ethyl 3,5-dimethyl-1H-indole-2-carboxylate | 16423-76-0

• 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: ethyl 3,5-dimethyl-1H-indole-2-carboxylate
• 英文别名: ethyl 3,5-dimethylindole-2-carboxylate
• CAS: 16423-76-0
• 化学式: C₁₃H₁₅NO₂
• mdl: MFCD00454154
• 分子量: 217.268
• InChiKey: SOBSEOUZZDHRIZ-UHFFFAOYSA-N

物化性质

• 熔点：
  131-133 °C
• 沸点：
  357.1±37.0 °C(Predicted)
• 密度：
  1.150±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  ethyl 3,5-dimethyl-1H-indole-2-carboxylate 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 29.0h， 生成 N'-(3,5-Dimethyl-1H-indole-2-carbonyl)-hydrazinecarboxylic acid ethyl ester
  参考文献：
  名称：

  Hiremath, Shivayogi P.; Hiremath, Dakshayani M.; Purohit, Muralidhar G., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, # 6, p. 571 - 576

  摘要：

  DOI：
• 作为产物：
  描述：

  在 盐酸 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以5.74 g的产率得到ethyl 3,5-dimethyl-1H-indole-2-carboxylate
  参考文献：
  名称：

  基于叠氮基环戊[b]吲哚醌的癌症特异性抗肿瘤药的设计。

  摘要：

  描述了N-未取代的吲哚和环戊[b]吲哚作为DNA定向的还原烷基化剂的优点。这些系统代表了与N-取代的和吡咯并[1，2-a]融合的系统（如丝裂霉素和丝裂霉素）的背离。当带有带有或不带有N-乙酰基的乙酸盐离去基团时，基于环戊[b]吲哚的叠氮基醌系统具有细胞毒性，并且对同基因肿瘤植入物显示出显着的体内活性。这些类似物在激活酶DT-黄递酶的高特异性和高DNA烷基化率方面均优于其他类似物。醌甲基化物中间体以及叠氮基烷基的烷基化可导致交联。制备了最活跃的吲哚物种可能的代谢物，发现保留了细胞毒性，提示体内活性可以持续。本研究中的吲哚系统显示出对黑色素瘤的选择性，并根据存在的取代基显示出对非小细胞肺癌，结肠癌，肾癌和前列腺癌的选择性。据信观察到的癌症特异性与DT-黄递酶的不同底物特异性有关。

  DOI：

  10.1021/jm990466w

文献信息

• Cytotoxic N-unsubstituted indoles and cyclopent(b)indoles and method of making and using same
  申请人：——

  公开号：US20040006054A1

  公开（公告）日：2004-01-08

  The merits of N-unsubstituted indoles and cyclopent[b]indoles as DNA-directed reductive alkylating agents are described. These systems represent a significant departure from N-substituted and pyrrolo[1,2-a] fused systems such as the mitomycins and mitosenes. The cyclopent[b]indole—based aziridinylquinone, when bearing an acetate leaving group, was found to be cytotoxic and displayed significant in vivo activity against syngeneic tumor implants. This particular analogue was unexpectedly superior to the others studied, both in terms of high specificity for the activating enzyme DT-diaphorase and in high % DNA alkylation. Alkylation by a quinone methide intermediate as well as by the aziridinyl group were examined for crosslinking. The possible metabolites of the most active indole species were prepared and found to retain cytotoxicity, strongly suggesting that in vivo activity could also be sustained. The indole systems in the present invention display selectivity for melanoma and for non small cell lung, colon, renal, and prostate cancers when administered in an effective amount. The cancer specificity observed is believed to pertain to differential substrate specificity for DT-diaphorase.

  描述了N-未取代吲哚和环戊[b]吲哚作为DNA定向还原烷基化剂的优点。这些体系与N-取代和吡咯[1,2-a]融合体系（如丝菌素和丝菌烯）有显著不同。基于环戊[b]吲哚的氮杂环喹喙醌，当带有乙酸离去基团时，被发现具有细胞毒性，并对同基因肿瘤移植物显示出显著的体内活性。这种特定的类似物在高度特异性激活酶DT-二氧还酶和高DNA烷基化百分比方面意外地优于其他研究过的类似物。通过醌亚甲基中间体和环氧丙基基团进行了交联的烷基化研究。最活跃的吲哚物种的可能代谢产物已经制备并发现保留了细胞毒性，强烈暗示体内活性也可能持续存在。本发明中的吲哚体系在有效剂量下对黑色素瘤和非小细胞肺癌、结肠癌、肾癌和前列腺癌显示出选择性。观察到的癌症特异性被认为与DT-二氧还酶的不同底物特异性有关。
• Synthesis and Antimicrobial Activity of New Substituted 10-Methyl-1,2-dihydro-1-oxo-1,2,4-triazino(4,5-a)indoles
  作者：S.B. Rajur、A.Y. Merwade、L.D. Basanagoudar、P.V. Kulkarni

  DOI：10.1002/jps.2600780917

  日期：1989.9

  Ten new 4,8-disubstituted 10-methyl-1,2-dihydro-1-oxo-1,2,4-triazino(4,5-a)indoles (5 and 6) were prepared by refluxing various 5-substituted indole-2-carbohydrazides (4) with triethylorthoformate or triethylorthoacetate in dimethylformamide. These derivatives were evaluated for their antimicrobial activity. Some of the title compounds possess fairly potent antimicrobial activity.

  通过回流各种5-取代的吲哚制备十个新的4,8-二取代的10-甲基-1,2-二氢-1-氧代-1,2,4-三嗪基（4,5-a）吲哚（5和6）。 -2-碳酰肼（4）与原甲酸三乙酯或原乙酸三乙酯在二甲基甲酰胺中的混合物。对这些衍生物的抗微生物活性进行了评估。一些标题化合物具有相当强的抗菌活性。
• Metal and Oxidant Free Construction of Substituted‐ and/or Polycyclic Indoles: A Useful Alternative to Bischler and Related Syntheses
  作者：Giacomo Mari、Lucia De Crescentini、Gianfranco Favi、Stefania Santeusanio、Fabio Mantellini

  DOI：10.1002/ejoc.202000845

  日期：2020.9.7

  wide range of substituted indoles, including complex polycyclic‐architectures were easily assembled by means of a Amberlyst 15H catalyzed synthesis that employs 1,2‐diaza‐1,3‐dienes and anilines. The metal and oxidant free methodology proposed here is characterized by good yields, total and predictable regioselectivity, and the ability to provide electron withdrawing substituted indoles.

  通过使用1,2-二氮杂-1,3-二烯和苯胺的Amberlyst 15H催化合成，可以轻松组装各种取代的吲哚，包括复杂的多环结构。本文提出的无金属和氧化剂的方法的特点是产率高，总的和可预测的区域选择性以及提供吸电子取代的吲哚的能力。
• Carboxamidothiazole derivatives, preparation, pharmaceutical compositions containing them
  申请人：Sanofi-Synthelabo

  公开号：US06380230B1

  公开（公告）日：2002-04-30

  The present invention relates to cholecystokinin (CCK)-agonist substituted thiazoles of formula: in which R1 is a substituted phenyl group, R2 is a group chosen from CH2—R7, (CH2)2—R7, S—CH2—R7, CH2—S—R7 and (C5-C8)alkyl with R7 being a (C5-C7)cycloalkyl group, and R3 is a group with R8 being a group (CH2)nR15 or and R15 being COOH or COO(C1-C4)alkyl. The invention also relates to a process for the preparation of the pharmaceutical compositions containing them and to their uses for the preparation of medicines.

  本发明涉及一种胆囊收缩素(CCK)激动剂取代噻唑的公式：其中R1是取代苯基，R2是从CH2—R7，(CH2)2—R7，S—CH2—R7，CH2—S—R7和(C5-C8)烷基中选择的一种基团，R7是(C5-C7)环烷基，R3是一个基团，其中R8是(CH2)nR15或R15为COOH或COO(C1-C4)烷基的基团。本发明还涉及制备含有它们的药物组合物的过程，以及它们用于制备药物的用途。
• Ethyl 1-(2-cyanoethyl)-3,5-dimethyl-1<i>H</i>-indole-2-carboxylate
  作者：T. N. Chandrakantha、Puttaraja. Puttaraja、M. K. Kokila、N. C. Shivaprakash

  DOI：10.1107/s0108270199001973

  日期：1999.6.15

  The title compound, C16H18N2O2, is an important precursor in the synthesis of 1,2,3,4-tetrahydropyrazinoindoles, which show excellent antihistamine, antihypertensive and central nervous system depressant properties. The carbethoxy group attached to C2 and the planar cyanoethyl group attached to N1 make dihedral angles of 11.0(4) and 75.0(3)degrees, respectively, with the mean plane of the indole ring, The C-C=N chain is linear with a bond angle of 179.3 (4)degrees.