3-hydrazino-5-methyl-1,2,4-triazino[5,6-b]indole | 3993-27-9

• 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: 3-hydrazino-5-methyl-1,2,4-triazino[5,6-b]indole
• 英文别名: (5-Methyl-[1,2,4]triazino[5,6-b]indol-3-yl)hydrazine
• CAS: 3993-27-9
• 化学式: C₁₀H₁₀N₆
• mdl: MFCD00448527
• 分子量: 214.23
• InChiKey: HIEGIMRDXIGOAG-UHFFFAOYSA-N

物化性质

• 熔点：
  221-223 °C
• 沸点：
  458.7±37.0 °C(Predicted)
• 密度：
  1.60±0.1 g/cm3(Predicted)
• 溶解度：
  13.9 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  81.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-hydrazino-5-methyl-1,2,4-triazino[5,6-b]indole 在 PPA 、 sodium nitrite 作用下， 反应 0.5h， 以48%的产率得到3-azido-5-methyl-5H-1,2,4-triazino[5,6-b]indole
  参考文献：
  名称：

  新型桥头杂环化合物的合成：嘧啶基[3',2':3,4]-1,2,4-三嗪基[5,6-b]吲哚

  摘要：

  一个新的桥头氮杂环即。11-carboethoxy-9-oxo-pyrimido[3'2':3,4]-1,2,4-triazino[5,6-b]indole 3 由 3-azido-5H-1,2 合成， 4-三嗪基[5,6-b]吲哚 2 与富马酸二乙酯反应。中间体2是通过在多磷酸存在下用NaNO2处理3-肼基-5H-1,2,4-三嗪基[5,6-b]吲哚而获得的。已经制定和讨论了形成 3 的合理机制。© 2006 Wiley Periodicals, Inc. 杂原子化学 17:272–276, 2006; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20199

  DOI：

  10.1002/hc.20199
• 作为产物：
  描述：

  1-甲基靛红 在 potassium carbonate 、 一水合肼 作用下， 以 水 为溶剂， 反应 13.0h， 生成 3-hydrazino-5-methyl-1,2,4-triazino[5,6-b]indole
  参考文献：
  名称：

  Joshi; Dandia; Baweja, Journal of the Indian Chemical Society, 1989, vol. 66, # 8-10, p. 690 - 693

  摘要：

  DOI：

文献信息

• Synthesis,¹³C-NMR characterization and antimicrobial properties of a novel series of 3-(<i>N</i>-Substituted thiocarbamoyl)hydrazino-1,2,4-triazino-[5,6-<i>b</i>]indole derivatives
  作者：A.-Mohsen M. E. Omar、Nabil H. Eshba、Hamida M. Aboushleib

  DOI：10.1002/jhet.5570230626

  日期：1986.11

  A series of 3-(N-substituted thiocarbamoyl)hydrazino-1,2,4-triazino[5,6-b]indole derivatives 3–22 has been synthesized and evaluated for in vitro antimicrobial activity. Although some of the products displayed significant activity against Staphylococcus aureus, Escherichia coli and Candida albicans, their bactericidal and bacterostatic potencies were lower than that of penicillin G. The structure of

  合成了一系列3-（N-取代的硫代氨基甲酰基）肼基-1,2,4-三嗪[5,6- b ]吲哚衍生物3-22，并对其体外抗菌活性进行了评估。尽管某些产品对金黄色葡萄球菌，大肠杆菌和白色念珠菌具有显着活性，但它们的杀菌和抑菌能力低于青霉素G。产品的结构是根据其红外，1 H-nmr和13 C-nmr光谱。
• [EN] TRIAZINE COMPOUNDS AND THEIR USE<br/>[FR] COMPOSES DE TRIAZINE ET LEUR UTILISATION
  申请人：NOVO PHARMACEUTICALS LTD DE

  公开号：WO2004096808A1

  公开（公告）日：2004-11-11

  A compound of formula (I) wherein R1 is hydrogen, alkyl, -alkyl-aryl, -alkyl-heterocycloalkyl or -alkyl-0-heterocycloalkyl; R2 is hydrogen, hydroxy, amino, nitro, alkoxy, alkyl, aryl or heteroaryl; R3 is hydrogen, alkyl or aryl; R4 is hydrogen, alkyl, aryl, heteroaryl, -CH(aryl)2, -alkyl-aryl or -C(0)0-alkyl; and R5 is alkyl, hydroxy or amino; or a pharmaceutically acceptable salt thereof; is new for use in therapy, e.g. in the treatment of Alzheimer's disease.

  式（I）的化合物中，其中R1是氢，烷基，-烷基-芳基，-烷基-杂环烷基或-烷基-0-杂环烷基；R2是氢，羟基，氨基，硝基，烷氧基，烷基，芳基或杂芳基；R3是氢，烷基或芳基；R4是氢，烷基，芳基，杂芳基，-CH（芳基）2，-烷基-芳基或-C（0）0-烷基；R5是烷基，羟基或氨基；或其药用可接受盐；用于治疗，例如用于治疗阿尔茨海默病。
• [EN] 1,2,4-TRIAZIN-3-YL-HYDRAZINE OR 5H-1,2,4-TRIAZINO'5,6-B!INDOL-3-YL-HYDRAZINE COMPOUNDS AS INHIBITORS OF BACE USEFUL IN THE TREATMENT OF ALZHEIMER<br/>[FR] COMPOSES 1,2,4-TRIAZIN-3-YL-HYDRAZINE OU 5H-1,2,4-TRIAZINO[5,6-B]INDOL-3-YL-HYDRAZINE UTILISES COMME INHIBITEURS DE BACE UTILES DANS LE TRAITEMENT DE LA MALADIE D'ALZHEIMER
  申请人：NOVO PHARMACEUTICALS LTD DE

  公开号：WO2004063196A1

  公开（公告）日：2004-07-29

  A compound of formula (I) wherein R1 is aryl and R2 is hydrogen; or R1 and R2 taken together form a group of formula (i) wherein R6 is alkyl or -alkyl-aryl; and R7 is hydrogen, halogen, alkyl, alkoxy or aryl; R3 is aryl, heteroaryl or -aryl-aryl; R4 is hydrogen, hydroxy or alkyl; and R5 is hydrogen or alkyl; or a pharmaceutically acceptable salt thereof, is new, for use in therapy, e.g. of Alzheimer's disease.

  公式（I）的化合物，其中R1为芳基，R2为氢；或者R1和R2结合形成公式（i）中的一个基团，其中R6为烷基或-烷基-芳基；而R7为氢、卤素、烷基、烷氧基或芳基；R3为芳基、杂环芳基或-芳基-芳基；R4为氢、羟基或烷基；而R5为氢或烷基；或其药用可接受盐，用于治疗，例如阿尔茨海默病。
• Sterically controlled regiospecific heterocyclization of 3-hydrazino-5-methyl-1,2,4-triazino[5,6-b]indole to 10-methyl-1,2,4-triazolo[4′,3′:2,3]1,2,4-triazino[5,6-b]indoles
  作者：M.A.E Shaban、A.Z Nasr、A.E.A Morgaan

  DOI：10.1016/s0014-827x(99)00107-x

  日期：1999.11

  3-Hydrazino-5-methyl-1,2,4-triazino[5,6-b]indole underwent sterically controlled regiospecific heterocyclizations with a variety of one-carbon cyclizing agents to give the sterically more favored linearly annulated 10-methyl-1,2,4-triazolo[4',3':2,3[1,2,4-triazino[5,6-b]indoles rather than the sterically less favored angularly annulated 10-methyl-1,2,4-triazolo[3',4':3,4]1,2,4-triazino[5,6-b]indoles. The assigned structures

  3-Hydrazino-5-methyl-1,2,4-triazino [5,6-b]吲哚与多种单碳环化剂进行空间控制的区域特异性杂环化反应，得到空间上更有利的线性环化的10-甲基-1 ，2,4-三唑并[4'，3'：2,3 [1,2,4-三嗪并[5,6-b]吲哚，而不是在空间上较不受欢迎的角环化的10-甲基-1,2,4- triazolo [3'，4'：3,4] 1,2,4-triazino [5,6-b]吲哚。通过与明确合成的真实数据，化学和光谱数据进行比较，确定了指定的结构。研究了一些制备的化合物的抗菌活性。
• Acyclo<i>C</i>-Nucleoside Analogs. Regioselective Annellation of a Triazole Ring to 5-Methyl-1,2,4-Triazino[5,6-<i>b</i>]Indole and Formation of Certain 3-Poly Hydroxyalkyl Derivatives
  作者：Nagwa Rashed、Hamida Abdel Hamid、El Sayed Ramadan、El Sayed H. El Ashry

  DOI：10.1080/07328319808003476

  日期：1998.8

  Cyclodehydrogenation of the ethylidene derivative of (5-methyl-1,2,4-triazino[5,6-b]indol-3-yl)hydrazine (1) gave the angular isomer, 1,10-dimethyl-1,2,4-triazolo[3',4':3,4][1,2,4]triazino[5,6-b] (4) The linear isomer, 3,10-dimethyl- 1,2,4-triazolo[4',3':2,3][1,2,4]triazino[5,6-b ](7) could be prepared regioselectively by the cyclodehydration of the acetyl derivative of 1. The cyclodehydrogenation was extended to the monosaccharide derivatives of 1. The role of the N-methyl group on the site of annellation has been discussed.