2-oxo-1,2-dihydro-1,8-naphthyridine-3-carbonitrile | 60467-72-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-oxo-1,2-dihydro-1,8-naphthyridine-3-carbonitrile
• 英文别名: 2-oxo-1H-1,8-naphthyridine-3-carbonitrile
• CAS: 60467-72-3
• 化学式: C₉H₅N₃O
• mdl: MFCD18803535
• 分子量: 171.158
• InChiKey: HUWKQMRNPHUGMK-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C(Solv: N,N-dimethylformamide (68-12-2); water (7732-18-5))
• 沸点：
  373.1±45.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  65.8
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-oxo-1,2-dihydro-1,8-naphthyridine-3-carbonitrile 在 sodium carbonate 、 potassium carbonate 、 potassium iodide 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 2-{4-[4-(2-methylthiazol-4-yl)phenethyl]piperazin-1-yl}-1,8-naphthyridine-3-carbonitrile
  参考文献：
  名称：

  Design, synthesis, and preliminary in vitro and in vivo pharmacological evaluation of 2-{4-[4-(2,5-disubstituted thiazol-4-yl)phenylethyl]piperazin-1-yl}-1,8-naphthyridine-3-carbonitriles as atypical antipsychotic agents

  摘要：

  A series of 2-{4-[4-(2,5-disubstituted thiazolyl) phenylethyl] piperazin-1-yl}-1,8-naphthyridine-3-carbonitriles were synthesized in an effort to prepare novel atypical antipsychotic agents. The compounds were synthesized either by microwave irradiation technique or by conventional synthesis and were characterized by spectral data (IR, H-1 NMR, and MS) and the purity was ascertained by microanalysis. The D-2 and 5-HT2A affinity of the synthesized compounds was screened in vitro by radioligand displacement assays on membrane homogenates isolated from rat striatum and rat cortex, respectively. Furthermore, all the synthesized compounds were screened for their in vivo pharmacological activity in Swiss albino mice. The D-2 antagonism studies were performed using climbing mouse assay model and 5-HT2A antagonism studies were performed using quipazine-induced head twitches in mice. It was observed that none of the new chemical entities exhibited catalepsy and 10f is the most active among the synthesized compounds with 5-HT2A/D-2 ratio of 1.1286 although the standard drug risperidone exhibited 5-HT2A/D-2 ratio of 1.0989.

  DOI：

  10.3109/14756366.2010.537658
• 作为产物：
  描述：

  2-氨基-[1,8]萘啶-3-甲腈 在 硫酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 24.0h， 以85%的产率得到2-oxo-1,2-dihydro-1,8-naphthyridine-3-carbonitrile
  参考文献：
  名称：

  Shireen Mohammed, Maher Khalid, Indian Journal of Heterocyclic Chemistry, 2019, vol. 29, # 1, p. 21 - 25

  摘要：

  DOI：

文献信息

• Microwave assisted synthesis of 2-(4-substituted piperazin-1-yl)-1,8-naphthyridine-3-carbonitrile as a new class of serotonin 5-HT3 receptor antagonists
  作者：Radhakrishnan Mahesh、Ramachandran Venkatesha Perumal、Pandi Vijaya Pandi

  DOI：10.1016/j.bmcl.2004.07.060

  日期：2004.10

  A series of novel 2-(4-substituted piperazin-1-yl)-1,8-naphthyridine-3-carbonitrile 6 were prepared by microwave irradiation and conventional heating. The intermediate, 2-oxo-1,2-dihydro-1,8-naphthyridine-3-carbonitrile 3, was prepared from 2-aminonicotinaldehyde 1 and ethyl cyanoacetate 2 in the presence of piperidine under solvent free condition. The synthesized compounds were evaluated for 5-HT3

  通过微波辐射和常规加热制备了一系列新颖的2-（4-取代的哌嗪-1-基）-1，8-萘啶-3-甲腈6。在无溶剂条件下，在哌啶存在下，由2-氨基烟碱醛1和氰基乙酸乙酯2制备中间体2-氧代-1,2-二氢-1,8-萘啶-3-甲腈3。评价了合成的化合物对豚鼠回肠纵向肌肉-肠系膜神经丛（LMMP）制剂中的5-HT3拮抗作用，以对抗5-HT3激动剂2-甲基-5-HT。在测试的化合物中，在豚鼠回肠中，2-（4-烯丙基哌嗪-1-基）-1,8-萘啶-3-甲腈6d显示出最有利的5-HT3受体拮抗作用。
• Heterocyclic analogs of the antihypertensive .beta.-adrenergic blocking agent (S)-2-[3-(tert-butylamino)-2-hydroxypropoxy]-3-cyanopyridine
  作者：John J. Baldwin、Edward L. Engelhardt、Ralph Hirschmann、Gerald S. Ponticello、Joseph G. Atkinson、Burton K. Wasson、Charles S. Sweet、Alexander Scriabine

  DOI：10.1021/jm00175a012

  日期：1980.1

  heteroatom. In addition, several related examples, having additional nuclear substituents and/or groups other than CN in the position adjacent to the aminohydroxypropoxy group, were prepared, and beta-adrenoceptor antagonist activity and vasodilating potency were determined. Three compounds, thiazole 2 and isothiazoles 3 and 27, effectively lowered mean arterial pressure in the SH rat at 5 mg/kg. Compounds

  描述了一系列（S）-2- [3-（叔丁基氨基）-2-羟基丙氧基] -3-氰基吡啶（1）的等电子类似物的合成；在该组中包括噻唑，异噻唑，噻二唑，吡嗪和与结构相关的萘啶的实例。所有化合物都与1相似，因为它们在氨基羟基丙氧基侧链的邻位和在氮杂原子的间位含有一个氰基。另外，制备了几个相关的实施例，其在与氨基羟基丙氧基相邻的位置具有另外的核取代基和/或除CN以外的基团，并且确定了β-肾上腺素受体拮抗剂活性和血管舒张能力。噻唑2和异噻唑3和27这三种化合物以5 mg / kg的剂量有效降低了SH大鼠的平均动脉压。化合物2、3，
• Copper-Catalyzed<i>N</i>- and<i>O</i>-Arylation of Amides: Alternative Approaches to 3,4-Dihydroquinolin-2-ones, Quinolin-2-ones, and 12<i>H</i>-Chromeno[2,3-<i>b</i>]quinolin-12-ones
  作者：Xinying Zhang、Xiaojie Guo、Liangliang Fang、Yunping Song、Xuesen Fan

  DOI：10.1002/ejoc.201301373

  日期：2013.12

  The efficient syntheses of 3-cyanoquinolin-2-ones, 3-(2-bromobenzyl)-3-cyano-3,4-dihydroquinolin-2-ones, 3-(2-bromobenzyl)quinolin-2-ones, and 12H-chromeno[2,3-b]quinolin-12-ones through copper-catalyzed N- and O-arylation of amides by using readily available 2-bromobenzyl bromides and cyanoacetamides as starting materials were developed.

  3-氰基喹啉-2-ones、3-(2-bromobenzyl)-3-cyano-3,4-dihydroquinolin-2-ones、3-(2-bromobenzyl)quinolin-2-ones和12H-的高效合成使用容易获得的 2-溴苄基溴和氰基乙酰胺作为起始材料，通过铜催化酰胺的 N-和 O-芳基化，开发了 chromeno[2,3-b] quinolin-12-ones。
• 2,3-substituted 1,8-naphthyridines, their preparation and their use as
  申请人：BASF Aktiengesellschaft

  公开号：US05059240A1

  公开（公告）日：1991-10-22

  2,3-substituted 1,8-naphthyridines of the general formula I ##STR1## where: R is hydrogen or C.sub.1 -C.sub.4 -alkyl (n=1 or 2) R.sup.1 is amino or substituted amino, XR.sup.5, where X is oxygen or sulfur and R.sup.5 is hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.1 -C.sub.4 -alkoxycarbonyl-((C.sub.1 -C.sub.4)-alkyl, C.sub.5 -C.sub.8 -cycloakyl, substituted or unsubstituted phenyl, substituted or unsubstituted phenyl-(C.sub.1 -C.sub.3)-alkyl, halogen, isothiorhonium halide, C.sub.1 -C.sub.12 -alkyl, C.sub.1 -C.sub.4 -alkoxycarbonyl-C.sub.1 -C.sub.4 -alkyl, substituted or unsubstituted phenyl or phenyl-(C.sub.1 -C.sub.3)-alkyl, R.sup.2 is C.sub.1 -C.sub.4 -alkyl, cyano, carboxyl or a group ##STR2## where X is oxygen or sulfur, B is C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy or alkylthio, amino, mono- or dialkylamino, where each alkyl radical is of 1 to 4 carbon atoms, morpholino, piperidyl, chlorine, bromine or substituted or unsubstituted phenyl, D is C.sub.1 -C.sub.4 alkyl or NH.sub.2 and R.sup.6 is hydrogen, C.sub.1 -C.sub.8 -alkyl or alkylcarbonyl, or R.sup.1 and R.sup.2 together are --NH--N.dbd.C(CH.sub.2)--, and their environmentally tolerated salts with the proviso that R.sup.2 is not cyano, carboxyl or a carboxamido or carboxylic ester group when R.sup.1 is methyl, hydroxyl or amino (NH.sub.2), processes for their manufacture, and herbicidal agents containing a naphthyridine I as safener and at least one herbicidal active ingredient selected from the group consisting of a) 2-(4-heteroaryloxy)- or 2-(4-aryloxy)-phenoxyacetic acid derivatives and b) cyclohexenone derivatives.

  通式I为2,3-取代的1,8-萘啶，其中：R为氢或C.sub.1-C.sub.4-烷基（n=1或2），R.sup.1为氨基或取代氨基，XR.sup.5，其中X为氧或硫，R.sup.5为氢，C.sub.1-C.sub.12-烷基，C.sub.1-C.sub.4-烷氧羰基-（C.sub.1-C.sub.4）-烷基，C.sub.5-C.sub.8-环烷基，取代或未取代的苯基，取代或未取代的苯基-（C.sub.1-C.sub.3）-烷基，卤素，异硫蒽铵盐，C.sub.1-C.sub.12-烷基，C.sub.1-C.sub.4-烷氧羰基-C.sub.1-C.sub.4-烷基，取代或未取代的苯基或苯基-（C.sub.1-C.sub.3）-烷基，R.sup.2为C.sub.1-C.sub.4-烷基，氰基，羧基或基团##STR2##其中X为氧或硫，B为C.sub.1-C.sub.6-烷基，C.sub.1-C.sub.6-烷氧基或烷硫基，氨基，单烷基或双烷基氨基，其中每个烷基基团为1至4个碳原子，吗啉基，哌啶基，氯，溴或取代或未取代的苯基，D为C.sub.1-C.sub.4烷基或NH.sub.2，R.sup.6为氢，C.sub.1-C.sub.8-烷基或烷基羰基，或者R.sup.1和R.sup.2在一起为--NH--N.dbd.C(CH.sub.2)--，其环境耐受盐，但R.sup.2不为氰基，羧基或羧酰胺或羧酸酯基团，当R.sup.1为甲基，羟基或氨基（NH.sub.2）时，制造它们的过程，以及含有萘啶I作为安全剂和至少一种除草活性成分的除草剂。所述除草活性成分选自以下组合：a）2-（4-杂环氧基）-或2-（4-芳氧基）-苯氧乙酸衍生物和b）环己酮衍生物。
• Novel naphthyridines
  申请人：Merck & Co., Inc.

  公开号：US04176183A1

  公开（公告）日：1979-11-27

  Novel naphthyridines having a 3-amino-2-OR-propoxy substituent are disclosed. The compounds have .beta.-adrenergic blocking and immediate onset antihypertensive activities.

  本发明揭示了具有3-氨基-2-OR-丙氧基取代基的新型萘啶类化合物。这些化合物具有β-肾上腺素能阻滞和立即发挥的降压活性。