2,3-二甲基喹啉-4,6-二胺 | 828930-83-2

• 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: 2,3-二甲基喹啉-4,6-二胺
• 英文名称: 4,6-diamino-2,3-dimethylquinoline
• 英文别名: 2,3-dimethyl-quinoline-4,6-diyldiamine；2,3-Dimethyl-chinolin-4,6-diyldiamin；2,3-Dimethylquinoline-4,6-diamine
• CAS: 828930-83-2
• 化学式: C₁₁H₁₃N₃
• 分子量: 187.244
• InChiKey: CBEVFUCYVCKYPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  64.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3-二甲基喹啉-4,6-二胺 、 2-((4-乙基苯氧基)甲基)苯甲酰氯 在 吡啶 作用下， 反应 3.0h， 以38%的产率得到N-(4-amino-2,3-dimethylquinolin-6-yl)-2-[(4-ethylphenoxy)methyl]benzamide
  参考文献：
  名称：

  A new synthetic approach of N-(4-amino-2-methylquinolin-6-yl)-2-(4-ethylphenoxymethyl)benzamide (JTC-801) and its analogues and their pharmacological evaluation as nociceptin receptor (NOP) antagonists

  摘要：

  A series of 4-amino-2-methylquinoline and 4-aminoquinazoline derivatives, including the reference NOP antagonist JTC-801, were synthesized by an alternative pathway and their in vitro pharmacological properties were investigated. 3-Substitution of the quinoline ring resulted very critical for affinity. So 3-methyl derivative 4j showed a similar potency compared with the reference 4h while bulky lipophilic or electron withdrawing groups in the same position strongly decreased affinity. Structural and conformational requirements for affinity were outlined by NOE NMR and computational methods and suggestions for a pharmacophore model design were provided. (C) 2004 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.09.009
• 作为产物：
  描述：

  2-氰基-4-硝基苯胺 在 氢氧化钾 、 aluminum nickel 、 tin(ll) chloride 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 6.0h， 生成 2,3-二甲基喹啉-4,6-二胺
  参考文献：
  名称：

  A new synthetic approach of N-(4-amino-2-methylquinolin-6-yl)-2-(4-ethylphenoxymethyl)benzamide (JTC-801) and its analogues and their pharmacological evaluation as nociceptin receptor (NOP) antagonists

  摘要：

  A series of 4-amino-2-methylquinoline and 4-aminoquinazoline derivatives, including the reference NOP antagonist JTC-801, were synthesized by an alternative pathway and their in vitro pharmacological properties were investigated. 3-Substitution of the quinoline ring resulted very critical for affinity. So 3-methyl derivative 4j showed a similar potency compared with the reference 4h while bulky lipophilic or electron withdrawing groups in the same position strongly decreased affinity. Structural and conformational requirements for affinity were outlined by NOE NMR and computational methods and suggestions for a pharmacophore model design were provided. (C) 2004 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.09.009

文献信息

• Dual molecules containing peroxy derivative, the synthesis and therapeutic applications thereof
  申请人：Cazelles Jerome

  公开号：US20070021423A1

  公开（公告）日：2007-01-25

  The invention relates to dual molecule compounds containing a peroxide derivative, to processes for the synthesis of such compounds, to pharmaceutical compositions comprising such compounds, and to methods of treatment and prevention of malaria comprising administering such compounds and such pharmaceutical compositions.

  这项发明涉及含有过氧化物衍生物的双分子化合物，涉及合成这种化合物的方法，涉及包括这种化合物的药物组合物，以及涉及通过给予这种化合物和这种药物组合物来治疗和预防疟疾的方法。
• Quaternary salts of pyrimidylaminoquinolines
  申请人：MURIEL RUTH CURD

  公开号：US02585909A1

  公开（公告）日：1952-02-19

  Mono- and di-quaternary salts of pyrimidylaminoquinolines having trypanocidal activity are made by reacting a quaternary salt of pyrimidine substituted in the 2-, 4- (or 6-) positions by amino or lower alkylamino-groups, in another of the 2-, 4- (or 6-) positions by a lower alkyl-, amino-, or lower alkylamino-group, and in one of the remaining 2-, 4- (or 6-) groups by a halogen atom or -SR group, R being hydrocarbon, with an amino-quinoline, substituted in the 4-position by amino-, or lower alkylamino, and which may be further substituted by lower alkyl groups, or with a quaternary salt thereof, in presence of an acid with or without a liquid medium. The amino-quinoline may be in the form of a salt thereof, or in the form of substances which will give rise to it under the reaction conditions. The products must contain at least an alkylamino-substituent in the pyrimidine nucleus or in 4-position of the quinoline nucleus. In examples, the quaternary salts of aminopyrimidines substituted by chlorine, bromine or iodine or thioalkyl in the 2- or 4-position, and with other groups as defined, are treated with 4- or 6-aminoquinolines having other substituents as defined above, or with their acetyl derivatives or quaternary salts, to give the mono- or di-salts of the corresponding pyrimidylaminoquinolines, in which the-NH-group is attached at the 2-, 4-, or 6-positions of the pyrimidine nucleus and the 6-positions of the quinoline nucleus, and the alkyl groups may be methyl, ethyl, isopropyl and butyl. The products include 4-alkylamino- or amino-6-(21-amino- or alkylamino-61-alkyl- or amino-pyrimidyl-41-amino)-methyl quinoline-dimethiodides, dimethochlorides, &c., and the corresponding quinolines. 4 - Alkylamino 6 - acetyl - aminoquinaldines are obtained by the action of alkylamines on the 4-chloro-compound and may be hydrolysed and quaternated; the corresponding methylaminequinoline derivative is obtained by hydrolysis of 4-hydroxy-6-acetylamino-quinoline with POCl3 to give the 2-chloro derivative, and condensation with methylamine, and may be quaternated. Specifications 658,202 and 658,204 are referred to.

  制备具有抗锥虫活性的嘧啶基氨基喹啉的单和双季铵盐，通过将2-、4-（或6-）位置取代氨基或较低烷基氨基基团的嘧啶季铵盐与2-、4-（或6-）位置中的较低烷基、氨基或较低烷基氨基基团以及剩余的2-、4-（或6-）位置中的卤素原子或-SR基（R为碳氢）取代的氨基喹啉或其季铵盐在酸性介质中或无液体介质的情况下反应制得。氨基喹啉可以是其盐的形式，或者是在反应条件下会产生其形式的物质。产品必须至少含有嘧啶核或喹啉核4-位置的烷基氨基取代基。例如，用氯、溴或碘或硫代烷基在2-或4-位置取代的氨基嘧啶季铵盐，以及具有上述其他取代基的4-或6-氨基喹啉或其乙酰衍生物或季铵盐进行反应，制备相应的嘧啶基氨基喹啉的单或双季铵盐，其中-NH基团附在嘧啶核的2-、4-或6-位置和喹啉核的6-位置，烷基可以是甲基、乙基、异丙基和丁基。产品包括4-烷基氨基或氨基-6-(2-氨基或烷基氨基-6-烷基或氨基-嘧啶基-4-氨基)-甲基喹啉二甲硫醇盐、二甲氯化物等，以及相应的喹啉。通过在4-氯化合物上作用烷基胺得到4-烷基氨基-6-乙酰氨基喹啉，可以水解和季铵化；通过将4-羟基-6-乙酰氨基喹啉与POCl3水解以得到2-氯衍生物，再与甲基胺缩合，可以得到相应的甲胺喹啉衍生物，并可以季铵化。参考规范658,202和658,204。
• QUINOLINE DERIVATIVES FOR MODULATING DNA METHYLATION
  申请人：Phiasivongsa Pasit

  公开号：US20110256092A1

  公开（公告）日：2011-10-20

  Quinoline derivatives, particularly 4-anilinoquinoline derivatives, are provided. Such quinoline derivatives can be used for modulation of DNA methylation, such as effective inhibition of methylation of cytosine at the C-5 position, for example via selective inhibition of DNA methyltransferase DNMT1. Methods for synthesizing numerous 4-anilinoquinoline derivatives and for modulating DNA methylation are provided. Also provided are methods for formulating and administering these compounds or compositions to treat conditions such as cancer and hematological disorders.

  提供了喹啉衍生物，特别是4-苯胺基喹啉衍生物。这种喹啉衍生物可以用于调节DNA甲基化，例如通过选择性抑制DNA甲基转移酶DNMT1，有效抑制C-5位置的胞嘧啶甲基化。提供了合成多种4-苯胺基喹啉衍生物和调节DNA甲基化的方法。还提供了制剂和给药这些化合物或组合物以治疗癌症和血液系统疾病的方法。
• Jensch, Justus Liebigs Annalen der Chemie, 1950, vol. 568, p. 73,79
  作者：Jensch

  DOI：——

  日期：——
• DE839641
  申请人：——

  公开号：——

  公开（公告）日：——