(E)-1-(pyridin-4-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-1-(pyridin-4-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• 英文别名: 1-(pyridin-4-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one；1-pyridin-4-yl-3-(3,4,5-trimethoxyphenyl)propenone；(E)-3-(3,4,5-trimethoxyphenyl)-1-(pyridin-4-yl)prop-2-en-1-one；CYP1A1 inhibitor 8a；(E)-1-pyridin-4-yl-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• 化学式: C₁₇H₁₇NO₄
• 分子量: 299.326
• InChiKey: LTMMHRRDZVGAIL-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  57.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  piperidine-1-carboxamidine hydrochloride 、 (E)-1-(pyridin-4-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one 在 sodium isopropylate 作用下， 以 异丙醇 为溶剂， 反应 8.0h， 以67%的产率得到
  参考文献：
  名称：

  Synthesis of 2,4,6-trisubstituted pyrimidines as antimalarial agents

  摘要：

  A series of 2,4,6-trisubstituted-pyrimidines were synthesized and evaluated for their in vitro antimalarial activity against Plasmodium falciparum. Of the 18 compounds synthesized, 14 compounds have shown MIC in the range of 0.25-2 mu g/mL. These compounds are in vitro severalfold more active than pyrimethamine. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.061
• 作为产物：
  描述：

  4-乙酰吡啶 、 3,4,5-三甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 (E)-1-(pyridin-4-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  抗疟疾活性和新的三取代嘧啶的合成。

  摘要：

  合成了一系列的2,4,6-三取代-嘧啶并评估了它们对恶性疟原虫的体外抗疟活性。在合成的30种化合物中，有21种化合物的MIC在0.5-2 microg / mL范围内。这些化合物在体外的活性是乙胺嘧啶的几倍。

  DOI：

  10.1016/j.bmcl.2005.04.014

文献信息

• Synthesis of 2,4,6-trisubstituted pyrimidine and triazine heterocycles as antileishmanial agents
  作者：Naresh Sunduru、Anu Agarwal、Sanjay Babu Katiyar、Nishi、Neena Goyal、Suman Gupta、Prem M.S. Chauhan

  DOI：10.1016/j.bmc.2006.08.009

  日期：2006.12

  A series of 2,4,6 trisubstituted pyrimidines and triazines have been synthesized and screened for its in vitro antileishmanial activity profile in promastigote model. Nine compounds have shown > 94% inhibition against promastigotes at a concentration of 10 mu g/mL. (c) 2006 Elsevier Ltd. All rights reserved.
• Antimalarial activity of 2,4,6-trisubstituted pyrimidines
  作者：Anu Agarwal、Kumkum Srivastava、S.K. Puri、Prem M.S. Chauhan

  DOI：10.1016/j.bmcl.2005.02.015

  日期：2005.4

  A series of 2,4,6-trisubstituted pyrimidines (3a-o) was synthesized and evaluated for their in vitro antimalarial activity against P. falciparum. Out of the 15 compounds synthesized 11 compounds showed MIC in the range of 0.5-2 mu g/mL. These compounds are in vitro several folds more active than pyrimethamine. (c) 2005 Elsevier Ltd. All rights reserved.
• ( E )-3-(3,4,5-Trimethoxyphenyl)-1-(pyridin-4-yl)prop-2-en-1-one, a heterocyclic chalcone is a potent and selective CYP1A1 inhibitor and cancer chemopreventive agent
  作者：Neill J. Horley、Kenneth J.M. Beresford、Supriya Kaduskar、Prashant Joshi、Glen J.P. McCann、Ketan C. Ruparelia、Ibidapo S. Williams、Linda Gatchie、Vinay R. Sonawane、Sandip B. Bharate、Bhabatosh Chaudhuri

  DOI：10.1016/j.bmcl.2017.11.009

  日期：2017.12

  The overexpression of CYP1 family of enzymes is reported to be associated with development of human carcinomas. It has been well reported that CYP1A1 specific inhibitors prevents carcinogenesis. Herein, thirteen pyridine-4-yl series of chalcones were synthesized and screened for inhibition of CYP1 isoforms 1A1, 1B1 and 1A2 in Sacchrosomes (TM) and live human HEK293 cells. The structure-activity relationship analysis indicated that chalcones bearing tri-alkoxy groups (8a and 8k) on non-heterocyclic ring displayed selective inhibition of CYP1A1 enzyme, with IC50 values of 58 and 65 nM, respectively. The 3,4,5-trimethoxy substituted derivative 8a have shown > 10-fold selectivity towards CYP1A1 with respect to other enzymes of the CYP1 sub-family and > 100-fold selectivity with respect to CYP2 and CYP3 family of enzymes. The potent and selective CYP1A1 inhibitor 8a displayed antagonism of B[a] P mediated activation of aromatic hydrocarbon receptor (AhR) in yeast cells, and also protected human cells from CYP1A1-mediated B[a] P toxicity in human cells. This potent and selective inhibitor of CYP1A1 enzyme have a potential for development as cancer chemopreventive agent. (C) 2017 Elsevier Ltd. All rights reserved.
• [EN] COMPOUND<br/>[FR] COMPOSÉ
  申请人：UNIV MONTFORT

  公开号：WO2015166040A2

  公开（公告）日：2015-11-05

  The present application relates to a compound of formula (I) for use in the prevention or treatment of cancer, wherein rings A and B are independently an aryl or a heteroaryl, wherein the aryl and/or the heteroaryl are optionally substituted with one or more substitutents selected from the group consisting of aliphatic, alkoxy, thioalkyl, alkylamino, halogen, hydroxy, cyano, nitro, hydroxyalkyl, alkylcarbonyloxy, alkoxycarbonyl, alkylcarbonyl, haloalkyl, alkylsulfonylamino NH2, NO2, SO2RX, SORX and COORX, where RX is hydrogen, aliphatic or aryl. The compounds are particularly provided for the prevention and/or treatment of cancer of the lung, colon, pancreas, liver and/or kidney.