α,α'-bis(thiophen-3-ylmethylene)cyclohexanone | 101109-88-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: α,α'-bis(thiophen-3-ylmethylene)cyclohexanone
• 英文别名: 2,6-bis(3-thienylidene)cyclohexanone；2,6-Bis(thiophen-3-ylmethylidene)cyclohexan-1-one
• CAS: 101109-88-0
• 化学式: C₁₆H₁₄OS₂
• mdl: MFCD01306194
• 分子量: 286.419
• InChiKey: BVEGPXVJSTZUMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.03
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1,3-二甲基-6-氨基脲嘧啶 、 α,α'-bis(thiophen-3-ylmethylene)cyclohexanone 在 苄基三甲基氢氧化铵 作用下， 以 四氢呋喃 为溶剂， 生成 (E)-1,3-dimethyl-5-(thiophen-3-yl)-9-(thiophen-3-ylmethylene)-6,7,8,9-tetrahydropyrimido[4,5-b]quinoline-2,4(1H 3 H)-dione
  参考文献：
  名称：

  The products of the reaction between 6-amine-1,3-dimethyl uracil and bis-chalcones induce cytotoxicity with massive vacuolation in HeLa cervical cancer cell line

  摘要：

  As a part of our research in the chemistry of chalcones we have prepared four pyrimidine monoadducts of bis-chalcones through the reaction with 6-amino-1,3-dimethyl uracil. These compounds displayed cytotoxicity with a massive vacuolation in different human cell lines in vitro. Compound 6 was the most cytotoxic inducer of vacuoles, this compound induced G1 phase cell cycle arrest, and their cytotoxicity went without morphological and biochemical evidence of apoptotic cell death in HeLa cells. In addition, our results showed that this vacuole formation does not require de novo protein synthesis and the content vacuolar is acidic. Compound 6 induce necrotic cell death with excessive vacuolation, similar to a process of autophagy. Spautin-1 an inhibitor of autophagy, decreased the transformation of microtubule-associated protein 1 light chain 3 (LC3B-I) to LC3B-II and the vacuolation induced by compound 6 in HeLa cells, both autophagy processes. These compounds could be of pivotal importance in the study of non-apoptotic cell death with vacuole formation and could be useful in research into new autophagy inhibitors agents. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.12.021
• 作为产物：
  描述：

  3-噻吩甲醛 、 环己酮 在 Ti₂Cl₂(OPrⁱ)₆*2HOPrⁱ 作用下， 以 甲苯 为溶剂， 反应 13.0h， 以90.3%的产率得到α,α'-bis(thiophen-3-ylmethylene)cyclohexanone
  参考文献：
  名称：

  烷氧基桥连的双核Ti（IV）簇催化的化学选择性Claisen-Schmidt双取代缩合反应

  摘要：

  链烷酮的高效和化学选择性的α，α'-双取代在有机合成中很重要。在本文中，二聚物钛簇Ti 2 Cl 2（OPr i）6 ·2HOPr i（Ti 2）用于克莱森－施密特缩合反应，以选择性活化包含α，α'-亚甲基和高效和化学选择性生产α，α'-双取代链烷酮。高效和化学选择性可以扩展到各种典型的链烷酮和芳族醛。Ti 2的氧桥联二聚体基序 离子Ti-Cl键负责高效和化学选择性。

  DOI：

  10.1016/j.tet.2016.01.055

文献信息

• Synthesis of diarylidenecyclohexanone derivatives as potential anti-inflammatory leads against COX-2/mPGES1 and 5-LOX
  作者：Swayamsiddha Kar、Gayathri Ramamoorthy、Shweta Sinha、Meera Ramanan、Jeevan Kumar Pola、Nageswara Rao Golakoti、Jagadeesh Babu Nanubolu、Suraj Kumar Sahoo、Rajesh Babu Dandamudi、Mukesh Doble

  DOI：10.1039/c9nj00726a

  日期：——

  This study establishes the diarylidenecyclohexanones as good anti-inflammatory pharmacophores with selective high potency against PGE₂and 5-LOX without toxicity towards healthy human cells.

  这项研究将二芳基环己酮作为良好的抗炎药物基团，具有选择性高效抑制PGE₂和5-LOX，且对健康人类细胞无毒性。
• Synthesis, mechanistic and synergy studies of diarylidenecyclohexanone derivatives as new antiplasmodial pharmacophores
  作者：Bishnu P. Joshi、Dinesh Mohanakrishnan、Garima Mittal、Swayamsiddha Kar、Jeevan Kumar Pola、Nageswara Rao Golakoti、Jagadeesh Babu Nanubolu、Rajesh Babu D.、Sai Suraj Kumar S.、Dinkar Sahal

  DOI：10.1007/s00044-018-2237-2

  日期：2018.10

  strains P. falciparum Dd2, IC50 1 µM (Ib) and 2.7 µM (Id)} and PfINDO IC50 1.1 µM (Ib) and 2.5 µM (Id)}. Drug exposure followed by drug withdrawal-based stage-specific kill kinetic studies showed that Ib is shizonticidal within 3 h while the earliest killing actions against Trophozoites and Rings were seen at >3 h and >6 h, respectively. Combination studies of the most potent leads viz. Ib and Id showed

  Diarylidenecyclohexanone（DAC）衍生物（IA-I ，IIA-C和IIIa的-B ）的合成，其特征在于并筛选它们在 体外对氯喹的红内期抗疟原虫活性（CQ）的敏感和抗性菌株的恶性疟原虫通过使用SYBR绿色我荧光测定。DAC衍生物的SAR研究显示抗血浆活性的顺序为3-NO 2（Ib，IC 50 0.95 µM）> 3-氯（Id，IC 50 3 µM）> 4-氯（Ie，IC 50 8.5 µM）> 2氯（Ic的，IC 5013 µM）。进一步的Ib和Id对耐CQ菌株恶性疟原虫Dd2，IC 50 1 µM（Ib）和2.7 µM（Id）}和Pf INDO IC 50 1.1 µM（Ib）和2.5 µM（Id）表现出几乎相同的效力}。药物暴露后再进行基于药物戒断的阶段特异性杀灭动力学研究表明，Ib在3 h内呈杆状杀al，而对滋养体和Rings的最早杀伤作用分别在> 3 h和>
• Chemoselective Claisen–Schmidt bis-substitutional condensation catalyzed by an alkoxy-bridged dinuclear Ti(IV) cluster
  作者：Yufei Wu、Jie Hou、Yuliang Liu、Mingfu Zhang、Chen-Ho Tung、Yifeng Wang

  DOI：10.1016/j.tet.2016.01.055

  日期：2016.3

  The highly efficient and chemoselective α,α′-bis-substitution of alkanones is important in organic synthesis. Herein, a dimeric titanium cluster, Ti2Cl2(OPri)6·2HOPri (Ti2), is used in the Claisen–Schmidt condensation reaction, for the selectively activation of symmetrical ketones containing α,α′-methylene groups and production of α,α′-bis-substituted alkanones in high efficiency and chemoselectivity

  链烷酮的高效和化学选择性的α，α'-双取代在有机合成中很重要。在本文中，二聚物钛簇Ti 2 Cl 2（OPr i）6 ·2HOPr i（Ti 2）用于克莱森－施密特缩合反应，以选择性活化包含α，α'-亚甲基和高效和化学选择性生产α，α'-双取代链烷酮。高效和化学选择性可以扩展到各种典型的链烷酮和芳族醛。Ti 2的氧桥联二聚体基序 离子Ti-Cl键负责高效和化学选择性。
• The products of the reaction between 6-amine-1,3-dimethyl uracil and bis-chalcones induce cytotoxicity with massive vacuolation in HeLa cervical cancer cell line
  作者：José D. Solano、Ignacio González-Sánchez、Marco A. Cerbón、Ángel Guzmán、Miguel A. Martínez-Urbina、Miguel A. Vilchis-Reyes、Eduardo C. Martínez-Zuñiga、Cuauhtémoc Alvarado、Angelina Quintero、Eduardo Díaz

  DOI：10.1016/j.ejmech.2012.12.021

  日期：2013.2

  As a part of our research in the chemistry of chalcones we have prepared four pyrimidine monoadducts of bis-chalcones through the reaction with 6-amino-1,3-dimethyl uracil. These compounds displayed cytotoxicity with a massive vacuolation in different human cell lines in vitro. Compound 6 was the most cytotoxic inducer of vacuoles, this compound induced G1 phase cell cycle arrest, and their cytotoxicity went without morphological and biochemical evidence of apoptotic cell death in HeLa cells. In addition, our results showed that this vacuole formation does not require de novo protein synthesis and the content vacuolar is acidic. Compound 6 induce necrotic cell death with excessive vacuolation, similar to a process of autophagy. Spautin-1 an inhibitor of autophagy, decreased the transformation of microtubule-associated protein 1 light chain 3 (LC3B-I) to LC3B-II and the vacuolation induced by compound 6 in HeLa cells, both autophagy processes. These compounds could be of pivotal importance in the study of non-apoptotic cell death with vacuole formation and could be useful in research into new autophagy inhibitors agents. (C) 2012 Elsevier Masson SAS. All rights reserved.