5,6-bis(4-methoxyphenyl)-2-chloropyrazine | 106615-33-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5,6-bis(4-methoxyphenyl)-2-chloropyrazine
• 英文别名: 2,3-bis(p-methoxyphenyl)-5-chloropyrazine；5-chloro-2,3-bis(4-methoxyphenyl)pyrazine
• CAS: 106615-33-2
• 化学式: C₁₈H₁₅ClN₂O₂
• 分子量: 326.782
• InChiKey: VISDDJPOXWTMHT-UHFFFAOYSA-N

物化性质

• 沸点：
  426.2±45.0 °C(Predicted)
• 密度：
  1.226±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  44.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,6-bis(4-methoxyphenyl)-2-chloropyrazine 、 alkaline earth salt of/the/ methylsulfuric acid 生成 2,3-Di(4-methoxyphenyl)-5-EtO-pyrazine
  参考文献：
  名称：

  Measurement and prediction of hydrophobicity parameters for highly lipophilic compounds: Application of the HPLC column-switching technique to measurement of log P of diarylpyrazines

  摘要：

  In the preparatory stage of structure-activity relationship (QSAR) studies of anti-platelet aggregant pyrazine derivatives, log P values (P: 1-octanol/water partition coefficient) of diarylpyrazines were measured by a newly developed HPLC column-switching technique. The system consists of two processes: (1) adsorption of the sample at the top end of a short precolumn, and then (2) quantifying the enriched analyte by a conventional analytical column. By using the log P values thus obtained, the correction factor for the steric hindrance caused by the vicinal diphenyl groups was estimated. The log k values (k; retention factor) were also measured with methanol-buffer (pH 7.4) eluents and related to log P. The eluent of 50% methanol content (M50) gave a good linear relationship over a wide range of log P (-0.3< log P < 5.2), indicating that log k(M50) parameter is useful for predicting the log P value.

  DOI：

  10.1021/js990112s
• 作为产物：
  描述：

  4,4'-二甲氧基苯酚酯 在 sodium hydroxide 、 三氯氧磷 作用下， 以 乙醇 、 苯 为溶剂， 生成 5,6-bis(4-methoxyphenyl)-2-chloropyrazine
  参考文献：
  名称：

  Synthesis and bioactivities of novel pyridazine derivatives: inhibitors of interleukin-1 beta (IL-1β) production

  摘要：

  New pyridazine derivatives were prepared, and their abilities to inhibit IL-1 beta production were evaluated. Some compounds showed potent inhibitory activity against IL-1 beta production in HL-60 cells stimulated with lipopolysaccharide (LPS). The synthesis and structure-activity relationships of these compounds are described. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00432-2

文献信息

• Anti-Platelet Aggregation Activity of Some Pyrazines.
  作者：Akihiro OHTA、Hiromitsu TAKAHASHI、Naoomi MIYATA、Hiroyuki HIRONO、Toyotaka NISHIO、Etsuo UCHINO、Kenji YAMADA、Yutaka AOYAGI、Yasushi SUWABE、Masayuki FUJITAKE、Takahiro SUZUKI、Kazuo OKAMOTO

  DOI：10.1248/bpb.20.1076

  日期：——

  This report describes the anti-platelet aggregation activity of 48 pyrazines. Among alkyl- and arylpyrazines tested, 2, 3-diphenylpyrazines showed the strongest anti-platelet aggregation activity. Then, various substituents were introduced into the phenyl groups, and the 2, 3-bis(p-methoxyphenyl)pyrazine derivatives were consequently found to possess considerably strong inhibitory activity.

  本报告介绍了 48 种吡嗪类化合物的抗血小板聚集活性。在测试的烷基和芳基吡嗪中，2, 3-二苯基吡嗪的抗血小板聚集活性最强。然后，在苯基上引入了各种取代基，结果发现 2，3-双（对甲氧基苯基）吡嗪衍生物具有相当强的抑制活性。
• Pyrazine derivatives useful as platelet aggregation inhibitors
  申请人：Terumo Kabushiki Kaisha

  公开号：US04788197A1

  公开（公告）日：1988-11-29

  Novel pyrazine derivatives are disclosed. The compounds possess a potent platelet aggregation-inhibiting activity and are effective for preventing diseases caused by aggregation of the platelet, for example, myocardial infarction and cerebral thromobsis. Representative examples of the pyrazine derivatives includes 2,3-bis(p-chlorophenyl)-5-methylpyrazine, 2,3-bis(p-methoxyphenyl)-5-methylpyrazine, 2,3-diphenyl-5-benzylpyrazine, 2,3-diphenyl-5-(p-methoxybenzyl)pyrazine, 2,3-bis(p-methoxyphenyl)-5-isopropylpyrazine, 2,3-bis(p-methoxyphenyl)-5-(2-thienylmethyl)pyrazine and 2,3-bis(p-methoxyphenyl)-5,6-dimethylpyrazine. The pyrazine derivatives can be generally prepared by heating a benzil derivative and a 1,2-diaminoethane derivative to produce a dihydropyrazine derivative and heating the resulting compound with sulfur at 100.degree.-180.degree. C.

  揭示了一种新型吡嗪衍生物。这些化合物具有强大的抑制血小板聚集活性，并且对预防由血小板聚集引起的疾病，例如心肌梗死和脑血栓形成，具有有效性。吡嗪衍生物的代表性例子包括2,3-双(对氯苯基)-5-甲基吡嗪，2,3-双(对甲氧基苯基)-5-甲基吡嗪，2,3-二苯基-5-苄基吡嗪，2,3-二苯基-5-(对甲氧基苄基)吡嗪，2,3-双(对甲氧基苯基)-5-异丙基吡嗪，2,3-双(对甲氧基苯基)-5-(2-噻吩甲基)吡嗪和2,3-双(对甲氧基苯基)-5,6-二甲基吡嗪。这些吡嗪衍生物通常可以通过将苯酮衍生物和1,2-二氨基乙烷衍生物加热以产生二氢吡嗪衍生物，然后将得到的化合物与硫在100度至180度C下加热制备而成。
• Heterocyclic compound derivatives and medicines
  申请人：——

  公开号：US20040102436A1

  公开（公告）日：2004-05-27

  The present invention provides a compound which is useful as a PGI 2 receptor agonist, and a pharmaceutical composition. The present invention is directed to a pharmaceutical composition comprising a compound represented by the following formula [1]: 1 (R 1 and R 2 are the same or different and each represents optionally substituted aryl, Y represents N or CH, Z represents N or CH, A represents NH, NR 5 , O, S, or ethylene, R 5 represents alkyl, D represents alkylene or alkenylene, E represents phenylene or single bond, G represents O, S, or CH 2 , R 3 and R 4 are the same or different and each represents hydrogen or alkyl, Q represents carboxy, alkoxycarbonyl, tetrazolyl, carbamoyl, or N-(alkylsulfonyl)carbamoyl), or a pharmaceutically acceptable salt thereof as an active ingredient.

  本发明提供了一种作为PGI2受体激动剂有用的化合物和制药组合物。本发明涉及一种制药组合物，其包括由以下式子[1]表示的化合物：1（其中R1和R2相同或不同，每个表示可选择取代的芳基，Y表示N或CH，Z表示N或CH，A表示NH、NR5、O、S或乙烯，R5表示烷基，D表示烷基或烯基，E表示苯基或单键，G表示O、S或CH2，R3和R4相同或不同，每个表示氢或烷基，Q表示羧基、烷氧羰基、四唑基、氨基甲酰基或N-(烷基磺酰)氨基甲酰基），或其药学上可接受的盐作为活性成分。
• Pyrazine derivatives
  申请人：TERUMO KABUSHIKI KAISHA trading as TERUMO CORPORATION

  公开号：EP0194686A1

  公开（公告）日：1986-09-17

  Novel pyrazine derivatives are disclosed. The compounds possess a potent platelet aggregation-inhibiting activity and are effective for preventing diseases caused by aggregation of the platelet, for example, myocardial infarction and cerebral thrombosis. Representative examples of the pyrazine derivatives include 2,3-bis (p-chlorophenyl)-5-methylpyrazine, 2,3-bis(p-methoxyphenyl)-5-methylpyrazine, 2,3-diphenyl-5-benzylpyrazine, 2,3-diphenyl-5-(p-methoxybenzyl) pyrazine, 2,3-bis (p-methoxyphenyl)-5-isopropylpyrazine, 2,3-bis)p-methoxyphenyl)-5-(2-thienylmethyl) pyrazine and 2,3-bis-(p-methoxyphenyl)-5,6-dimethylpyrazine. The pyrazine derivatives can be generally prepared by heating a benzil derivative and a 1, 2-diaminoethane derivative to produce a dihydropyrazine derivative and heating the resulting compound with sulfur at 100 - 180°C.

  本研究公开了新型吡嗪衍生物。这些化合物具有强效的血小板聚集抑制活性，可有效预防由血小板聚集引起的疾病，如心肌梗塞和脑血栓。吡嗪衍生物的代表性实例包括 2,3-双（对氯苯基）-5-甲基吡嗪、2,3-双（对甲氧基苯基）-5-甲基吡嗪、2,3-二苯基-5-苄基吡嗪、2、2,3-双（对甲氧基苯基）-5-异丙基吡嗪、2,3-双（对甲氧基苯基）-5-（2-噻吩基甲基）吡嗪和 2,3-双（对甲氧基苯基）-5,6-二甲基吡嗪。 吡嗪衍生物的制备方法一般是加热苯偶姻衍生物和 1，2-二氨基乙烷衍生物，生成二氢吡嗪衍生物，然后在 100-180°C 下用硫加热生成的化合物。
• PYRAZINE DERIVATIVES AND MEDICINAL PREPARATION CONTAINING SAME
  申请人：TERUMO KABUSHIKI KAISHA

  公开号：EP0397859A1

  公开（公告）日：1990-11-22

  Pyrazine derivatives represented by general formula (I), wherein X represents a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group or a cyano group, R1 represents a hydrogen atom, a lower alkyl group or a group of (a) (wherein X is as defined above), R2 represents a hydrogen atom, a halogen atom or (a) (wherein X is as defined above), R3 represents a hydrogen atom, a halogen atom, a lower alkyl group, a cyano group, a naphthylmethyl group, a benzyl group or (b) (wherein R4represents a hydrogen atom, a halogen atom or a lower alkylamino group), a carboxyl group or a lower alkoxycarbonyl group or, when taken together, R2 and R3 represent a cyclohexane ring or a benzene ring together with the carbon atoms to which they are bound, provided that the case where X represents a hydrogen atom, R, represents (a) (wherein X represents a hydrogen atom), and R2 and R3 represent hydrogen atoms and the case where X represents a hydrogen atom, R1 represents a hydrogen atom, R2 represents (a) (wherein X represents a hydrogen atom), and R3 represents a methyl group are excluded. The pyrazine derivatives have a strong blood platelet agglutination depressing effect and a cyclooxygenase inhibiting effect. The above-described compounds are used as blood platelet agglutination inhibitor or anti-inflammatory agents.

  通式(I)代表的吡嗪衍生物，其中X代表氢原子、卤素原子、低级烷基、低级烷氧基或氰基，R1代表氢原子、低级烷基或(a)基团(其中X如上定义)，R2代表氢原子、卤素原子或(a)基团(其中X如上定义)，R3代表氢原子、卤素原子、低级烷基、氰基、腈基、R3 代表氢原子、卤素原子、低级烷基、氰基、萘甲基、苄基或 (b) 基团（其中 R4 代表氢原子、卤素原子或低级烷基氨基）、羧基或低级烷氧羰基，或者当 R2 和 R3 结合在一起时，R2 和 R3 与它们所结合的碳原子一起代表环己烷环或苯环，但不包括 X 代表氢原子、R 代表(a)（其中 X 代表氢原子）、R2 和 R3 代表氢原子的情况，以及 X 代表氢原子、R1 代表氢原子、R2 代表(a)（其中 X 代表氢原子）、R3 代表甲基的情况。吡嗪衍生物具有很强的血小板凝集抑制作用和环氧化酶抑制作用。上述化合物可用作血小板凝集抑制剂或抗炎剂。