9-溴椭圆玫瑰树碱 | 18073-34-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 9-溴椭圆玫瑰树碱
• 英文名称: 9-bromo-5,11-dimethyl-6H-pyrido[4,3-b]carbazole
• 英文别名: 9-bromoellipticine；9-bromoelliptcine；9-bromo-5,11-dimethyl-6H-pyrido[4,3-b]carbazole；9-Brom-5,11-dimethyl-6H-pyrido<4.3-b>carbazol
• CAS: 18073-34-2
• 化学式: C₁₇H₁₃BrN₂
• 分子量: 325.208
• InChiKey: OSDDZVXUCKZOQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  9-溴椭圆玫瑰树碱 在 ammonium hydroxide 、 铜 、 copper(l) chloride 作用下， 反应 36.0h， 以50%的产率得到9-氨基椭圆玫瑰树碱
  参考文献：
  名称：

  Lefrancois; Lescot; Psaume, Il Farmaco, 1992, vol. 47, # 9, p. 1197 - 1206

  摘要：

  DOI：
• 作为产物：
  描述：

  椭圆玫瑰树碱 在 pyridinium hydrobromide perbromide 、 溶剂黄146 作用下， 反应 12.0h， 以60%的产率得到9-溴椭圆玫瑰树碱
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Ellipticine−Estradiol Conjugates

  摘要：

  Three ellipticine-estradiol conjugates were synthesized in an effort to target the cytotoxicity of ellipticine to estrogen-receptor positive cells. The three conjugates were prepared with linker chains extending from the 17 alpha position of the estradiol to N-2 (compound 3), N-6 (compound 4), and C-9 (compound 5) positions of ellipticine. The ellipticine-estradiol conjugates were evaluated for their abilities to bind to estrogen receptors, to inhibit topoisomerase II, and for their cytotoxicities in human cancer cell lines. Conjugates 3 and 5 displayed weak binding affinities of 0.132 and 0.303 for the estrogen receptor (relative to estradiol = 100), while conjugate 4 did not show any detectable binding to the estrogen receptor. Compound 3 was a moderate inhibitor of topoisomerase II (IC50 24.1 mu M), while 4 and 5 were inactive. Conjugate 3 was consistently more cytotoxic (GI(50) values 1-10 mu M) than compounds 4 and 5 (GI(50) values 10-100 mu M) in a variety of human cancer cell lines, None of the compounds displayed any selectivity for estrogen-receptor positive cell lines, which probably reflects their weak affinities for estrogen receptors.

  DOI：

  10.1021/jm9602930

文献信息

• Efficient microwave-assisted synthesis of ellipticine through<i>N</i>-(1,4-dimethyl-9<i>H</i>-carbazol-3-ylmethyl)-<i>N</i>- tosylaminoacetaldehyde diethyl acetal
  作者：Hsueh-Yun Lee、Grace Shiahuy Chen、Chien-Shu Chen、Ji-Wang Chern

  DOI：10.1002/jhet.319

  日期：——

  cyclization of ellipticine (1a) was dramatically improved through N‐(1,4‐dimethylcarbazol‐3‐ylmethyl)‐N‐tosylaminoacetaldehyde diethyl acetal with microwave irradiation. The overall yield of 1a starting from indole was significantly increased by 25‐fold. This new approach is superior to reported methods in yields and, reaction time, and it provides efficient access to a broad spectrum of ellipticine derivatives

  玫瑰树碱（1a）的D环环化中长期存在的问题，即低产率通过N-（1,4-二甲基咔唑-3-基甲基）N-甲苯磺酰基氨基乙醛二乙缩醛的微波辐射得到了显着改善。从吲哚开始的1a的总产量显着提高了25倍。这种新方法在收率和反应时间方面均优于已报道的方法，并且可以有效地获得广泛的玫瑰树碱衍生物。J.杂环化​​学。（2010）。
• 一种玫瑰树碱衍生物及其制备方法与应用
  申请人：中国药科大学

  公开号：CN117551095A

  公开（公告）日：2024-02-13

  本发明公开了一种结构通式为(1)椭圆玫瑰树碱衍生物，其制备方法为：以椭圆玫瑰树碱及其衍生物为原料，通过不断变换R1，A，获得一系列化合物，合成的新的化合物对结直肠肿瘤细胞具有明显的抑制作用，作用于结直肠癌细胞系HT29，其中IC50最小为1.204μM。#imgabs0#
• Ellipticines and 9-acridinylamines as inhibitors of d-alanine:d-alanine ligase
  作者：Blaž Vehar、Martina Hrast、Andreja Kovač、Janez Konc、Katherine Mariner、Ian Chopra、Alex O’Neill、Dušanka Janežič、Stanislav Gobec

  DOI：10.1016/j.bmc.2011.07.020

  日期：2011.9

  D-Alanine:D-alanine ligase (Ddl), an intracellular bacterial enzyme essential for cell wall biosynthesis, is an attractive target for development of novel antimicrobial drugs. This study focused on an extensive evaluation of two families of Ddl inhibitors encountered in our previous research. New members of both families were obtained through similarity search and synthesis. Ellipticines and 9-acridinylamines were both found to possess inhibitory activity against Ddl from Escherichia coli and antimicrobial activity against E. coli and Staphylococcus aureus. Ellipticines with a quaternary methylpyridinium moiety were the most potent among all studied compounds, with MIC values as low as 2 mg/L in strains with intact efflux mechanisms. Antimicrobial activity of the studied compounds was connected to membrane damage, making their development as antibacterial drug candidates unlikely unless analogues devoid of this nonspecific effect can be discovered. (C) 2011 Elsevier Ltd. All rights reserved.
• Antiplasmodial activity of synthetic ellipticine derivatives and an isolated analog
  作者：Andreia Montoia、Luiz F. Rocha e Silva、Zelina E. Torres、David S. Costa、Marycleuma C. Henrique、Emerson S. Lima、Marne C. Vasconcellos、Rita C.Z. Souza、Monica R.F. Costa、Andriy Grafov、Iryna Grafova、Marcos N. Eberlin、Wanderli P. Tadei、Rodrigo C.N. Amorim、Adrian M. Pohlit

  DOI：10.1016/j.bmcl.2014.04.070

  日期：2014.6

  Ellipticine has been shown previously to exhibit excellent in vitro antiplasmodial activity and in vivo antimalarial properties that are comparable to those of the control drug chloroquine in a mouse malaria model. Ellipticine derivatives and analogs exhibit antimalarial potential however only a few have been studied to date. Herein, ellipticine and a structural analog were isolated from Aspidosperma vargasii bark. A-ring brominated and nitrated ellipticine derivatives exhibit good in vitro inhibition of Plasmodium falciparum K1 and 3D7 strains. Several of the compounds were found not to be toxic to human fetal lung fibroblasts. 9-Nitroellipticine (IC50 = 0.55 mu M) exhibits greater antiplasmodial activity than ellipticine. These results are further evidence of the antimalarial potential of ellipticine derivatives. (C) 2014 Elsevier Ltd. All rights reserved.
• SAINSBURG M.; WEBB B.; SCHINAZI R., J. CHEM. SOC. PERKIN TRANS. <JCPK-BH>, 1975, PART 1, NO 3, 289-298
  作者：SAINSBURG M.、 WEBB B.、 SCHINAZI R.

  DOI：——

  日期：——