13-demethyl all-trans-retinoic acid | 58508-31-9

• 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: 13-demethyl all-trans-retinoic acid
• 英文别名: (2E,4E,6E,8E)-7-methyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid
• CAS: 58508-31-9
• 化学式: C₁₉H₂₆O₂
• 分子量: 286.414
• InChiKey: JKGJBNBHOCVZCW-NXCNVKDESA-N

物化性质

• 熔点：
  124-125.5 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))
• 沸点：
  452.7±14.0 °C(Predicted)
• 密度：
  1.019±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• 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：

  13-demethyl all-trans-retinoic acid 在 manganese(IV) oxide 、 lithium aluminium tetrahydride 作用下， 生成 all-trans-13-demethylretinal
  参考文献：
  名称：

  Vibrational analysis of all-trans-retinal

  摘要：

  DOI：

  10.1021/ja00384a003
• 作为产物：
  描述：

  ethyl 13-desmethylretinoate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以77%的产率得到13-demethyl all-trans-retinoic acid
  参考文献：
  名称：

  Preparation and biological activity of 13-substituted retinoic acids

  摘要：

  13-Demethyl or 13-substituted all-E- and 9Z-retinoic acids were synthesized using a palladium-catalyzed coupling reaction of enol triflates and tributylstannylolefins. Their biological activities were then measured. The 13-ethyl analogs exhibited approximately one-half of the antiproliferative and differentiation-inducing activity of ATRA in HL-60 cells. In contrast, in the 9Z-derivatives, all analogs, except for the 13-butyl derivatives, showed apoptosis-inducing activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.04.047

文献信息

• Stereoselective Synthesis of Trienoic Acids: Synthesis of Retinoic Acids and Analogues
  作者：Jérôme Thibonnet、Mohamed Abarbri、Jean-Luc Parrain、Alain Duchêne

  DOI：10.1055/s-2006-950201

  日期：2006.9

  Stereoselective construction of conjugated trienoic acids was achieved through two successive Stille reactions, the first step consisting of the coupling of (E)-1,2-bis(tributylstannyl)ethene and tributylstannyl (Z)- or (E)-3-iodoalk-2-enoates. Two different routes were used for the second step: (1) cross-coupling of the stannyldienoic acid reagents and vinyl iodides, or (2) cross-coupling of vinylstannane

  通过两个连续的 Stille 反应实现共轭三烯酸的立体选择性构建，第一步包括 (E)-1,2-双(三丁基甲锡烷基)乙烯和三丁基甲锡烷基 (Z)- 或 (E)-3-iodoalk- 的偶联2-烯酸。第二步使用了两种不同的途径：(1) 甲锡基二烯酸试剂和乙烯基碘化物的交叉偶联，或 (2) 乙烯基锡烷试剂和通过碘脱苯甲酸化生成的 5-碘戊二烯酸三丁基甲锡酯的交叉偶联的亚锡烷基。通过衍生自 β-或 α-紫罗兰酮和番红醛的 Negishi 二烯的亚锡基金属化合成的乙烯基锡烷提供了获得立体定义的视黄酸的途径。还通过 Sonogashira 偶联制备了一些类视黄醇和 yne 类似物。
• Novel Imaging Agents for Fibrosis
  申请人：Chettibi Salah

  公开号：US20080279765A1

  公开（公告）日：2008-11-13

  The present invention provides a novel imaging agent targeting the mannose-6-phosphate (M6P) receptor suitable for the non-invasive visualization of fibrosis. A method for the preparation of the imaging agent is also provided by the invention, as well as a precursor for use in said method. The invention also provides a pharmaceutical composition comprising the imaging agent and a kit for the preparation of the pharmaceutical composition. In a further aspect, use of the imaging agent for in vivo imaging and in the preparation of a medicament for the diagnosis of a condition in which the mannose-6-phosphate receptor is upregulated is provided.

  本发明提供了一种新型的成像剂，针对甘露糖-6-磷酸（M6P）受体，适用于非侵入性可视化纤维化。本发明还提供了一种用于制备成像剂的方法，以及用于该方法的前体。本发明还提供了包括成像剂的药物组合物以及用于制备药物组合物的工具包。在另一个方面，本发明提供了利用成像剂进行体内成像和制备用于诊断甘露糖-6-磷酸受体上调病况的药物的方法。
• Asymmetric Synthesis of C2-Quaternary Indolin-3-ones Enabled by N-Heterocyclic Carbene Catalysis
  作者：Shuaishuai Fang、Shiyi Jin、Rui Ma、Tao Lu、Ding Du

  DOI：10.1021/acs.orglett.9b01823

  日期：2019.7.5

  (NHC)-catalyzed formal [4 + 2] annulation of 2-aryl-3H-indol-3-ones with α,β-unsaturated carboxylic acids bearing γ-H was developed via an in situ activation strategy. The reaction involves the γ-addition of vinyl enolates to the unique cyclic ketimines to afford chiral tricyclic indolin-3-ones with a quaternary carbon center at 2-position. This protocol provides a rapid and enantioselective pathway to

  通过原位活化策略，开发了N-杂环卡宾（NHC）催化的2-芳基-3 H-吲哚-3-酮与带有γ-H的α，β-不饱和羧酸的正式[4 + 2]环化反应。该反应涉及将烯醇乙烯酯γ加成到独特的环状酮亚胺上，以提供在2-位具有季碳中心的手性三环吲哚-3-酮。该协议提供了一种快速和对映选择性的途径，以访问一类在结构上重要的C2-季吲哚-3-酮类化合物，该化合物可能对药物发现有用。
• Novel intermediates for use in retinoid synthesis
  申请人：——

  公开号：US20040132796A1

  公开（公告）日：2004-07-08

  The invention concerns compounds of formula (I) wherein in particular G presents the —N(CH 3 ) 2 —, —N(C 2 H 5 ) 2 -group or N-pyrrolidine: n is an integer equal to 1 or 2: R 1 , R 2 and R 3 independently of one another, represent a hydrogen atom or a methyl group, the successive unsaturated units capable of being moreover identical or different, provided that at least one of the substituents R 1 , R 2 and R 3 is different from H: and Y 1 and Y 2 represent each a —COOCH 3 group or a —COOC 2 H 5 group.

  本发明涉及式 (I) 的化合物，其中 G 特别呈现-N(CH 3 ) 2 -、-N(C 2 H 5 ) 2 -基团或 N-吡咯烷： n 是等于 1 或 2 的整数： R 1 , R 2 和 R 3 分别代表一个氢原子或一个甲基，连续的不饱和单元可以相同或不同，条件是至少有一个取代基 R 1 , R 2 和 R 3 不同于 H 1 和 Y 2 各代表一个 -COOCH 3 基团或-COOC 2 H 5 基团。
• AURELL, M. J.;PARRA, M.;TORTAJADA, A.;GIL, S.;MESTRES, R., TETRAHEDRON LETT., 31,(1990) N0, C. 4791-5794
  作者：AURELL, M. J.、PARRA, M.、TORTAJADA, A.、GIL, S.、MESTRES, R.

  DOI：——

  日期：——