(2E,6E)-2,6-双((5-甲基噻吩-2-基)亚甲基)环己酮 | 1018785-87-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: (2E,6E)-2,6-双((5-甲基噻吩-2-基)亚甲基)环己酮
• 英文名称: (2E,6E)-2,6-bis((5-methylthiophen-2-yl)methylene)cyclohexanone
• 英文别名: (2E,6E)-2,6-Bis[(5-methylthiophen-2-yl)methylene]cyclohexanone；(2E,6E)-2,6-bis[(5-methylthiophen-2-yl)methylidene]cyclohexan-1-one
• CAS: 1018785-87-9
• 化学式: C₁₈H₁₈OS₂
• 分子量: 314.472
• InChiKey: CBTLOJPWSRXZDD-WFYKWJGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  73.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2E,6E)-2,6-双((5-甲基噻吩-2-基)亚甲基)环己酮 、 肌氨酸 、 1-(吗啉基甲基)-1H-吲哚-2,3-二酮 以 乙醇 为溶剂， 反应 22.0h， 以58%的产率得到1'-methyl-4'-(5-methyl-2-furanyl)-3-[(5-methyl-2-furanyl)methylidene]-1"-[(4-morpholinyl)methylene]-dispiro[cyclohexane-1,3'-pyrrolidine-2',3"-[3H]indole]-2,2"(1"H)-dione
  参考文献：
  名称：

  Design, synthesis and QSAR studies of dispiroindole derivatives as new antiproliferative agents

  摘要：

  A variety of 4'-ary1-3-(arylmethylidene)-1 ''-[(cyclic-amino)methylene]-1'-methyl-dispiro[cyclohexane-1,3'-pyrrolidine-2',3 ''-[3H]indole]-2,2 ''(1"H)-diones 4a-u were prepared via reaction of 2E,6E-bis(arylidene)-1-cyclohexanones 1a-i with azomethine ylides, generated in situ via a decarboxylative condensation of isatins 2a-c and sarcosine (3). Single crystal X-ray study of 4a, revealed structural and stereochemical features of these derivatives. While most of the synthesized compounds exhibit mild antitumor properties when tested against various human tumor cell lines (HEPG2 "liver", HELA "cervical" and PD "prostate" cancers), three of them, 4d and 4p (active against HEPG2), and compound 4g (active against HELA), demonstrated higher activities, that were close or even higher than that of the reference standard Doxorubicin. QSAR studies revealed good predictive and statistically significant 3 descriptor models (r(2) = 0.903-0.812, r(adjusted)(2) = 0.855-0.672, r(prediction)(2) = 0.773-0.605). (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.07.035
• 作为产物：
  描述：

  5-甲基-2-噻吩甲醛 、 环己酮 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 (2E,6E)-2,6-双((5-甲基噻吩-2-基)亚甲基)环己酮
  参考文献：
  名称：

  Synthesis and anti-inflammatory activities of mono-carbonyl analogues of curcumin

  摘要：

  Curcumin has been extensively studied for its anti-inflammatory activities. However, its potential beneficial effects on various disease preventions and treatments are limited by its unstable structure. The beta-diketone moiety renders curcumin to be rapidly metabolized by aldo -keto reductase in liver. In the present study, a series of curcumin analogues with more stable chemical structures were synthesized and several compounds showed an enhanced ability to inhibit lipopolysaccharide ( LPS)-induced TNF-alpha and IL-6 synthesis in macrophages. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.12.068

文献信息

• Exploration and synthesis of curcumin analogues with improved structural stability both in vitro and in vivo as cytotoxic agents
  作者：Guang Liang、Lili Shao、Yi Wang、Chengguang Zhao、Yanhui Chu、Jian Xiao、Yu Zhao、Xiaokun Li、Shulin Yang

  DOI：10.1016/j.bmc.2008.10.044

  日期：2009.3

  Curcumin has a surprisingly wide range of chemo-preventive and chemo-therapeutic activities and is under investigation for the treatment of various human cancers. However, the clinical application of curcumin has been significantly limited by its instability and poor metabolic property. Although a number of synthetic modi. cations of curcumin have been studied intensively in order to develop a molecule with enhanced bioactivities, few synthetic studies were done for the improvement of pharmacokinetic profiles. In the present study, a series of mono-carbonyl analogues of curcumin were designed and synthesized by deleting the reactive beta-diketone moiety, which was considered to be responsible for the pharmacokinetic limitation of curcumin. The results of the in vitro stability studies and in vivo pharmacokinetic studies indicated that the stability of these mono-carbonyl analogues was greatly enhanced in vitro and their pharmacokinetic profiles were also significantly improved in vivo. Furthermore, the cytotoxic activities of mono-carbonyl analogues were evaluated in seven different tumor cell lines by MTT assay and the structure-activity relation (SAR) was discussed and concluded. The results suggest that the five-carbon linker-containing analogues of curcumin may be favorable for the curcumin-based drug development both pharmacokinetically and pharmacologically. (C) 2009 Published by Elsevier Ltd.