5-喹喔啉胺,2-乙基-3-甲基-(9CI) | 126527-31-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 5-喹喔啉胺,2-乙基-3-甲基-(9CI)
• 英文名称: pyridine-4-carboxaldehyde (E)-methyloxime
• 英文别名: Isonicotinaldehyde O-methyloxime；(E)-N-methoxy-1-pyridin-4-ylmethanimine
• CAS: 126527-31-9
• 化学式: C₇H₈N₂O
• 分子量: 136.153
• InChiKey: CPJAUCNNLLTZAX-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-喹喔啉胺,2-乙基-3-甲基-(9CI) 在 Ru(CO)(PPh₃)3H₂ 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 4-氰基吡啶
  参考文献：
  名称：

  钌催化的肟醚向腈的转化

  摘要：

  使用Ru（CO）（PPh 3）3 H 2和二齿配体Xantphos作为催化剂，在中性条件下实现了肟醚向腈的转化。

  DOI：

  10.1016/j.tetlet.2007.09.028
• 作为产物：
  描述：

  4-吡啶甲醛肟 、 碘甲烷 在 sodium hydroxide 、 四正辛基溴化铵 作用下， 以 水 、 苯 为溶剂， 反应 4.0h， 以39%的产率得到5-喹喔啉胺,2-乙基-3-甲基-(9CI)
  参考文献：
  名称：

  Rubina, K.; Goldberg, Yu.; Gaukhman, A., Synthetic Communications, 1989, vol. 19, # 18, p. 3129 - 3138

  摘要：

  DOI：

文献信息

• NOVEL STEREOSELECTIVE SYNTHESIS OF<i>E</i>- ARYL ALDOXIME AND KETOXIME O-ETHERS
  作者：Edgars Abele、Ramona Abele、Juris Popelis、Edmunds Lukevics

  DOI：10.1080/00304940009356280

  日期：2000.4

  systems 10% aq. NaOWC6H,/R,NX (R = n-Bu, n-Oct; X = Br, HS0,)6-9 or solid K,CO, / C,H, / 18crown-61° considerably simplifies these alkylation reactions. Recently we developed two novel FTC methods for preparation of aromatic and heteroaromatic ketoxime 0-ethers both from the ketoximes and alkyl iodides prepared in situ from alkyl chlorides'' and ketoxime 0-acetates and benzoates.'? However, the stereoselectivity

  醛肟和酮肟 0-醚，尤其是杂芳族醚，表现出广泛的生物活性。合成肟 0-醚的已知方法基于肟盐（NaH/DMF 2 或碱金属醇盐'-'）与烷基卤（主要是溴化物或碘化物）的烷基化，以及羰基化合物与 0-烷基羟胺。l" 在相转移催化 (PTC) 系统 10% aq. NaOWC6H,/R,NX (R = n-Bu, n-Oct; X = Br, HS0, )6-9 或固体 K,CO,/C,H,/18crown-61° 大大简化了这些烷基化反应。最近我们开发了两种新的 FTC 方法，用于从酮肟和烷基碘制备芳族和杂芳族酮肟 0-醚由烷基氯化物原位制备'' 和酮肟 0-乙酸酯和苯甲酸酯。'？然而，肟0-醚合成中的立体选择性通常不高。我们现在报告了一个简单的一锅 FTC 合成芳基和杂芳基醛肟和酮肟 0-醚 11-20 直接从相应的羰基化合物 1-10。该过程涉及形成相应的肟 K 盐，然后用烷基卤和炔丙基卤进行烷基化（表
• Oxime substituted imidazoquinolines
  申请人：Kshirsagar A. Tushar

  公开号：US20070066639A1

  公开（公告）日：2007-03-22

  Imidazo-containing compounds (e.g., imidazoquinolines, imidazonaphthyridines, and imidazopyridines) with an oxime substituent at the 1-position, pharmaceutical compositions containing the compounds, intermediates, and methods of use of these compounds as immunomodulators, for inducing cytokine biosynthesis in animals and in the treatment of diseases including viral and neoplastic diseases are disclosed.

  本发明涉及含咪唑基的化合物（例如咪唑喹啉，咪唑萘啶和咪唑吡啶），其在1位上具有肟基取代基，包含这些化合物的药物组合物，中间体以及这些化合物作为免疫调节剂的使用方法，用于诱导动物细胞因子生物合成和治疗包括病毒和肿瘤疾病在内的疾病。
• OXIME SUBSTITUTED IMIDAZOQUINOLINES
  申请人：Kshirsagar Tushar A.

  公开号：US20090042925A1

  公开（公告）日：2009-02-12

  Imidazo ring compounds (e.g., imidazoquinolines, 6,7,8,9-tetrahydroimidazoquinolines, imidazonaphthyridines, and imidazopyridines) with an oxime substituent at the 2-position, pharmaceutical compositions containing the compounds, intermediates, and methods of use of these compounds as immunomodulators, for inducing cytokine biosynthesis in animals and in the treatment of diseases including viral and neoplastic diseases are disclosed.

  本发明涉及带有2位置的肟取代基的咪唑环化合物（例如，咪唑喹啉，6,7,8,9-四氢咪唑喹啉，咪唑萘啉和咪唑吡啶），包含这些化合物的制药组合物，中间体以及这些化合物作为免疫调节剂的使用方法，用于诱导动物细胞因子生物合成和治疗包括病毒和肿瘤疾病在内的疾病。
• Oxime and Hydroxylamine Substituted Thiazolo [4,5-C] Ring Compounds and Methods
  申请人：Lundquist, JR. Gregory D.

  公开号：US20100240693A1

  公开（公告）日：2010-09-23

  Thiazolo[ 4,5 -c]ring compounds, (e.g. thiazolopyridine, thiazoloquinoline, 6,7,8,9 -tetrahydrothiazoloquinoline, thiazolonaphthyridine, and 6,7,8,9 -tetrahydrothiazolonaphthyridine compounds) having an oxime or hydroxylamine substituent at the 2 -position, pharmaceutical compositions containing the compounds, intermediates, and methods of making and methods of use of these compounds as immunomodulators, for modulating cytokine biosynthesis in animals and in the treatment of diseases including viral and neoplastic diseases are disclosed.

  本发明涉及一种噻唑并[4,5-c]环化合物（例如噻唑吡啶、噻唑喹啉、6,7,8,9-四氢噻唑喹啉、噻唑萘啉和6,7,8,9-四氢噻唑萘啉化合物），其在2位具有肟或羟肟取代基，以及含有该化合物的制药组合物、中间体、制备方法和用于免疫调节剂、调节动物细胞因子生物合成以及治疗包括病毒和肿瘤疾病的方法。
• Search for the Pharmacophore of Bispyridinium-Type Allosteric Modulators of Muscarinic Receptors
  作者：Mario H. Botero Cid、Ulrike Holzgrabe、Evi Kostenis、Klaus Mohr、Christian Traenkle

  DOI：10.1021/jm00036a008

  日期：1994.5

  The bis(dichlorobenzyl) ether of the bispyridinium oxime TMB 4 stabilizes antagonist binding to M(2)-cholinoceptors which is indicative of an allosteric action. More than 10 derivatives of the lead compound were synthesized to investigate structure-activity relationships. The allosteric potency of the compounds was indicated by the concentrations which retarded the rate of dissociation of [H-3]N-methylscopolamine from porcine cardiac cholinoceptors by a factor of 2 (EC(50)). Compared with TMB 4, the bis(dichlorobenzyl) derivative 4a displayed a more than 200-fold higher potency (EC(50) = 4.7 mu M). One of the dichlorobenzyl groups could be replaced by a methyl group without loss of activity (EC(50) = 4.5 mu M). Further shortening of this end of the molecule was accompanied by a moderate decline in potency to a minimum of EC(50) = 26 mu M. The second quaternary nitrogen was not a prerequisite for an allosteric activity. It is concluded that one half of the lead compound is pivotal for an interaction with the allosteric site of the M(2)-cholinoceptor, whereas the opposite end of the molecule modulates the allosteric activity.