(E)-4-((3-ethyl-2,4,4-trimethylcyclohex-2-enylidene)methyl)benzoic acid | 1047683-69-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-4-((3-ethyl-2,4,4-trimethylcyclohex-2-enylidene)methyl)benzoic acid
• 英文别名: (E)-4-(3-ethyl-2,4,4-trimethylcyclohex-2-enylidenemethyl)benzoic acid；4-[(E)-(3-ethyl-2,4,4-trimethylcyclohex-2-en-1-ylidene)methyl]benzoic acid
• CAS: 1047683-69-1
• 化学式: C₁₉H₂₄O₂
• 分子量: 284.398
• InChiKey: ZCBZETDCCXLBGJ-FOWTUZBSSA-N

物化性质

• 熔点：
  187 °C(Solv: ethanol (64-17-5))
• 沸点：
  429.3±24.0 °C(Predicted)
• 密度：
  1.045±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-4-((3-ethyl-2,4,4-trimethylcyclohex-2-enylidene)methyl)benzoic acid 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 5-[4-[(E)-(3-ethyl-2,4,4-trimethylcyclohex-2-en-1-ylidene)methyl]phenyl]-3-(4-fluorophenyl)-1,2,4-oxadiazole
  参考文献：
  名称：

  Design and synthesis of 3,5-disubstituted 1,2,4-oxadiazole containing retinoids from a retinoic acid receptor agonist

  摘要：

  We previously synthesized novel retinoid libraries, and after screening for bioactivity found one compound BT10 that functions as a specific agonist for retinoic acid receptors. This lead compound was further derivatized using SAR and LRD to obtain 3,5-disubstituted-1,2,4-oxadiazole-containing retinoids. The new oxadiazole (amide bioisosters)-containing retinoids (compounds 1, 2, 3, 4, 5, and 6) were synthesized in 42-65% yield by reacting with (E)-4-((3-ethy1,2-4,4,4-trimethylcyclohex-2-enylidene)methyl)benzoic acid and phenyl substituted amidoxime in DMF using CDI as the coupling reagent. The biological activities of the synthesized compounds are currently being evaluated. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.03.011
• 作为产物：
  描述：

  (E)-Methyl 4-((3-Ethyl-2,4,4-trimethylcyclohex-2-en-1-ylidene)methyl)benzoate 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 以87%的产率得到(E)-4-((3-ethyl-2,4,4-trimethylcyclohex-2-enylidene)methyl)benzoic acid
  参考文献：
  名称：

  Design and synthesis of (E)-4-((3-ethyl-2,4,4-trimethylcyclohex-2-enylidene)methyl)benzoic acid

  摘要：

  顺式-4-((3-乙基-2、4、4-三甲基环己二烯基甲基)的苯酸，编号为 6，从β-环丙醇 1 开始，产率 87% 得到。目标化合物 6 从化合物 1 经过 Grignard 反应生成醇 2。化合物 2 被转化为 Wittig 盐 3，使用甲醇 4 与 butyllithium 和 hexane，在 -78℃ 时反应生成酸酐 5。酸酐 5 被水解，随后经过酸化处理，最终获得了产物 6，编号为白色固体，产率 87%。发表于 Elsevier 出版社。

  DOI：

  10.1016/j.tetlet.2008.05.136

文献信息

• Design, synthesis of novel peptidomimetic derivatives of 4-HPR for rhabdoid tumors
  作者：Bhaskar C. Das、Melissa E. Smith、Ganjam V. Kalpana

  DOI：10.1016/j.bmcl.2008.05.097

  日期：2008.7

  survival. 4-HPR, a synthetic retinoid that down-modulates Cyclin D1, has shown promise in treating various tumors including RTs. In this study, we have generated a chemical library of peptidomimetic derivatives of 4-HPR in an attempt to create a more biologically active compound for use as a therapeutic agent against RTs and other tumors. We have synthesized novel peptidomimetic compound by substituting

  横纹肌瘤（RTs）是一种极具侵略性的儿科恶性肿瘤，其起因是INI1 / hSNF5肿瘤抑制基因的缺失。INI1的丢失导致细胞周期蛋白D1的异常表达，这支持横纹肌瘤的发生和生存。4-HPR是一种下调Cyclin D1的合成类维生素A，在治疗包括RTs在内的多种肿瘤中显示出了希望。在这项研究中，我们已经建立了4-HPR拟肽衍生物的化学文库，以试图创建一种更具生物活性的化合物，用作对抗RTs和其他肿瘤的治疗剂。我们已经合成了新型拟肽化合物，该化合物通过用环结构取代烯烃骨架而保留了横纹肌瘤细胞培养模型中的生物活性。我们进一步鉴定了拟肽化合物的衍生物（11d，基于针对横纹肌瘤细胞的生存分析，IC（50）约为3 microM，效力是4-HPR（1，IC（50）约为15 microM）约五倍。这些研究表明，保留细胞毒活性的拟肽衍生物是有前景的针对RTs和其他肿瘤的新型化学治疗剂。
• Design and synthesis of (E)-4-((3-ethyl-2,4,4-trimethylcyclohex-2-enylidene)methyl)benzoic acid
  作者：Bhaskar C. Das、George W. Kabalka

  DOI：10.1016/j.tetlet.2008.05.136

  日期：2008.8

  (E)-4-((3-Ethyl-2,4,4-trimethylcyclohex-2-enylidene)methyl)benzoic acid, 6, was synthesized in 87% starting from beta-cyclocitral. The target compound 6 was synthesized starting from 1 via a Grignard reaction to form alcohol 2. Compound 2 was converted to Wittig salt 3 by treatment with aldehyde 4 in butyllithium and hexane at -78 degrees C to form ester 5. Ester 5 was saponified and, following acidification, acid 6 was isolated as white solid yield 87%. Published by Elsevier Ltd.

  顺式-4-((3-乙基-2、4、4-三甲基环己二烯基甲基)的苯酸，编号为 6，从β-环丙醇 1 开始，产率 87% 得到。目标化合物 6 从化合物 1 经过 Grignard 反应生成醇 2。化合物 2 被转化为 Wittig 盐 3，使用甲醇 4 与 butyllithium 和 hexane，在 -78℃ 时反应生成酸酐 5。酸酐 5 被水解，随后经过酸化处理，最终获得了产物 6，编号为白色固体，产率 87%。发表于 Elsevier 出版社。
• FENRETINIDE DERIVATIVES AND USES THEREOF AS THERAPEUTIC, DIAGNOSTIC AND IMAGING AGENTS
  申请人：Kalpana Ganjam V.

  公开号：US20110091383A1

  公开（公告）日：2011-04-21

  Synthetic peptidomimetic derivatives and phenyl group derivatives of Fenretinide (4-HPR) are disclosed, as are their uses as therapeutic, diagnostic and imaging agents for cancer and other diseases.

  本发明涉及Fenretinide（4-HPR）的合成肽类模拟衍生物和苯基衍生物，以及它们作为治疗、诊断和肿瘤及其他疾病成像剂的用途。
• <i>N</i>-Carbamidoyl-4-((3-ethyl-2,4,4-trimethylcyclohexyl)methyl)benzamide Enhances Staurosporine Cytotoxic Effects Likely Inhibiting the Protective Action of Magmas toward Cell Apoptosis
  作者：Maria Chiara Zatelli、Teresa Gagliano、Michela Pelà、Sara Bianco、Valerio Bertolasi、Federico Tagliati、Remo Guerrini、Ettore degli Uberti、Severo Salvadori、Claudio Trapella

  DOI：10.1021/jm5000535

  日期：2014.6.12

  We recently demonstrated that Magmas overexpression protects GH-secreting rat pitutitary adenoma cell lines from apoptosis by inhibiting cytochrome c release from mitochondria after treatment with staurosporine, strongly suggesting a role of Magmas in preventing apoptosis. The aim of this study was to produce a drug that, by inhibiting Tim16, may sensitize chemoresistant tumor cell to proapoptotic stimuli. We synthesized six compounds and challenged their sensitizing effects toward the proapoptotic effects of staurosporine in the TT cell line, derived from a human medullary thyroid carcinoma. We found that compound 5, devoid of the planarity in the aliphatic part of the lead 1, is not cytotoxic but enhances the proapoptotic effects of staurosporine by reducing MMP activation. Compound 5 may be useful for cancer treatment in association with chemotherapeutic drugs, possibly allowing a reduction of the chemotherapeutic agent effective dose.
• Identification of new hit to lead magmas inhibitors as potential therapeutics for glioblastoma
  作者：Bhaskar C. Das、Javier J. Lepe、Mohammed Adil Shareef、Naomi Lomeli、Sasmita Das、Daniela A. Bota

  DOI：10.1016/j.bmcl.2023.129330

  日期：2023.7