CAS: 146478-72-0; Fr 901464

该化合物是一种复杂的有机化合物,具有多种功能组和立体中心的特点,具有乙酰氧化合物组的特点,表明有机溶剂中具有潜在的反应性和溶解性.二氧化锡结构的存在表明一种独特的循环安排可能有助于其生物活动.该化合物还包含多个手性中心,可影响其立体化学和与生物系统的互动.该结构表明在制药或作为生物活性化合物中的潜在应用,尽管具体的生物活动需要进一步研究.碳链和功能组的复杂安排凸显了其复杂性,使其成为合成有机化学和药用化学研究的热点.

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上下游产品

Spliceostatin A 391611-36-2
(Z)-(S)-4-Hydroxy-Pent-2-Enoic Acid ((2R,3R,5S,6S)-6-{(2E,4E)-5-[(3R,4R,5R,7S)-4-(Tert-Butyl-Dimethyl-Silanyloxy)-7-Methoxy-7-Methyl-1,6-Dioxa-Spiro[2.5]Oct-5-Yl]-3-Methyl-Penta-2,4-Dienyl}-2,5-Dimethyl-Tetrahydro-Pyran-3-yl)-Amide 878673-41-7
(Z,4S)-4-[tert-Butyl(Dimethyl)Silyl]Oxy-N-[(2R,3R,5S,6S)-6-[(2E,4E)-5-[(3R,4R,5R,7S)-4-[tert-Butyl(Dimethyl)Silyl]Oxy-7-Methoxy-7-Methyl-1,6-Dioxaspiro[2.5]Octan-5-Yl]-3-Methylpenta-2,4-Dienyl]-2,5-Dimethyloxan-3-Yl]Pent-2-Enamide 878673-40-6
(3R,4R,5R,7S)-7-Methyl-5-Vinyl-1,6-Dioxa-Spiro[2.5]Octane-4,7-Diol 882028-32-2
(2Z,2'R,2''E,3'R,4S,5'S,6'S)-N-{6'-[4''-(1''',3'''-Benzothiazol-2'''-Ylsulfonyl)-3''-Methylbut-2''-En-1''-Yl]-2',5'-Dimethyltetrahydropyran-3'-Yl}-4-T-Butyldimethylsilyloxypent-2-Enamide 878673-39-3

合成工艺路线路线简述

    📜(2R,3R,5S,6S)-6-Allyl-2,5-Dimethyltetrahydro-2H-Pyran-3-Amine置于grela'S Catalyst,N,N-二异丙基乙胺,N-[(Dimethylamino)-3-Oxo-1H-1,2,3-Triazolo[4,5-B]Pyridin-1-Yl-Methylene]-N-Methylmethanaminium Hexafluorophosphate体系中,用 四氢呋喃,二氯甲烷,1,2-二氯乙烷,乙腈 用作溶剂,化学反应 31.0H,反应生成4(S)-乙酰氧基-N-[(2R,3R,5S,6S)-6-[5-[(3R,4R,5R,7S)-4,7-二羟基-7-甲基-1,6-二氧杂螺[2.5]辛烷-5-基]-3-甲基-2(E),4(E)-戊二烯基]-2,5-二甲基四氢吡喃-3-基]-2(Z)-戊烯酰胺
    参考文献:Fr901464 的全合成,一种调节癌基因和肿瘤抑制基因转录的抗肿瘤剂
    标题:Fr901464 的全合成,一种调节癌基因和肿瘤抑制基因转录的抗肿瘤剂
    摘要:Fr901464 是一种有效的抗癌剂,可调节癌基因和肿瘤抑制基因的转录.Fr901464 的收敛对映选择性合成以 13 个线性步骤完成.合成方法的核心是二烯-烯交叉烯烃复分解反应反应生成C6-C7 烯烃,不使用保护基团作为最终偶联.其他关键反应包括 Zr/ag 促进的炔化以设置 C4 立体中心,温和且化学选择性的 Red-Al 还原,立体选择性 Mislow-Evans 型 [2,3]-Sigmatropic 重排以安装 C5 立体中心,Carreira 不对称炔基化以反应生成C4' 立体中心,以及高效的闭环复分解-烯丙基氧化序列以形成不饱和内酯.
    Doi:10.1021/ja058216U

    海关参考信息

    专利信息


    专利号:US-9771377-B2
    优先权日:2012-12-21
    标 题 :Synthesis of FR901464 and analogs with antitumor activity
    发明人：KOIDE KAZUNORI; OSMAN SAMI SAIF ELDIN ALI
    权利人:UNIV OF PITTSBURGH—OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCATION
    摘要:The present invention provides novel analogs of FR901464, as well as an improved methodology for preparing FR901464 and its analogs. These compounds display an anti-cancer activity and are candidates for therapies against a number of disease states associated with dysfunctional RNA splicing.

    专利号:US-8309599-B2
    优先权日:2006-09-08
    标题 :Synthesis of FR901464 and analogs with antitumor activity
    发明人：KOIDE KAZUNORI; ALBERT BRIAN J; SIVARAMAKRISHNAN ANANTHAPADMANABHAN
    权利人:KOIDE KAZUNORI; ALBERT BRIAN J; SIVARAMAKRISHNAN ANANTHAPADMANABHAN; UNIV PITTSBURGH
    摘要:The present invention provides novel analogs of FR901464, as well as an improved methodology for preparing FR901464 and its analogs. These compounds display an anti-cancer activity and are candidates for therapies against a number of disease states associated with dysfunctional RNA splicing.

    专利号:US-11584754-B2
    优先权日:2016-06-08
    标 题 :Derivatives of thailanstatin A, methods of treatment and methods of synthesis thereof
    发明人：NICOLAOU KYRIACOS C; RHOADES DEREK; KUMAR SOUNDARAPANDIAN M; PATTANAYAK MANAS R; LAMANI MANJUNATH
    权利人:UNIV RICE WILLIAM M
    摘要:In one aspect, the present disclosure provides analogs of thailanstatin of the formula wherein the variables are as defined herein. In another aspect, the present disclosure also provides methods of preparing the compounds disclosed herein. In another aspect, the present disclosure also provides pharmaceutical compositions and methods of use of the compounds disclosed herein.

    专利号:US-2008096879-A1
    优先权日:2006-09-08
    标题:Synthesis of fr901464 and analogs with antitumor activity

    专利号:US-7825267-B2
    优先权日:2006-09-08
    标 题 :Synthesis of FR901464 and analogs with antitumor activity

    专利号:US-2015307512-A1
    优先权日:2012-12-21
    标题 :Synthesis of fr901464 and analogs with antitumor activity

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    主要参考文献


    1: Cretu C, Gee P, Liu X, Agrawal A, Nguyen TV, Ghosh AK, Cook A, Jurica M, Larsen NA, Pena V. Structural basis of intron selection by U2 snRNP in the presence of covalent inhibitors. Nat Commun. 2021 Jul 23;12(1):4491. doi: 10.1038/s41467-021-24741-1.
    2: Zhao H, Zhang B, Ma LF, Shi LM, Zhan ZJ. Cytotoxic Spliceostatin Analogs from Pseudomonas sp. Chem Biodivers. 2019 Sep;16(9):e1900266. doi: 10.1002/cbdv.201900266. Epub 2019 Aug 8. 10(3):352-367. doi: 10.18632/oncotarget.26564.
    4: Zhao Y, Zhao J, Lu C, Zhang H, Qi H, Jiang S, Guo X, Wang J, Xiang W. Two new spliceostatin analogs from the strain Pseudomonas sp. HS-NF-1408. J Antibiot (Tokyo). 2018 Jul;71(7):667-671. doi: 10.1038/s41429-018-0052-0. Epub 2018 Apr 17. 23(1):47-57. doi: 10.1261/rna.058065.116. Epub 2016 Oct 17.

    合成参考文献


    摘要:Negishi, E.; Wang, G., Science of Synthesis, (2009) 46, 275.
    参考文献:10.1021/jo500800k
    摘要:Ghosh AK, Chen ZH, Effenberger KA, Jurica MS. Enantioselective total syntheses of FR901464 and spliceostatin A and evaluation of splicing activity of key derivatives. J Org Chem. 2014 Jun 20;79(12):5697–709.
    参考文献:10.7164/antibiotics.49.1196
    摘要:Nakajima H, Sato B, Fujita T, Takase S, Terano H, Okuhara M. New antitumor substances, FR901463, FR901464 and FR901465. I. Taxonomy, fermentation, isolation, physico-chemical properties and biological activities. J Antibiot (Tokyo). 1996 Dec;49(12):1196–203. doi: 10.7164/antibiotics.49.1196.
    参考文献:10.7164/antibiotics.49.1204
    摘要:Nakajima H, Hori Y, Terano H, Okuhara M, Manda T, Matsumoto S, Shimomura K. New antitumor substances, FR901463, FR901464 and FR901465. II. Activities against experimental tumors in mice and mechanism of action. J Antibiot (Tokyo). 1996 Dec;49(12):1204–11. doi: 10.7164/antibiotics.49.1204.
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