2-甲氧基-11H-吲哚并[3,2-C]喹啉 | 4295-45-8

• 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
• 中文名称: 2-甲氧基-11H-吲哚并[3,2-C]喹啉
• 英文名称: 2-methoxy-11H-indolo[3,2-c]quinoline
• 英文别名: 2-Methoxy-11H-benzo-γ-carbolin；2-Methoxy-11H-indolo[3,2-c]chinolin
• CAS: 4295-45-8
• 化学式: C₁₆H₁₂N₂O
• 分子量: 248.284
• InChiKey: JGIGYQXWDYYTRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  37.9
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

SDS

反应信息

• 作为反应物：
  描述：

  2-甲氧基-11H-吲哚并[3,2-C]喹啉 在 sodium hydroxide 、 苄基三乙基氯化铵 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 5.67h， 生成 N,N-diethyl-2-(2-methoxy-5-oxidoindolo[3,2-c]quinolin-5-ium-11-yl)ethanamine oxide
  参考文献：
  名称：

  Structure-activity relationships of antimalarial indolo[3,2-c]quinolines [1, 2]

  摘要：

  Structure-activity relationships have been ascertained and chemical methodology developed for a series of antimalarial 3-chloroindolo[3,2-c]quinoline-5-oxides. The basic side chain as well as the ring N-oxide are critical for antimalarial activity as is a bromine or chlorine in position 3. Substitution at positions 7, 8, 9, 10 is not essential, although the most potent analog in our studies was the 8-nitro compound 4vv.

  DOI：

  10.1016/0223-5234(93)90036-e
• 作为产物：
  描述：

  1-(2-氨基-5-甲氧基苯基)-乙酮 在 polyphosphoric acid 作用下， 以 neat (no solvent) 为溶剂， 反应 8.17h， 生成 2-甲氧基-11H-吲哚并[3,2-C]喹啉
  参考文献：
  名称：

  一种基于硝基烷烃的一锅三组分合成异隐萜及其类似物的方法，具有有效的抗癌活性†

  摘要：

  开发了二代多聚磷酸介导的一锅三组分合成吲哚喹啉支架。该工艺的改进版本涉及用于安装战略 C-C 和 C-N 键和环 C 组装的亲电活化硝基烷烃。这种修改可以消除不必要的溶剂更换操作，并且所有步骤都以真正的、不间断的一锅法进行。进一步的改进涉及原位安装邻氨基的可能性。该方法的合成应用通过简明合成异隐萜生物碱及其具有有效抗癌活性的合成类似物来展示。

  DOI：

  10.1039/c8ra08155g

文献信息

• One-Pot, Three-Component Assembly of Indoloquinolines: Total Synthesis of Isocryptolepine
  作者：Alexander V. Aksenov、Dmitrii A. Aksenov、Naila A. Orazova、Nicolai A. Aksenov、Georgii D. Griaznov、Annelise De Carvalho、Robert Kiss、Véronique Mathieu、Alexander Kornienko、Michael Rubin

  DOI：10.1021/acs.joc.6b03084

  日期：2017.3.17

  Indolo[3,2-c]quinolones have been efficiently synthesized via an acid-mediated, one-pot, three-component condensation of arylhydrazines, o-aminoacetophenones, and triazines or nitriles. The synthetic application of this method is showcased by the concise synthesis of isocryptolepine alkaloid and a series of its synthetic analogues with demonstrated cancer cell antiproliferative activities.

  吲哚并[3，2- c ]喹诺酮已通过芳基肼，邻氨基苯乙酮和三嗪或腈的酸介导的一锅三组分缩合反应得到了有效合成。该方法的合成应用通过异隐油菜碱生物碱及其一系列具有证明的癌细胞抗增殖活性的合成类似物的简明合成得以展示。
• From biomass to medicines. A simple synthesis of indolo[3,2-c]quinolines, antimalarial alkaloid isocryptolepine, and its derivatives
  作者：Maxim G. Uchuskin、Arkady S. Pilipenko、Olga V. Serdyuk、Igor V. Trushkov、Alexander V. Butin

  DOI：10.1039/c2ob25836f

  日期：——

  Indolo[3,2-c]quinolines are pharmacologically attractive class of heterocyclic compounds. The method of their synthesis, based on transformation of furfural, which is a large-scale product of treatment of biomass including agricultural and forestry wastes, has been developed. This method was utilized for the total synthesis of antimalarial alkaloid isocryptolepine and its derivatives.

  吲哚并[3，2- c ]喹啉是一类具有药理吸引力的杂环化合物。它们的合成方法，基于变换糠醛已开发出大规模处理包括农业和林业废物在内的生物质的产品。该方法用于抗疟生物碱的全合成异隐油平 及其衍生物。
• 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。
• 115. Attempts to find new antimalarials. Part XXIX. The synthesis of various derivatives of 2 : 3-benz-γ-carboline
  作者：William O. Kermack、Nora E. Storey

  DOI：10.1039/jr9500000607

  日期：——
• Design of antineoplastic agents based on the '2-phenylnaphthalene-type' structural pattern—synthesis and biological activity studies of 11H-indolo[3.2-c]quinoline derivatives
  作者：L He

  DOI：10.1016/s0223-5234(02)01420-4

  日期：2003.1

  Designed as a new group of planar molecule containing the proposed 2-phenylnaphthalene-type structure, a number of 11H-indolo[3.2-c]quinoline derivatives were synthesized and evaluated biologically. Several compounds were found to possess cytotoxic activity against the growth of human promyclocytic leukemia cells (HL-60), against the small cell lung cancer (SCLC), and showed good response in the National Cancer Institute preclinical antitumor drug discovery 60-cell line panel. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.