ethoxycarbonyl (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoate | 134394-00-6

• 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: ethoxycarbonyl (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoate
• CAS: 134394-00-6
• 化学式: C₂₃H₃₂O₄
• 分子量: 372.505
• InChiKey: COYJALDQLMQQMB-NBIQJRODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.22
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethoxycarbonyl (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoate 在 Amberlyst 15 ion-exchange resin 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 N-hydroxyretinamide
  参考文献：
  名称：

  组蛋白乙酰转移酶活性的小分子抑制剂：鉴定和生物学特性。

  摘要：

  从对21种化合物进行的酵母表型筛选开始，我们描述了两个小分子（9和18）的鉴定，这些小分子能够显着降低酿酒酵母细胞的生长，从而模拟GCN5缺失突变体的作用。经过GCN5依赖性基因转录检测的测试，化合物9和18的报告基因活性大大降低。在酿酒酵母组蛋白H3末端尾部测定中，用0.6-1 mM 9处理可大大降低H3乙酰化水平，而18仅在1.5 mM时有效。在人类白血病U937细胞系中，在1 mM时9和18表现出对细胞周期（G1期阻滞，9），凋亡（9）和粒细胞分化（18）的影响。当对U937细胞核提取物进行测试以评估其组蛋白乙酰转移酶（HAT）的抑制作用时，当以500 microM使用时，这两种化合物都能够降低酶的活性。合成了另一种喹啉化合物22，目的是提高在9和18中观察到的活性。在HAT分析中进行测试，22在50和25 microM时能够降低HAT的催化作用，因此可与熊果酸姜黄素相提并论。 ，并

  DOI：

  10.1021/jm060601m
• 作为产物：
  描述：

  (6R,7R)-3-[(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoyloxymethyl]-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 在 吡啶 、 β-lactamase from Staphylococcus aureus 95 、 deuterated phosphate buffer 作用下， 以 氘代二甲亚砜 、 二氯甲烷 为溶剂， 反应 0.17h， 生成 ethoxycarbonyl (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoate
  参考文献：
  名称：

  Design and synthesis of a cephalosporin-retinoic acid prodrug activated by a monoclonal antibody–β-lactamase conjugate

  摘要：

  Two novel series of all-trans-beta -retinoic acid derivatives were synthesized and found to possess anticancer activity. The first series, cephalosporin 3 ' -retinoic esters 6 and 7 were, respectively, obtained by the condensation of all-trans-beta -retinoic acid (2) with cephalosporins 4 and 5. The second series, 7-(retinamido)cephalosporins 11 and 12, were synthesized, respectively, by the condensation of 2 with cephalosporins 9 and 10. These four heretofore undescribed compounds 6, 7, 11, and 12 showed inhibitory activity against murine leukemias (L1210 and P388), sarcoma 180, breast carcinoma (MCF7), and human T-lymphocytes (Molt4/C8 and CEM/0). They also inhibited squamous metaplasia and keratinization in tracheal or.-an cultures derived from vitamin-A-deficient hamsters. Moreover, cephalosporin 3 ' -retinoic ester 7 exhibited enhanced activity against keratinization with ED50 = 3.91 x 10(-11) M in the presence of a beta -lactamase from Staphylococcus aureus 95. A tumor targeting fusion protein (dsFv3-beta -lactamase) was also used in conjunction with cephem-based retinoid 7 and the potency of 7 toward L1210, P388, and MCF7 was found to approach that of the free retinoic acid (2). In the presence of dsFv3-beta -lactamase, tumor cells were found to be much more susceptible to retinoid 7 than normal human embryonic lung cells. These notions provide a new approach to the use of beta -retinoic acid for antitumor therapy. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00127-4

文献信息

• Syntheses of Novel Isopenam and Isocephem Antibiotics. Preparation of a retinamido derivative of a highly strained ?-lactam as potent anticancer agent
  作者：Gholam H. Hakimelahi、Min-Jen Shiao、Jih Ru Hwu、Hady Davari

  DOI：10.1002/hlca.19920750610

  日期：1992.10.2

  Syntheses of the cis-configurated isopenam 9 (Scheme 1), isocephem 14 (Scheme 2), and isocephem 19 (Scheme 3) are described. The key step in the preparation of 14 and 19 involved a Pummerer-type rearrangement of the corresponding sulfoxides 12 and 18. These β-lactams were found to possess biological activity against several pathogenic microorganisms in vitro. The electronic activation of the lactam

  描述了顺式构型的异戊烷9（方案1），异头孢烯14（方案2）和异头孢烯19（方案3）的合成。制备14和19的关键步骤涉及相应亚砜12和18的Pummerer型重排。发现这些β-内酰胺在体外对几种病原微生物具有生物活性。19的内酰胺部分的电子活化显着增强其生物学活性。视黄酸部分通过氨基接头连接至19。所得的视网膜酰胺基-β-内酰胺21在由缺乏维生素A的仓鼠获得的气管器官培养物中显示出显着的细胞抑制活性。
• [EN] ESTERS OF A RETINOID AND TOCOPHEROL OR TERT-BUTYLHYDROQUINONE AND PREPARATIONS THEREOF<br/>[FR] ESTERS D'UN RÉTINOÏDE ET DE TOCOPHÉROL OU DE TERT-BUTYLHYDROQUINONE ET LEURS PRÉPARATIONS
  申请人：[en]CONAGEN INC.

  公开号：WO2023023044A1

  公开（公告）日：2023-02-23

  The present disclosure provides esters of a retinoid and an alcohol selected from the group consisting of tocopherols and tert-butyl hydroquinone, such as esters of Formula (I). The present disclosure also provides compositions and kits comprising the esters, methods of producing the esters, and methods of using the esters (e.g., for treating or preventing a skin disease, slowing the ageing of the skin, improving the appearance of the skin, or modulating a retinoid receptor).