methyl 5,7-dimethoxyindole-2-carboxylate | 27508-96-9

• 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
• 英文名称: methyl 5,7-dimethoxyindole-2-carboxylate
• 英文别名: methyl 5,7-dimethoxy-1H-indole-2-carboxylate
• CAS: 27508-96-9
• 化学式: C₁₂H₁₃NO₄
• mdl: MFCD01549462
• 分子量: 235.24
• InChiKey: ZCMLDSLEILXIFF-UHFFFAOYSA-N

物化性质

• 沸点：
  410.9±40.0 °C(Predicted)
• 密度：
  1.252±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  60.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 5,7-dimethoxyindole-2-carboxylate 在 溴 、 溶剂黄146 作用下， 以100%的产率得到methyl 4-bromo-5,7-dimethoxyindole-2-carboxylate
  参考文献：
  名称：

  Regioselective reactivity of some 5,7-dimethoxyindoles

  摘要：

  The reactivity of some 5,7-dimethoxyindoles with respect to electrophiles has been investigated. The favoured sites for reaction are C3 and C4 and regioselectivity can be controlled by the judicious arrangement of electron-withdrawing substituents. Results of formylation, acylation, the Mannich reaction, bromination and nitration are described. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.03.048
• 作为产物：
  描述：

  在 tri-nitratonitrosyl ruthenium(III) 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以93%的产率得到methyl 5,7-dimethoxyindole-2-carboxylate
  参考文献：
  名称：

  一种甲氧基取代的甲基-1H-吲哚-2-羧酸酯的制备方法

  摘要：

  本发明涉及有机合成技术领域，提供了一种甲氧基取代的甲基‑1H‑吲哚‑2‑羧酸酯的制备方法，包括以下步骤：将甲氧基取代的甲基(Z)‑2‑叠氮基‑3‑丙烯酸苯酯、钌催化剂和四氢呋喃混合后进行关环反应，得到甲氧基取代的甲基‑1H‑吲哚‑2‑羧酸酯。本发明提供的制备方法采用钌催化剂进行催化，无需使用毒性高的甲苯和二甲苯作为溶剂，即可制备得到甲氧基取代的甲基‑1H‑吲哚‑2‑羧酸酯，本发明提供的制备方法毒性较低，安全系数较高；而且本发明提供的方法纯化后得到的产物收率较高，收率在93％以上。

  公开号：

  CN111138340A

文献信息

• CBI analogues of the duocarmycins and CC-1065
  申请人：Boger L. Dale

  公开号：US20050026987A1

  公开（公告）日：2005-02-03

  An extensive series of CBI analogues of the duocarmycins and CC-1065 exploring substituent effects within the first indole DNA binding subunit is detailed. In general, substitution at the indole C5 position led to cytotoxic potency enhancements that can be ≧1000-fold providing simplified analogues containing a single DNA binding subunit that are more potent (IC 50 =2-3 pM) than CBI-TMI, duocarmycin SA, or CC-1065. The increases in cytotoxicity correlate well with accompanying increases in the rate and efficiency of DNA alkylation. This effect is more pronounced with the CBI versus DSA or CPI based analogues. Moreover, this effect is largely insensitive to the electronic character of the C5 substituent but is sensitive to the size, rigid length, and shape (sp, sp 2 , sp 3 hybridization) of this substituent consistent with expectation that the impact is due simply to its presence.

  一系列广泛的CBI类似物，包括二聚卡蜜素和CC-1065的类似物，探索了第一个吲哚DNA结合亚基中取代基效应的细节。一般来说，在吲哚C5位置的取代导致细胞毒性增强，可以达到≧1000倍，提供了更强效（IC50=2-3 pM）的含有单个DNA结合亚基的简化类似物，比CBI-TMI、二聚卡蜜素SA或CC-1065更有效。细胞毒性增加与DNA烷基化速率和效率的增加密切相关。与基于DSA或CPI的类似物相比，这种效应在CBI类似物中更为显著。此外，这种效应对于C5取代基的电子性质不太敏感，但对于取代基的大小、刚性长度和形状（sp、sp2、sp3杂化）敏感，这与预期一致，即这种影响仅仅是由于其存在。
• Concise synthesis of carbazole-1,4-quinones and evaluation of their antiproliferative activity against HCT-116 and HL-60 cells
  作者：Takashi Nishiyama、Noriyuki Hatae、Teruki Yoshimura、Sawa Takaki、Takumi Abe、Minoru Ishikura、Satoshi Hibino、Tominari Choshi

  DOI：10.1016/j.ejmech.2016.05.065

  日期：2016.10

  convenient synthesis of carbazole-1,4-quinone alkaloid koeniginequinones A and B using a tandem ring-closing metathesis with the dehydrogenation reaction sequence under an O2 atmosphere as an important step. Using this method, carbazole-1,4-quinones substituted at the 5-, 6-, 7-, and/or 8-positions have been synthesized. Moreover, 24 compounds, including koeniginequinones A and B, have been evaluated for

  我们报告了在O 2气氛下使用串联脱氧反应序列的串联闭环复分解法方便地合成咔唑1,4-醌生物碱甲酮醌A和B的重要步骤。使用这种方法，已经合成了在5-，6-，7-和/或8-位取代的咔唑-1,4-醌。此外，已经评估了24种化合物（包括甲烯乙醌A和B）对HCT-116和HL-60细胞的抗增殖活性，而6-硝基类似物对两种肿瘤细胞均表现出最有效的活性。
• A new synthesis of some 2,4ʹ-biindolyls
  作者：Glenn C. Condie、Naresh Kumar、David StC. Black

  DOI：10.24820/ark.5550190.p011.321

  日期：——
• The extended Vilsmeier reaction of dimethoxy-activated indoles
  作者：Darryl B. McConnell、Glenn C. Condie、Naresh Kumar、David StC. Black

  DOI：10.24820/ark.5550190.p011.399

  日期：——
• [EN] CBI ANALOGUES OF THE DUOCARMYCINS AND CC-1065<br/>[FR] ANALOGUES CBI DES DUOCARMYCINES ET DE CC-1065
  申请人：SCRIPPS RESEARCH INST

  公开号：WO2004101767A2

  公开（公告）日：2004-11-25

  An extensive series of CBI analogues of the duocarmycins and CC-1065 exploring substituent effects within the first indole DNA binding subunit is detailed. In general, substitution at the indole C5 position led to cytotoxic potency enhancements that can be ≥ 1000-fold providing simplified analogues containing a single DNA binding subunit that are more potent (IC50 = 2-3 pM) than CBI-TMI, duocarmycin SA, or CC-1065. The increases in cytotoxicity correlate well with accompanying increases in the rate and efficiency of DNA alkylation. This effect is more pronounced with the CBI versus DSA or CPI based analogues. Moreover, this effect is largely insensitive to the electronic character of the C5 substituent but is sensitive to the size, rigid length, and shape (sp, sp2, sp3 hybridization) of this substituent consistent with expectation that the impact is due simply to its presence.