5-chloro-6-methylpyrazine-2,3-dicarbonitrile | 72126-54-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-chloro-6-methylpyrazine-2,3-dicarbonitrile
• 英文别名: 2,3-Dicyano-5-chloro-6-methylpyrazine；5,6-Dichloro-2,3-dicyanopyrazine；5-chloro-6-methyl-pyrazine-2,3-dicarbonitrile
• CAS: 72126-54-6
• 化学式: C₇H₃ClN₄
• mdl: MFCD18839023
• 分子量: 178.581
• InChiKey: FMSRCHYXAOIQFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  73.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-chloro-6-methylpyrazine-2,3-dicarbonitrile 在 吡啶 、 碘 、 magnesium 、 正丁醇 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  氮酞菁：用于阳离子的红色荧光探针

  摘要：

  点亮红色的冠冕：aza [15] crown-5螯合钠和钾阳离子，可打开氮酞菁中的强红色荧光。这是由于阳离子与供体中心的配位抑制了超快分子内电荷转移。钠阳离子非常适合识别部分的腔，而钾则形成化学计量比为1：2的氮酞菁超分子组装体。

  DOI：

  10.1002/chem.201300079
• 作为产物：
  描述：

  5-甲基-6-氧代-1,6-二氢吡嗪-2,3-二甲腈 在 吡啶 、 三氯氧磷 作用下， 反应 2.0h， 生成 5-chloro-6-methylpyrazine-2,3-dicarbonitrile
  参考文献：
  名称：

  N-取代的 5-Amino-6-methylpyrazine-2,3-dicarbonitriles：微波辅助合成和生物学特性

  摘要：

  在这项工作中，一系列 15 N-苄胺取代的 5-氨基-6-甲基-吡嗪-2,3-二甲腈通过氨基脱卤反应使用微波辅助合成在实验设定和验证的条件下制备。选择这种氨基脱卤反应的方法是因为它的产率更高，反应时间更短。该反应的产物通过红外、核磁共振和其他分析数据进行表征。评估了这些化合物的抗菌、抗真菌和除草活性。化合物 3 (R = 3,4-Cl)、9 (R = 2-Cl) 和 11 (R = 4-CF3) 对结核分枝杆菌显示出良好的抗分枝杆菌活性 (MIC = 6.25 µg/mL)。发现亲脂性对于抗分枝杆菌活性很重要，并且根据克雷格图，化合物的苄基部分上的最佳取代是卤素或三氟甲基。对细菌或真菌的活性微不足道。所提出的化合物还抑制了菠菜叶绿体中的光合电子传递，活性化合物的 IC50 值在 16.4 至 487.0 µmol/L 的范围内变化。活性最高的物质是 2 (R = 3-CF3)、3 (R =

  DOI：

  10.3390/molecules19010651

文献信息

• The effect of the number of carbohydrate moieties on the azaphthalocyanine properties
  作者：Veronika Novakova、Rabia Zeynep Uslu Kobak、Radim Kučera、Kamil Kopecky、Miroslav Miletin、Veronika Krepsová、Jana Ivincová、Petr Zimcik

  DOI：10.1039/c2dt30971h

  日期：——

  A series of azaphthalocyanines (AzaPc) bearing one, two, four or eight isopropylidene-protected galactosyl units was prepared by azide–alkyne click reaction or by classical Pc template cyclotetramerization of the corresponding dicyanopyrazine and AzaPc properties important for photodynamic therapy were compared. All compounds absorbed at long wavelengths (above 650 nm) and belonged to strong singlet oxygen producers (ΦΔ = 0.58–0.64) retaining significant fluorescence emission (ΦF = 0.026–0.23). The only exception was the compound with four isopropyliden-protected galactosyl units where partial aggregation was observed. Removal of protecting groups increased the polar character of all AzaPc. However, only AzaPc bearing eight galactoses was found to be water-soluble (105 mg mL−1) but noticeably aggregated in water as well as in organic solvents (DMF, DMSO). Amphiphilic AzaPc bearing one deprotected galactose was incorporated into the lipidic bilayer of liposomes in a nonaggregated form. Liposomes may therefore be a suitable delivery system for this amphiphilic photosensitizer.

  一系列含有一个、两个、四个或八个异丙烯基保护的半乳糖基团的氮杂酞菁（AzaPc）通过叠氮-炔烃点击反应或通过相应的二氰基吡嗪的经典酞菁模板环四聚化法合成。比较了这些AzaPc在光动力治疗中重要的性质。所有化合物均在长波长（超过650 nm）处有吸收，并且是强单线态氧生产者（ΦΔ = 0.58–0.64），保留了显著的荧光发射（ΦF = 0.026–0.23）。唯一的例外是具有四个异丙烯基保护的半乳糖单位的化合物，观察到部分聚集。去除保护基团后，所有AzaPc的极性特性都增强。然而，只有含有八个半乳糖的AzaPc被发现是水溶性的（105 mg mL−1），但在水中以及有机溶剂（DMF、DMSO）中明显聚集。具有一个去保护半乳糖的两亲性AzaPc以非聚集形式被纳入了脂质体的脂双层中。因此，脂质体可能是这种两亲性光敏剂的合适递送系统。
• 2,3-Dicyanopyrazines
  申请人：Kyowa Gas Chemical Industry Co. Ltd.

  公开号：US04259489A1

  公开（公告）日：1981-03-31

  Novel 2,3-dicyanopyrazine derivatives of the formula ##STR1## wherein A represents a hydrogen atom, a lower alkyl group, an unsubstituted or substituted phenyl group, a benzyl group, or a group of the formula -ZR.sub.1 in which Z represents an oxygen or sulfur atom and R.sub.1 represents an unsubstituted or substituted lower alkyl group, a lower alkenyl group, a lower alkynyl group, an unsubstituted or substituted phenyl group, or an unsubstituted or substituted benzyl group; and B represents a halogen atom, an alkyl group containing at least 3 carbon atoms, a phenyl group having a substituent at the ortho- and/or meta-position of the benzene ring, a group of the formula ZR.sub.1 in which Z and R.sub.1 are as defined, or a group of the formula ##STR2## in which R.sub.2 and R.sub.3, independently from each other, represent a hydrogen atom, an unsubstituted or substituted lower alkyl group, a lower alkenyl group, a cycloalkyl group, an unsubstituted or substituted phenyl group, or an unsubstituted or substituted benzyl group, with the proviso that R.sub.2 and R.sub.3 do not represent a hydrogen atom at the same time, and R.sub.2 and R.sub.3 together may form a 3- to 7-membered heterocyclic ring together with the nitrogen atom to which they are bonded, said heterocyclic ring optionally containing an additional hetero atom; and processes for production thereof. These compounds have high herbicidal activity, and are useful as active ingredients of herbicides.

  2,3-二氰基吡嗪衍生物的新颖化合物，其化学式为##STR1##其中A代表氢原子、较低的烷基基团、未取代或取代的苯基团、苄基团，或者具有化学式-ZR.sub.1的基团，其中Z代表氧原子或硫原子，R.sub.1代表未取代或取代的较低烷基基团、较低烯基基团、较低炔基基团、未取代或取代的苯基团或未取代或取代的苄基团；B代表卤素原子、含有至少3个碳原子的烷基基团、苯环的邻位和/或间位有取代基的苯基团、具有已定义的Z和R.sub.1的化学式ZR.sub.1的基团，或者具有化学式##STR2##的基团，其中R.sub.2和R.sub.3分别代表氢原子、未取代或取代的较低烷基基团、较低烯基基团、环烷基基团、未取代或取代的苯基团或未取代或取代的苄基团，但R.sub.2和R.sub.3不同时代表氢原子，R.sub.2和R.sub.3共同可以与它们连接的氮原子一起形成一个3-至7-成员的杂环环，所述杂环环可选地含有一个额外的杂原子；以及其制备方法。这些化合物具有高除草活性，可用作除草剂的活性成分。
• Structural factors influencing the intramolecular charge transfer and photoinduced electron transfer in tetrapyrazinoporphyrazines
  作者：Veronika Novakova、Petr Hladík、Tereza Filandrová、Ivana Zajícová、Veronika Krepsová、Miroslav Miletin、Juraj Lenčo、Petr Zimcik

  DOI：10.1039/c3cp54731k

  日期：——

  Several structural factors were found to play a critical role in ICT efficiency. The substituent in the ortho position to the donor center significantly influences the ICT, with tert-butylsulfanyl and butoxy substituents inducing the strongest ICTs, whereas chloro, methyl, phenyl, and hydrogen substituents in this position reduce the efficiency. The strength of the donor positively influences the ICT

  合成了一系列具有一个外围连接的氨基取代基（供体）的氮杂酞菁类化合物的一系列不对称四吡嗪并卟啉（TPyzPzs），并确定了它们的光物理性质（荧光量子产率和单线态氧量子产率）。预计合成的TPyzPzs会经历分子内电荷转移（ICT），这是使它们的激发态失活的主要途径。发现一些结构性因素在ICT效率中起着至关重要的作用。在的取代基邻位的位置到供体中心显著影响ICT，与叔-丁基硫烷基和丁氧基取代基可诱导最强的ICT，而该位置的氯，甲基，苯基和氢取代基会降低效率。供体的强度对ICT效率产生积极影响，并且与TPyzPz上用作取代基的胺的氧化势相关性很好，如下所示：正丁胺< N，N-二乙胺<苯胺<吩噻嗪。TPyzPz中的ICT（具有共轭的供体和受体）也被证明比光致电子转移更强，在光电子转移中，供体和受体通过脂族连接基连接。
• [EN] SUBSTITUTED 2-(2-PHENYLHYDRAZINYL)PYRAZINE, PROCESS FOR ITS PREPARATION, ITS USE AND A PHARMACEUTICAL COMPOSITION CONTAINING THE SAME<br/>[FR] 2-(2-PHÉNYLHYDRAZINYL)PYRAZINE SUBSTITUÉE, PROCÉDÉ POUR SA PRÉPARATION, SON UTILISATION ET COMPOSITION PHARMACEUTIQUE LA CONTENANT
  申请人：UNIV KARLOVA

  公开号：WO2016095877A1

  公开（公告）日：2016-06-23

  Substituted 2-(2-phenylhydrazinyl)pyrazine of general formula I, wherein each R1, R2 is independently H or CN; R3 is CH3 or CONH2; each R4, R5, R6, R7, R8 is independently H, CI, or NO2. The invention further provides a method for preparing such substances, in which the appropriate substituted chloropyrazine is treated with a substituted phenylhydrazine under conditions of microwave synthesis. The compounds of general formula I are characterized by their low toxicity and high activity against mycobacteria. They can also be used in pharmaceutical preparations as antitubercular drugs.

  通式I的2-(2-苯基肼基)吡嗪，其中每个R1，R2独立地为H或CN; R3为CH3或CONH2; 每个R4，R5，R6，R7，R8独立地为H，CI或NO2。该发明还提供了一种制备这种物质的方法，其中适当的取代氯吡嗪在微波合成条件下与取代苯基肼反应。通式I的化合物具有低毒性和高活性对抗分枝杆菌的特点。它们还可以用于制药制剂作为抗结核药物。
• 2,3-Dicyano 6 phenyl pyrazine herbicides
  申请人：Kyowa Gas Chemical Industry Co., Ltd.

  公开号：US04460403A1

  公开（公告）日：1984-07-17

  Novel 2,3-dicyanopyrazine derivatives of the formula ##STR1## wherein A represents a hydrogen atom, a lower alkyl group, an unsubstituted or substituted phenyl group, a benzyl group, or a group of the formula --ZR.sub.1 in which Z represents an oxygen or sulfur atom and R.sub.1 represents an unsubstituted or substituted lower alkyl group, a lower alkenyl group, a lower alkynyl group, an unsubstituted or substituted phenyl group, or an unsubstituted or substituted benzyl group; and B represents a halogen atom, an alkyl group containing at least 3 carbon atoms, a phenyl group having a substituent at the ortho- and/or meta-position of the benzene ring, a group of the formula ZR.sub.1 in which Z and R.sub.1 are as defined, or a group of the formula ##STR2## in which R.sub.2 and R.sub.3, independently from each other, represent a hydrogen atom, an unsubstituted or substituted lower alkyl group, a lower alkenyl group, a cycloalkyl group, an unsubstituted or substituted phenyl group, or an unsubstituted or substituted benzyl group, with the proviso that R.sub.2 and R.sub.3 do not represent a hydrogen atom at the same time, and R.sub.2 and R.sub.3 together may form a 3- to 7-membered heterocyclic ring together with the nitrogen atom to which they are bonded, said heterocyclic ring optionally containing an additional hetero atom; and processes for production thereof. These compounds have high herbicidal activity, and are useful as active ingredients of herbicides.

  化合物2,3-二氰基吡嗪衍生物的式子为##STR1##其中A代表氢原子、较低的烷基、未取代或取代的苯基、苄基或式子--ZR.sub.1的基团，其中Z代表氧原子或硫原子，R.sub.1代表未取代或取代的较低烷基、较低烯基、较低炔基、未取代或取代的苯基或未取代或取代的苄基；B代表卤原子、含有至少3个碳原子的烷基、在苯环的邻位和/或间位有取代基的苯基、式子ZR.sub.1的基团，其中Z和R.sub.1的定义如上述，或式子##STR2##其中R.sub.2和R.sub.3独立地代表氢原子、未取代或取代的较低烷基、较低烯基、环烷基、未取代或取代的苯基或未取代或取代的苄基，但要求R.sub.2和R.sub.3不能同时代表氢原子，且R.sub.2和R.sub.3可以与它们所连接的氮原子一起形成3-至7-成员的杂环，所述杂环可以选择性地包含一个额外的杂原子；以及生产这些化合物的方法。这些化合物具有高除草活性，并且可用作除草剂的活性成分。