for anti-cancer and anti-inflammatory properties. We performed structure-activity relationship studies, by testing several synthesized 3,5-bis(benzylidene)-4-piperidones for anti-proliferative activity in lung adenocarcinoma H441 cells. Compared to the lead compound 1, or 3,5-bis(2-fluorobenzylidene)-4-piperidone, five compounds were found to be more potent (IC50 <30 mu M), and 16 compounds possessed reduced cell-killing efficacy (IC50 >50 mu M). Based on the observations, we synthesized 4-[3,5-bis(2-chlorobenzyl-idene-4-oxo-piperidine-1-yl)-4-oxo-2-butenoic acid] (29 or CLEFMA) as a novel analog of 1. CLEFMA was evaluated for anti-proliferative activity in H441 cells, and was found to be several folds more potent than compound 1. We did not find apoptotic cell population in flow cytometry, and the absence of apoptosis was confirmed by the lack of caspase cleavage. The electron microscopy of H441cells indicated that CLEFMA and compound 1 induce autophagic cell death that was inhibited by specific autophagy inhibitor 3-methyladenine. The results suggest that the potent and novel curcuminoid, CLEFMA, offers an alternative mode of cell death in apoptosis-resistant cancers. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.055

文献信息

• 5-Substituted-pyrazolo(4,3-c)pyridines
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US03931169A1

  公开（公告）日：1976-01-06

  Compounds of the formula ##SPC1## Their N-oxides and acid addition salts thereof are provided which have been found to possess anti-inflammatory activity. In addition, methods for preparing such compounds, pharmaceutical compositions containing such compounds, and methods for using such compositions as anti-inflammatory agents are also provided.

  提供了公式##SPC1##的化合物，它们的N-氧化物和酸加成盐具有抗炎活性。此外，还提供了制备这些化合物的方法，含有这些化合物的药物组合物以及使用这些组合物作为抗炎剂的方法。
• 2-(2,2,2,-Trifluoroet
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04065617A1

  公开（公告）日：1977-12-27

  Antiinflammatory activity is demonstrated by compounds having the formula ##STR1## wherein R.sub.1 is hydrogen, chloro, fluoro, alkyl, alkoxy or trifluoromethyl and R.sub.2 is hydrogen, alkyl, arylalkyl, hydroxyalkyl, or carboximidamide, or pharmaceutically acceptable salts thereof.

  具有以下式子的化合物表现出抗炎活性：##STR1## 其中 R.sub.1 为氢、氯、氟、烷基、烷氧基或三氟甲基，R.sub.2 为氢、烷基、芳基烷基、羟基烷基或羧酸亚胺基，或其药学上可接受的盐。
• 2-Amino-8-arylideno-3,4,5,6,7,8-hexahydro-4-arlypyrido[4,3-d]pyrimidines
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04085102A1

  公开（公告）日：1978-04-18

  Compounds of the formula ##STR1## and the pharmaceutically acceptable acid-addition salts thereof wherein R.sup.1 and R.sup.2 are hydrogen or alkyl of 1 to 4 carbons; R is hydrogen, alkyl of 1 to 4 carbons, alkanoyl of 2 to 5 carbons, or ##STR2## WHEREIN N IS 1, 2, OR 3; R.sup.3 is ##STR3## and X and X.sup.1 are hydrogen, halogen, alkyl of 1 to 4 carbons, alkoxy of 1 to 4 carbons, or trifluoromethyl are disclosed. These compounds are useful as central nervous system depressants and in particular as muscle relaxants.

  本发明涉及式##STR1##化合物及其药学上可接受的酸加合物盐，其中R.sup.1和R.sup.2为氢或1至4碳的烷基；R为氢、1至4碳的烷基、2至5碳的酰基烷基，或##STR2##其中N为1、2或3；R.sup.3为##STR3##，X和X.sup.1为氢、卤素、1至4碳的烷基、1至4碳的烷氧基或三氟甲基。这些化合物可用作中枢神经系统抑制剂，特别是作为肌肉松弛剂。
• Ruzicka; Fornasir, Helvetica Chimica Acta, 1920, vol. 3, p. 812
  作者：Ruzicka、Fornasir

  DOI：——

  日期：——
• CLEFMA—An anti-proliferative curcuminoid from structure–activity relationship studies on 3,5-bis(benzylidene)-4-piperidones
  作者：Pallavi Lagisetty、Prachi Vilekar、Kaustuv Sahoo、Shrikant Anant、Vibhudutta Awasthi

  DOI：10.1016/j.bmc.2010.06.055

  日期：2010.8

  3,5-Bis(benzylidene)-4-piperidones are being advanced as synthetic analogs of curcumin for anti-cancer and anti-inflammatory properties. We performed structure-activity relationship studies, by testing several synthesized 3,5-bis(benzylidene)-4-piperidones for anti-proliferative activity in lung adenocarcinoma H441 cells. Compared to the lead compound 1, or 3,5-bis(2-fluorobenzylidene)-4-piperidone, five compounds were found to be more potent (IC50 <30 mu M), and 16 compounds possessed reduced cell-killing efficacy (IC50 >50 mu M). Based on the observations, we synthesized 4-[3,5-bis(2-chlorobenzyl-idene-4-oxo-piperidine-1-yl)-4-oxo-2-butenoic acid] (29 or CLEFMA) as a novel analog of 1. CLEFMA was evaluated for anti-proliferative activity in H441 cells, and was found to be several folds more potent than compound 1. We did not find apoptotic cell population in flow cytometry, and the absence of apoptosis was confirmed by the lack of caspase cleavage. The electron microscopy of H441cells indicated that CLEFMA and compound 1 induce autophagic cell death that was inhibited by specific autophagy inhibitor 3-methyladenine. The results suggest that the potent and novel curcuminoid, CLEFMA, offers an alternative mode of cell death in apoptosis-resistant cancers. (C) 2010 Elsevier Ltd. All rights reserved.