(1E,4E)-1-(3-chlorophenyl)-5-(2,6,6-trimethylcyclohex-1-enyl)penta-1,4-dien-3-one | 1204518-01-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1E,4E)-1-(3-chlorophenyl)-5-(2,6,6-trimethylcyclohex-1-enyl)penta-1,4-dien-3-one
• 英文别名: (1E,4E)-1-(3-chlorophenyl)-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-1,4-dien-3-one；(1E,4E)-1-(3-chlorophenyl)-5-(2,6,6-trimethylcyclohexen-1-yl)penta-1,4-dien-3-one
• CAS: 1204518-01-3
• 化学式: C₂₀H₂₃ClO
• 分子量: 314.855
• InChiKey: LIHTVOYUNDGJEH-HULFFUFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1E,4E)-1-(3-chlorophenyl)-5-(2,6,6-trimethylcyclohex-1-enyl)penta-1,4-dien-3-one 、 苯肼 以 乙醇 为溶剂， 反应 8.0h， 以62%的产率得到3-(3-chlorophenyl)-2-phenyl-5-[(E)-2-(2,6,6-trimethylcyclohexen-1-yl)ethenyl]-3,4-dihydropyrazole
  参考文献：
  名称：

  Chemotherapy of leishmaniasis part X: Synthesis and bioevaluation of novel terpenyl heterocycles

  摘要：

  Some novel alpha and beta ionone based chalcones and their dihydropyrazolidines/pyrazolidines have been synthesized and evaluated for their in vitro and in vivo antileishmanial activities against Leishmania donovani. Amongest all, one compound (4d) exhibited significant in vitro activity against intracellular amastigotes of Leishmania donovani with IC50 values of 7.49 mu M and was found promising as compared to reference drug, miltefosine. On the basis of good Selectivity Index (S.I.), the compound was further tested for its in vivo response against Leishmania donovani/hamster model and has shown significant inhibition of parasite multiplication (81%). The present study has helped us in identifying a new lead that could be exploited as a potential antileishmanial agent. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.110
• 作为产物：
  描述：

  beta-紫罗酮 、 3-氯苯甲醛 在 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 1.5h， 生成 (1E,4E)-1-(3-chlorophenyl)-5-(2,6,6-trimethylcyclohex-1-enyl)penta-1,4-dien-3-one
  参考文献：
  名称：

  新的类萜样比沙可康†的细胞毒性活性的分子模型

  摘要：

  这项研究描述了（1 E，4 E）-1-（3-氯苯基）-5-（2,6,6-三甲基环己-1-烯-1-基）戊-1,4-二烯的合成和结构-3-one（BC I）。X射线单晶衍射和Hirshfeld表面分析描述了超分子排列和拓扑分析。在B3LYP / 6-311 ++ G（d，p）的理论水平上进行了理论计算，例如QTAIM，前沿分子轨道，MEP和红外光谱分配。此外，这项工作评估了针对DNA的分子对接（PDB ID：1BNA）和针对两种肿瘤细胞系的细胞毒活性。BC I分子具有环己烯环的半椅构象，超分子排列由C 6 -H 6稳定。1O 1和C 7 -H 7 ⋯O 1相互作用。MEP和对接分析表明可能在羰基上发生亲电子攻击。

  DOI：

  10.1039/c9nj03452h

文献信息

• Chemotherapy of leishmaniasis part X: Synthesis and bioevaluation of novel terpenyl heterocycles
  作者：Avinash Tiwari、Santosh Kumar、S.N. Suryawanshi、Monika Mittal、Preeti Vishwakarma、Suman Gupta

  DOI：10.1016/j.bmcl.2012.10.110

  日期：2013.1

  Some novel alpha and beta ionone based chalcones and their dihydropyrazolidines/pyrazolidines have been synthesized and evaluated for their in vitro and in vivo antileishmanial activities against Leishmania donovani. Amongest all, one compound (4d) exhibited significant in vitro activity against intracellular amastigotes of Leishmania donovani with IC50 values of 7.49 mu M and was found promising as compared to reference drug, miltefosine. On the basis of good Selectivity Index (S.I.), the compound was further tested for its in vivo response against Leishmania donovani/hamster model and has shown significant inhibition of parasite multiplication (81%). The present study has helped us in identifying a new lead that could be exploited as a potential antileishmanial agent. (c) 2012 Elsevier Ltd. All rights reserved.
• Molecular modeling of cytotoxic activity of a new terpenoid-like bischalcone
  作者：Lóide O. Sallum、Vera L. Siqueira、Jean M. F. Custodio、Nádia M. Borges、Aliny P. Lima、Davi C. Abreu、Elisângela de P. S. Lacerda、Rosa S. Lima、Alisson M. de Oliveira、Ademir J. Camargo、Hamilton B. Napolitano

  DOI：10.1039/c9nj03452h

  日期：——

  B3LYP/6-311++G(d,p) level of theory. Also, this work evaluates molecular docking against DNA (PDB ID: 1BNA) and cytotoxic activity against two tumor cell lines. The BC I molecule has a half chair conformation of the cyclohexene ring, and the supramolecular arrangements are stabilized by C6–H6⋯O1 and C7–H7⋯O1 interactions. MEP and docking analyses indicate an electrophilic attack that is likely to occur

  这项研究描述了（1 E，4 E）-1-（3-氯苯基）-5-（2,6,6-三甲基环己-1-烯-1-基）戊-1,4-二烯的合成和结构-3-one（BC I）。X射线单晶衍射和Hirshfeld表面分析描述了超分子排列和拓扑分析。在B3LYP / 6-311 ++ G（d，p）的理论水平上进行了理论计算，例如QTAIM，前沿分子轨道，MEP和红外光谱分配。此外，这项工作评估了针对DNA的分子对接（PDB ID：1BNA）和针对两种肿瘤细胞系的细胞毒活性。BC I分子具有环己烯环的半椅构象，超分子排列由C 6 -H 6稳定。1O 1和C 7 -H 7 ⋯O 1相互作用。MEP和对接分析表明可能在羰基上发生亲电子攻击。