CAS: 86639-62-5; 9-Nitrocamptothecin

该化合物是植入植物素的合成衍生物,该化合物最初产自中国树皮Camptotheca combinata,其特征是其强大的抗沙素活动,主要在于它能够抑制对DNA复制和转录至关重要的六氯丁二烯异构体A酶I酶,其化学结构包括一个硝基子组,它位于植入细胞素核心的9位置上,这增加了其细胞毒性特性.它通常是一种黄色晶体结固体,在水中可分解,但在有机溶剂中可溶解.该化合物在癌症治疗中的潜在用途,特别是在治疗各种类型的固态肿瘤方面,已经进行了研究.然而,它的临床应用受到诸如毒性和癌症细胞抗药性发展等因素的限制.研究继续探索其衍生物和模拟物,以提高癌症治疗的功效并减少副作用.

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CAS号56008-61-8 2-氨基-5-硝基苯甲醛 | CAS号110351-94-5 (S)-4-乙基-4-羟基-7... | CAS号86639-48-7 喜树碱氮氧化物 | CAS号7689-03-4 喜树碱 | CAS号86639-72-7 (4R,5bS,11aS)-4... | CAS号19685-09-7 (S)-10-羟基喜树碱 | CAS号19685-10-0 10-甲氧基喜树碱 | CAS号86639-63-6 10-氨基喜树碱

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    专利信息


    专利号:US-5212317-A
    优先权日:1990-12-20
    标 题:Methods and intermediates for the assymmetric synthesis of camptothecin and camptothecin analogs
    发明人:COMINS DANIEL L; BAEVSKY MATTHEW F
    权利人:UNIV NORTH CAROLINA STATE
    摘要:Processes for making compounds of Formulae XIV, XV, and XVII ##STR1## wherein R 6 is lower alkyl, R 7 is lower alkyl, R is lower alkyl, Y is H, F or Cl, R 8 is a moiety of Formula XVIII ##STR2## wherein n is 1, 2, or 3, R 11 is C 1 -C 4 alkyl and R 12 is the same as R 11 , or R 11 and R 12 together form cyclopentane or cyclohexane, and R 13 is: n (a) phenyl substituted 1 to 5 times with C 3 -C 7 secondary alkyl or C 4 -C 7 tertiary alkyl, or n (b) selected from the group consisting of naphthyl, anthryl, and phenanthryl optionally substituted 1 to 5 times with C 3 -C 7 secondary alkyl or C 4 -C 7 tertiary alkyl groups, n R 10 is C 6 -C 10 alkyl, aryl or alkyl aryl, n and Y is H, F or Cl, n are disclosed. These processes can be used to make optically enhanced and optically pure forms of the compounds, which are useful in the making of camptothecin and analogs thereof.

    专利号:US-5258516-A
    优先权日:1990-12-20
    标题 :Optically pure D,E ring intermediates useful for the synthesis of camptothecin and camptothecin analogs
    发明人:COMINS DANIEL L; BAEVSKY MATTHEW F
    权利人:NC STATE UNIVERSITY
    摘要:Processes for making compounds of Formulae XIV, XV, and XVII ##STR1## wherein R 6 is lower alkyl, R 7 is lower alkyl, R is lower alkyl, Y is H, F or Cl, R 8 is a compound of Formula XVIII ##STR2## wherein n is 1, 2, or 3, R 11 is C 1 -C 4 alkyl and R 12 is the same as R 11 , or R 11 and R 12 together form cyclopentane or cyclohexane, and R 13 is: n (a) phenyl substituted 1 to 5 times with C 3 -C 7 secondary alkyl or C 4 -C 7 ; tertiary alkyl, or n (b) selected from the group consisting of naphthyl, anthryl, and phenanthryl optionally substituted 1 to 5 times with C 3 -C 7 secondary alkyl or C 4 -C 7 tertiary alkyl groups, n R 10 is C 6 -C 10 alkyl, aryl or alkyl aryl, n and Y is H, F or Cl, n are disclosed. These processes can be used to make optically enhanced and optically pure forms of the compounds, which are useful in the making of camptothecin and analogs thereof.

    专利号:US-5254690-A
    优先权日:1990-12-20
    标 题 :Alkoxymethylpyridine d-ring intermediates useful for the synthesis of camptpthecin and camptothecin analogs
    发明人:COMINS DANIEL L; BAEVSKY MATTHEW F
    权利人:UNIV NORTH CAROLINA STATE
    摘要:Compounds of Formula I ##STR1## are made in accordance with the following scheme: ##STR2## wherein R may be loweralkyl; R 1 may be H, loweralkyl, loweralkoxy, or halo; R 2 , R 3 , R 4 , and R 5 may each independently be H, amino, hydroxy, loweralkyl, loweralkoxy, loweralkylthio, di(loweralkyl)amino, cyano, methylenedioxy, formyl, nitro, halo, trifluoromethyl, aminomethyl, azido, amido, hydrazino, or any of the twenty standard amino acids bonded to the A ring via the amino-nitrogen atom; Y is H and W and X are halogen. Also disclosed are novel processes for making starting materials for the scheme given above, and novel intermediates employed in these processes.

    专利号:US-5264579-A
    优先权日:1990-12-20
    标 题 :D ring intermediates for the synthesis of camptothecin and camptothecin analogs
    发明人:COMINS DANIEL L; BAEVSKY MATTHEW F
    权利人:UNIV NORTH CAROLINA STATE
    摘要:Processes for making compounds of Formulae XIV, XV, and XVII ##STR1## wherein R 6 is lower alkyl, R 7 is lower alkyl, R is lower alkyl, Y is H, F or Cl, R 8 is a compound of Formula ##STR2## wherein n is 1, 2, or 3, R 11 is C 1 -C 4 alkyl and R 12 is the same as R 11 , or R 11 and R 12 together form cyclopentane or cyclohexane, and R 13 is: n (a) phenyl substituted 1 to 5 times with C 3 -C 7 secondary alkyl or C 4 -C 7 tertiary alkyl, or n (b) selected from the group consisting of naphthyl, anthryl, and phenanthryl optionally substituted 1 to 5 times with C 3 -C 7 secondary alkyl or C 4 -C 7 tertiary alkyl groups, n R 10 is C 6 -C 10 alkyl, aryl or alkyl aryl, and Y is H, F or Cl, are disclosed. These processes can be used to make optically enhanced and optically pure forms of the compounds, which are useful in the making of camptothecin and analogs thereof.

    专利号:US-5315007-A
    优先权日:1990-12-20
    标 题:Process for making DE ring intermediates for the synthesis of camptothecin and camptothecin analogs
    发明人:COMINS DANIEL L; BAEVSKY MATTHEW F
    权利人:UNIV NORTH CAROLINA STATE
    摘要:Processes for making compounds of Formulae XIV, XV, and XVII ##STR1## wherein R 6 is lower alkyl, R 7 is lower alkyl, R is lower alkyl, Y is H, F or Cl, R 8 is a compound of Formula XVIII ##STR2## wherein n is 1, 2, or 3, R 11 is C 1 -C 4 alkyl and R 12 is the same as R 11 , or R 11 and R 12 together form cyclopentane or cyclohexane, and R 13 is: n (a) phenyl substituted 1 to 5 times with C 3 -C 7 secondary alkyl or C 4 -C 7 tertiary alkyl, or n (b) selected from the group consisting of naphthyl, anthryl, and phenanthryl optionally substituted 1 to 5 times with C 3 -C 7 secondary alkyl or C 4 -C 7 tertiary alkyl groups, n R 10 is C 6 -C 10 alkyl, aryl or alkyl aryl, n and Y is H, F or Cl, n are disclosed. These processes can be used to make optically enhanced and optically pure forms of the compounds, which are useful in the making of camptothecin and analogs thereof.

    专利号:US-5321140-A
    优先权日:1990-12-20
    标 题 :Pyridinecarboxaldehyde D-ring intermediates useful for the synthesis of camptothecin and camptothecin analogs
    发明人:COMINS DANIEL L; BAEVSKY MATTHEW F
    权利人:UNIV NORTH CAROLINA STATE
    摘要:Compounds of Formula I ##STR1## are made in accordance with the following scheme: ##STR2## wherein R may be loweralkyl; R 1 may be H, loweralkyl, loweralkoxy, or halo; R 2 , R 3 , R 4 , and R 5 may each independently be H, amino, hydroxy, loweralkyl, loweralkoxy, loweralkylthio, di(loweralkyl)amino, cyano, methylenedioxy, formyl, nitro, halo, trifluoromethyl, aminomethyl, azido, amido, hydrazino, or any of the twenty standard amino acids bonded to the A ring via the amino-nitrogen atom; Y is H and W and X are halogen. Also disclosed are novel processes for making starting materials for the scheme given above, and novel intermediates employed in these processes.

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    合成参考文献


    参考文献:10.1016/j.ejca.2005.03.009
    摘要:Baka S, Ranson M, Lorigan P, Danson S, Linton K, Hoogendam I, Mettinger K, Thatcher N. A phase II trial with RFS2000 (rubitecan) in patients with advanced non-small cell lung cancer. Eur J Cancer. 2005 Jul;41(11):1547–50. doi: 10.1016/j.ejca.2005.03.009.
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