CAS: 5300-03-8; (2E,4E,6Z,8E)-3,7-Dimethyl-9-(2,6,6-Trimethylcyclohex-1-En-1-yl)Nona-2,4,6,8-Tetraenoic Acid

该化合物是维生素A的衍生物,在各种生物过程中,特别是在视觉和细胞差异方面发挥着关键作用,其特点是不饱和的碳氢化合物结构,其中包括一个有助于其生物活动的双重结合系统;该化合物是一种强大的离心酸受体(RARs),它影响基因表达和细胞功能;9-cis-Retinoic酸因其能够调节上皮组织的增长和区别,并参与胚胎发育的调节,它溶于有机溶剂,但水溶性有限;该化合物对光和空气敏感,需要小心处理和储存条件以保持其稳定性;其治疗用途包括皮肤病理学和肿瘤学的潜在用途,特别是在治疗皮肤病和某些癌症方面.

结构式图片

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上下游产品

(2Z,4E,6Z,8E)-3,7-二甲基-9-(2,6,6-三甲基-1-环己烯基)壬-2,4,6,8-四烯酸 9,13-Di-Cis-Retinoic Acid 5352-74-9
维a酸 All-Trans-Retinoic-Acid 302-79-4
异维a酸 13-Cis-Retinoic Acid 4759-48-2
2,4-戊二烯酸,3-甲基-5-(2,6,6-三甲基-1-环己烯-1-基)-,(Z,E)- (2Z,4E)-3-Methyl-5-(2',6',6'-Trimethylcyclohex-1'-En-1'-yl)-2,4-Pentadienoic Acid 14398-44-8
9-顺式-维甲酸甲基酯 [7T,9C,11T,13T]Retinoic Acid Methyl Ester 58526-50-4
9-Cis-β-Jonyliden-Essigsaeuremethylester 20110-08-1
Methyl (2E,4Z,6E)-5-Methyl-7-(2,6,6-Trimethylcyclohexen-1-yl)Hepta-2,4,6-Trienoate 14398-59-5
9-顺式视黄醇 9-Cis-Retinol 22737-97-9
9-Cis,13-Cis-Retinal 23790-80-9
维生素a Retinol 68-26-8

合成工艺路线路线简述

    9-顺式视黄醇置于manganese(Iv) Oxide,Sodium Hydroxide,Silver(L) Oxide体系中,用 甲醇 作为反应溶剂,化学反应 2.0H,以72%的收率获得产物9-顺式维甲酸
    参考文献:周环级联的9-顺式维甲酸立体控制合成
    标题:周环级联的9-顺式维甲酸立体控制合成
    摘要:据认为,本质上是环周的多米诺反应是在用芳基亚磺酰氯处理链烯醇10时引发的.该过程包括一个σ序的重排的有序序列:可逆的[2,3]-烯丙基亚磺酸盐向烯丙基亚砜的转变,然后是[2,3]-炔丙基亚磺酸盐向烯丙基亚砜的重排,最后是立体分化[1,5].-σ氢迁移导致多烯13.标记实验已证明c7至c11氢迁移的发生.据认为,[1,5]-σ氢位移的双非对映选择性是最终多烯13的单一异构体,这是由于亚砜在一个末端的电子效应和庞大的空间效应共同产生的在另一个末端有三甲基环己烯基取代基.因此,整个过程构成了由烯醛醇,特别是在共轭多烯侧链上具有7E,9Z,11Z,13E构型的类维生素a的e,Z,Z-三烯片段的立体选择性合成.这种方法在类维生素a(包括标记类似物)的合成中的应用很简单.
    DOI:10.1021/jo991757F

    海关参考信息

    专利信息


    专利号:WO-9532946-A1
    优先权日:1994-05-27
    标题 :Methods for the synthesis of 9-cis retinoids and their novel intermediates
    发明人:BENNANI YOUSSEF L
    权利人:LIGAND PHARM INC
    摘要:Methods for the synthesis of 9-cis retinoids, novel intermediates and methods for the synthesis of cyclohexadienyne nitriles and 9-cis alkyl cisoid nitriles, as well as 9-cis retinoids made using such methods are provided.

    专利号:US-2012177593-A1
    优先权日:2009-07-20
    标 题 :Synthesis of dendrimer conjugates
    发明人:BAKER JR JAMES R; ZHANG YUEHUA; THOMAS THOMMEY P; DESAI ANKUR MAHESH
    权利人:BAKER JR JAMES R; ZHANG YUEHUA; THOMAS THOMMEY P; DESAI ANKUR MAHESH; UNIV MICHIGAN
    摘要:The present invention relates to novel methods of synthesis of therapeutic and diagnostic dendrimers. In particular, the present invention is directed to novel dendrimer conjugates, novel methods of synthesizing the same, compositions comprising the conjugates, as well as systems and methods utilizing the conjugates (e.g., in diagnostic and/or therapeutic settings (e.g., for the delivery of therapeutics, imaging, and/or targeting agents (e.g., in disease (e.g., cancer, inflammatory disease) diagnosis and/or therapy, pain therapy, etc.)). Accordingly, dendrimer conjugates of the present invention may further comprise at least two different components for targeting, imaging, sensing, and/or providing a therapeutic or diagnostic material and/or monitoring response to therapy. Furthermore, the novel synthesis methods of certain embodiments of the present invention provide significant advantages with regard to total reaction time and simplicity.

    专利号:US-12391691-B2
    优先权日:2018-11-16
    标题:Synthesis of key intermediate of KRAS G12C inhibitor compound
    发明人:PARSONS ANDREW THOMAS; COCHRAN BRIAN MCNEIL; POWAZINIK IV WILLIAM; CAPORINI MARC ANTHONY
    权利人:AMGEN INC
    摘要:The present invention relates to an improved, efficient, scalable process to prepare intermediate compounds, such as compound 5M, having the structure n nuseful for the synthesis of compounds that target KRAS G12C mutations, such as

    专利号:US-2025206736-A1
    优先权日:2019-11-14
    标题 :Synthesis of kras g12c inhibitor compound
    发明人:CORBETT MICHAEL THOMAS; CAILLE SEBASTIEN
    权利人:AMGEN INC
    摘要:The present disclosure relates to an improved, efficient, scalable process to prepare intermediate compounds, such as 2-isopropyl-4-methylpyridin-3-amine, useful for the synthesis of compounds, such as Compound 9, for the treatment of KRAS G12C mutated cancers.

    专利号:US-5817845-A
    优先权日:1993-04-21
    标题:Methods for stereospecific synthesis of 11,13-cis polyene esters
    发明人:WHITE STEVEN K; HWANG CHAN KOU; WINN DAVID T
    权利人:LIGAND PHARM INC
    摘要:Methods for stereospecific synthesis of 9-cis olefins and retinoids. In one particular aspect, a cis olefin is generated via a lactol ring opening with complete retention of double bond configuration.

    专利号:US-6287818-B1
    优先权日:2000-04-25
    标 题 :Method for synthesis of N-homocysteine thiolactonyl retinamido cobalamin and uses thereof
    发明人:KAZIMIR MICHAL; WILSON II F RAY
    权利人:UNIV BAYLOR
    摘要:The present invention describes methods for the synthesis of N-homocysteine thiolactonyl retinamido cobalamin (thioretinaco), a compound that has potential anticancer, antineoplastic, antiviral, and antiatherogenic properties.
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    主要参考文献


    1: Cheer SM, Foster RH. Alitretinoin. Am J Clin Dermatol. 2000 Sep- Oct;1(5):307-14; discussion 315-6. doi: 10.2165/00128071-200001050-00005. 23(2):159-167. doi: 10.1080/14656566.2021.1998457. Epub 2021 Nov 18. 76(13):1271-1279. doi: 10.1007/s40265-016-0621-0. 5(4):373-88. doi: 10.1586/ecp.12.26. 17(3):437-43. doi: 10.1517/13543784.17.3.437. 46(2):362-363. doi: 10.1111/ced.14385. Epub 2020 Oct 10. 69(12):1625-34. doi: 10.2165/11202200-000000000-00000. 14 Suppl
    1:39-46. doi: 10.3310/hta14Suppl1/06. 28(5):351-62. doi: 10.2165/11532160-000000000-00000. 137 Suppl
    3:S111-23. French. doi: 10.1016/S0151-9638(10)70038-7. 32(1):140-142. English. doi: 10.1684/ejd.2022.4237. 23(4):1-4. 32(2):e12794. doi: 10.1111/dth.12794. Epub 2018 Dec 26. 64(10):748-51. German. doi: 10.1007/s00105-013-2593-2. 10(20):7071-7078. doi: 10.1002/cam4.4237. Epub 2021 Aug 25.

    合成参考文献


    参考文献:10.1007/s00105-011-2207-9
    摘要:Barnstedt SE. [Successful treatment of Darier disease with oral alitretinoin]. Hautarzt. 2012 Feb;63(2):139–41. doi: 10.1007/s00105-011-2207-9.
    参考文献:10.1016/j.jaad.2011.02.023
    摘要:Brehmer F, Haenssle HA, Schön MP, Emmert S. Response of recalcitrant lichen planus to alitretinoin in 3 patients. Journal of the American Academy of Dermatology. 2011 Aug;65(2):e58–60. doi: 10.1016/j.jaad.2011.02.023.
    参考文献:10.1152/ajpendo.00160.2011
    摘要:Asrih M, Pellieux C, Papageorgiou I, Lerch R, Montessuit C. Role of ERK1/2 activation in microtubule stabilization and glucose transport in cardiomyocytes. American Journal of Physiology-Endocrinology and Metabolism. 2011 Nov;301(5):E836–43. doi: 10.1152/ajpendo.00160.2011.
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