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MJ238 | 220627-87-2

中文名称
——
中文别名
——
英文名称
MJ238
英文别名
6-(3-carboxy-1-propyl)-5,6-dihydro-5,11-diketo-11H-indeno[1,2-c]isoquinoline;6-(3-carboxy-1-propyl)-5,6-dihydro-5,11-dioxo-11H-indeno[1,2-c]isoquinoline;4-(5,11-Dioxo-5H-indeno[1,2-C]isoquinolin-6(11H)-YL)butanoate;4-(5,11-dioxoindeno[1,2-c]isoquinolin-6-yl)butanoic acid
MJ238化学式
CAS
220627-87-2
化学式
C20H15NO4
mdl
——
分子量
333.343
InChiKey
AHIJTWCJGCWHMT-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 熔点:
    204-206 °C
  • 沸点:
    631.7±55.0 °C(Predicted)
  • 密度:
    1.44±0.1 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    2.2
  • 重原子数:
    25
  • 可旋转键数:
    4
  • 环数:
    4.0
  • sp3杂化的碳原子比例:
    0.15
  • 拓扑面积:
    74.7
  • 氢给体数:
    1
  • 氢受体数:
    4

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为产物:
    描述:
    2-(2-Carboxyphenyl)-1,3-indandion对甲苯磺酸 作用下, 以 二氯甲烷甲苯 为溶剂, 反应 30.0h, 生成 MJ238
    参考文献:
    名称:
    Synthesis and cytotoxic evaluation of novel indenoisoquinoline-propan-2-ol hybrids
    摘要:
    The synthesis of N-substituted indenoisoquinolines was performed by applying a two-step condensation between 2-carboxybenzaldehyde and phthalide, followed by treatment with various primary amines. N-allylindenoisoquinoline was subsequently selected as a substrate for hydroxybromination, providing 6-(3-bromo-2-hydroxy)indenoisoquinoline as a key intermediate for derivatization in the lactam side chain. In this way, a series of 6-(2-hydroxypropyl)indenoisoquinolines bearing various functional groups at the 3'-position were prepared, which can be considered as novel indenoisoquinoline-propan-2-ol hybrid molecules. Subsequent cytotoxic evaluation of 28 indenoisoquinolines against two human cancer cell lines (Hep-G2 and KB) demonstrated a moderate to high antiproliferative activity displayed by 11 indenoisoquinolines thus synthesized. In particular, the introduction of the 2-hydroxypropyl side chain was shown to be beneficial for the overall cytotoxic activity, pointing to the potential relevance of these novel indenoisoquinoline-propan-2-ol hybrids. (C) 2015 Elsevier Ltd. All rights reserved.
    DOI:
    10.1016/j.tetlet.2015.12.045
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文献信息

  • Combination of a Cox-2 inhibitor and a DNA topoisomerase I inhibitor for treatment of neoplasia
    申请人:Masferrer L. Jaime
    公开号:US20050187172A1
    公开(公告)日:2005-08-25
    The present invention provides combinations of a Cox-2 inhibitor and a DNA topoisomerase inhibitor and methods of use thereof for preventing and/or treating neoplasia or or a neoplasia-related disorder in a subject.
    本发明提供了一种COX-2抑制剂和DNA拓扑异构酶抑制剂的组合物,以及它们的使用方法,用于预防和/或治疗受试者中的肿瘤或与肿瘤相关的疾病。
  • indenoisoquinolines as topoisomerase inhibitors I useful as antineoplastic agents
    申请人:Purdue Research Foundation
    公开号:EP2050452A1
    公开(公告)日:2009-04-22
    A number of indenoisoquinolines were prepared and evaluated for cytotoxicity in human cancer cell cultures and for activity vs. topoisomerase I. The two most cytotoxic indenoisoquinolines proved to be cis-6-ethyl-5,6,12,13-tetrahydro-2,3-dimethoxy-8,9-(methylenedioxy)-5,11-dioxo-11H-indeno[1,2-c]isoquinoline and cis-6-allyl-5,6,12,13-tetrahydro-2,3-dimethoxy-8,9-(methylenedioxy)-5,11-dioxo-(11H)indeno[1,2-c]isoquinoline. Two of the most potent topoisomerase I inhibitors were 6-(3-carboxy-1-propyl)-5,6-dihydro-5,11-dioxo-11H-indeno[1,2-c]isoquinoline (26) and 6-ethyl-2,3-dimethoxy-8,9-(methylenedioxy)11H-indeno[1,2-c]isoquinolinium chloride (27). Two additional potent topoisomerase I inhibitors, 6-allyl-5,6-dihydro-2,3-dimethoxy-8,9-(methylenedioxy)-5,11-dioxo-11H-indeno[1,2-c]isoquinoline (13c) and 5,6-dihydro-6-(4-hydroxybut-1-yl)-2,3-dimethoxy-8,9-methylenedioxy-5,11-dioxo-(11H)indeno[1,2-c]isoquinoline (19a), did not unwind DNA and did not affect topoisomerase II.
    研究人员制备了多种茚并异喹啉,并对其在人类癌细胞培养物中的细胞毒性以及对拓扑异构酶 I 的活性进行了评估。结果表明,两种细胞毒性最强的茚异喹啉分别是顺式-6-乙基-5,6,12,13-四氢-2,3-二甲氧基-8,9-(亚甲基二氧基)-5,11-二氧代-11H-茚并[1、2-c]异喹啉和顺式-6-烯丙基-5,6,12,13-四氢-2,3-二甲氧基-8,9-(亚甲基二氧基)-5,11-二氧代-11H-茚并[1,2-c]异喹啉。两种最有效的拓扑异构酶 I 抑制剂是 6-(3-羧基-1-丙基)-5,6-二氢-5,11-二氧代-11H-茚并[1,2-c]异喹啉(26)和 6-乙基-2,3-二甲氧基-8,9-(亚甲二氧基)11H-茚并[1,2-c]异喹啉氯化铵(27)。另外两种强效拓扑异构酶 I 抑制剂是 6-烯丙基-5,6-二氢-2,3-二甲氧基-8,9-(亚甲基二氧基)-5,11-二氧代-11H-茚并[1,2-c]异喹啉(13c)和 5、6-(4-羟基丁-1-基)-2,3-二甲氧基-8,9-亚甲基二氧基-5,11-二氧代-11H-茚并[1,2-c]异喹啉(19a)不会解开 DNA,也不会影响拓扑异构酶 II。
  • Methods for reactivating genes on the inactive X chromosome
    申请人:The General Hospital Corporation
    公开号:US10961532B2
    公开(公告)日:2021-03-30
    Methods for reactivating genes on the inactive X chromosome that include administering one or both of a DNA methyltransferase (DNMT) Inhibitor and/or a topoisomerase inhibitor, e.g., etoposide and/or 5-azacytidine (aza), optionally in combination with an inhibitor of XIST RNA and/or an Xist-interacting protein, e.g., a chromatin-modifying protein, e.g., a small molecule or an inhibitory nucleic acid (such as a small inhibitory RNA (siRNAs) or antisense oligonucleotide (ASO)) that targets XIST RNA and/or a gene encoding an Xist-interacting protein, e.g., a chromatin-modifying protein.
    重新激活无活性 X 染色体上基因的方法,包括施用 DNA 甲基转移酶(DNMT)抑制剂和/或拓扑异构酶抑制剂(如依托泊苷和/或 5-氮杂胞苷(azacytidine,aza))中的一种或两种,可选择与 XIST RNA 抑制剂和/或 Xist 交互蛋白(如染色质修饰蛋白)结合使用、染色质修饰蛋白,如靶向 XIST RNA 和/或 Xist 交互作用蛋白(如染色质修饰蛋白)编码基因的小分子或抑制性核酸(如小抑制性 RNA (siRNAs) 或反义寡核苷酸 (ASO))。
  • Anticancer drug conjugates
    申请人:Ariel Scientific Innovations Ltd.
    公开号:US11007271B2
    公开(公告)日:2021-05-18
    Provided herein is a conjugate comprising two residues of structurally and/or mechanistically different anticancer bioactive agents, coupled to one another by a biocleavable linking moiety, as well as methods of treating cancer using the same and pharmaceutical compositions comprising the same.
    本文提供了一种共轭物,该共轭物由结构和/或机理上不同的抗癌生物活性剂的两个残基组成,通过可生物裂解的连接分子彼此偶联,还提供了使用该共轭物治疗癌症的方法以及包含该共轭物的药物组合物。
  • Synthesis of Cytotoxic Indenoisoquinoline Topoisomerase I Poisons
    作者:Dirk Strumberg、Yves Pommier、Kenneth Paull、Muthusamy Jayaraman、Pamela Nagafuji、Mark Cushman
    DOI:10.1021/jm9803323
    日期:1999.2.1
    A number of indenoisoquinolines were prepared and evaluated for cytotoxicity in human cancer cell cultures and for activity vs topoisomerase 1 (top1). The two most cytotoxic indenoisoquinolines proved to be cis-6-ethyl-5,6,12,13-tetrahydro-2,3-dimethoxy-8,9-(methylenedioxy)-5,11-dioxo-11H-indeno[1,2-c]isoquinoline (21) and cis-6-allyl-5,6,12,13-tetrahydro-2,3-dimethoxy-6,9-(methylenedioxy)-5,11-dioxo-11H-indeno[1,2-c]isoquinoline (22), both of which displayed submicromolar mean graph midpoints when tested in 55 human cancer cell cultures. Two of the most potent top1 inhibitors were 6-(3-carboxy-1-propyl)-5,6-dihydro-5,11-dioxo-11H-indeno[1,2-c]isoquinoline (26) and 6-ethyl-2,3-dimethoxy-8,9-(methylenedioxy)-11H-indeno[1,2-c]isoquinolinium chloride (27), both of which also inhibited top2, unwound DNA, and are assumed to be DNA intercalators. However, two additional potent top1 inhibitors, 6-allyl-5,6-dihydro-2,3-dimethoxy-8,9-(methylenedioxy)-5,11-dioxo-11H-indeno[1,2-c]isoquinoline (13c) and 5,6-dihydro-6-(4-hydroxybut-1-yl)-2,3-dimethoxy-8,9-methylenedioxy-5,11-dioxo-11H-indeno[1,2-c]isoquinoline (19a), did not unwind DNA and did not affect top2, Some of the DNA cleavage sites detected in the presence of the indenoisoquinolines were different from those seen with the camptothecins. The cleavage sites induced by the indenoisoquinolines were reversed by salt treatment, which is consistent with the reversible trapping of top1 cleavable complexes by the indenoisoquinolines. In general, the potencies of the indenoisoquinolines as top1 inhibitors did not correlate with their potencies as cytotoxic agents, as some of the most cytotoxic agents had little if any effect on top1. On the other hand, the most potent of the indenoisoquinolines vs top1 were not the most-cytotoxic. In several cases, moderate activity was observed for both cytotoxicity and activity vs top1.
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