9-chloro-5-methyl-5H-indolo[2,3-b]quinoline | 1150313-14-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 9-chloro-5-methyl-5H-indolo[2,3-b]quinoline
• 英文别名: 9-chloroneocryptolepine；9-Chloro-5-methylindolo[2,3-b]quinoline
• CAS: 1150313-14-6
• 化学式: C₁₆H₁₁ClN₂
• 分子量: 266.73
• InChiKey: IGLNSLTZBJZDKS-UHFFFAOYSA-N

物化性质

• 熔点：
  226.87-228.47 °C
• 沸点：
  432.3±55.0 °C(predicted)
• 密度：
  1.33±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  9-chloro-5-methyl-5H-indolo[2,3-b]quinoline 、 2-氨基-5-二乙基氨基戊烷 在 air 、 palladium diacetate 、 2-(二叔丁基膦)联苯 、 sodium t-butanolate 作用下， 以 1,4-二氧六环 为溶剂， 以28%的产率得到N1,N1-diethyl-N4-(5-methyl-5H-indolo[2,3-b]quinolin-9-yl)pentane-1,4-diamine
  参考文献：
  名称：

  Synthesis and Antiplasmodial Activity of Aminoalkylamino-Substituted Neocryptolepine Derivatives

  摘要：

  A series of chloro- and aminoalkylamino-substituted neocryptolepine (5-methyl-5H-indolo[2,3-b]quinoline) derivatives were synthesized and evaluated as antiplasmodial agents. The evaluation also included cytotoxicity (MRCS cells), inhibition of beta-hematin formation, and DNA interactions (DNA-methyl green assay). Introduction of aminoalkylamino chains increased the antiplasmodial activity of the neocryptolepine core substantially. The most efficient compounds showed antiplasmodial activities in the nanomolar range. N-1,N-1-Diethyl-N-4-(5-methyl-5H-indolo[2,3-b]quinolin-8-yl)pentane-1,4-diamine 11c showed an IC50 of 0.01 mu M and a selectivity index of 1800.

  DOI：

  10.1021/jm801490z
• 作为产物：
  描述：

  3-溴-2-氯喹啉 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium acetate 作用下， 以 四氢呋喃 、 N,N-二甲基乙酰胺 、 甲苯 为溶剂， 反应 71.5h， 生成 9-chloro-5-methyl-5H-indolo[2,3-b]quinoline
  参考文献：
  名称：

  Highly efficient one-pot synthesis of D-ring chloro-substituted neocryptolepines via a condensation—Pd-catalyzed intramolecular direct arylation strategy

  摘要：

  D-ring chloro-substituted neocryptolepines have been synthesized in excellent yield starting from 3-bromo-2-chloro-1-methylquinolinium triflate via a one-pot condensation Pd-catalyzed intramolecular direct arylation strategy involving chloroanilines. The 3-bromo-2-chloro-1-methylquinolinium triflate was obtained via methylation of commercial 3-bromo-2-chloroquinoline with methyl triflate. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.10.077

文献信息

• Design, Synthesis, and Antifungal Evaluation of Neocryptolepine Derivatives against Phytopathogenic Fungi
  作者：Jia-Kai Zhu、Jian-Mei Gao、Cheng-Jie Yang、Xiao-Fei Shang、Zhong-Min Zhao、Raymond Kobla Lawoe、Rui Zhou、Yu Sun、Xiao-Dan Yin、Ying-Qian Liu

  DOI：10.1021/acs.jafc.9b06793

  日期：2020.2.26

  isolated from traditional African herbal medicine Cryptolepis sanguinolenta, and its broad spectrum of biological activities has been illuminated in past decades. In this study, neocryptolepine and its derivatives (1-49) were designed and synthesized from economical and readily available starting materials. Their structures were confirmed by proton nuclear magnetic resonance, carbon nuclear magnetic resonance

  Neocryptolepine是一种从传统非洲草药Cryptolepis sanguinolenta中分离出来的生物碱，在过去的几十年中，其广泛的生物活性得到了阐明。在这项研究中，从经济且容易获得的原料中设计和合成了新隐油菜籽及其衍生物（1-49）。通过质子核磁共振，碳核磁共振和质谱法证实了它们的结构。筛选了合成的化合物对六种农业上重要的真菌茄根丝枯病菌，灰葡萄孢（B. cinerea），禾谷镰刀菌，冬瓜霉菌，菌核菌和稻瘟病菌的抗真菌特性。体外测定结果表明，化合物5、21、24、35、40、45，47和47对EC值低于1μg/ mL的真菌表现出显着的抗真菌活性。明显地，化合物24显示出对灰葡萄芽孢杆菌的最有效的抑制效力（EC 50 ＝0.07μg/ mL），并且来自体内实验的数据表明，化合物24表现出与阳性对照的鳞茎鳞茎相当的保护活性。初步的机理研究表明，化合物24显示出令人印象深刻的孢子
• Regiodivergent Synthesis of 11 <i>H</i> ‐Indolo[3,2‐ <i>c</i> ]quinolines and Neocryptolepine from a Common Starting Material
  作者：Katja S. Håheim、Bjarte Aarmo Lund、Magne O. Sydnes

  DOI：10.1002/ejoc.202300137

  日期：——

  A common intermediate gives easy access to both neocryptolepine and isocryptolepine analogues in up to 80 % and 95 % yield, respectively.

  一种常见的中间体可以很容易地以高达 80% 和 95% 的收率分别获得新隐藤碱和异隐藤碱类似物。
• Highly efficient one-pot synthesis of D-ring chloro-substituted neocryptolepines via a condensation—Pd-catalyzed intramolecular direct arylation strategy
  作者：Steven Hostyn、Kourosch Abbaspour Tehrani、Filip Lemière、Veerle Smout、Bert U.W. Maes

  DOI：10.1016/j.tet.2010.10.077

  日期：2011.1

  D-ring chloro-substituted neocryptolepines have been synthesized in excellent yield starting from 3-bromo-2-chloro-1-methylquinolinium triflate via a one-pot condensation Pd-catalyzed intramolecular direct arylation strategy involving chloroanilines. The 3-bromo-2-chloro-1-methylquinolinium triflate was obtained via methylation of commercial 3-bromo-2-chloroquinoline with methyl triflate. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis and Antiplasmodial Activity of Aminoalkylamino-Substituted Neocryptolepine Derivatives
  作者：Ibrahim El Sayed、Pieter Van der Veken、Koen Steert、Liene Dhooghe、Steven Hostyn、Gitte Van Baelen、Guy Lemière、Bert U. W. Maes、Paul Cos、Louis Maes、Jurgen Joossens、Achiel Haemers、Luc Pieters、Koen Augustyns

  DOI：10.1021/jm801490z

  日期：2009.5.14

  A series of chloro- and aminoalkylamino-substituted neocryptolepine (5-methyl-5H-indolo[2,3-b]quinoline) derivatives were synthesized and evaluated as antiplasmodial agents. The evaluation also included cytotoxicity (MRCS cells), inhibition of beta-hematin formation, and DNA interactions (DNA-methyl green assay). Introduction of aminoalkylamino chains increased the antiplasmodial activity of the neocryptolepine core substantially. The most efficient compounds showed antiplasmodial activities in the nanomolar range. N-1,N-1-Diethyl-N-4-(5-methyl-5H-indolo[2,3-b]quinolin-8-yl)pentane-1,4-diamine 11c showed an IC50 of 0.01 mu M and a selectivity index of 1800.