2-ethynyl-4,6-dimethoxy-1,3,5-triazine | 37968-60-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 2-ethynyl-4,6-dimethoxy-1,3,5-triazine
• CAS: 37968-60-8
• 化学式: C₇H₇N₃O₂
• 分子量: 165.151
• InChiKey: NNILPVLACKVWPE-UHFFFAOYSA-N

物化性质

• 沸点：
  305.8±25.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  57.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[2-(4-bromophenyl)-2-oxoethyl]quinolinium bromide 、 2-ethynyl-4,6-dimethoxy-1,3,5-triazine 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以52%的产率得到(4-bromophenyl)[3-(4,6-dimethoxy-1,3,5-triazin-2-yl)pyrrolo[1,2-a]quinolin-3-yl]methanone
  参考文献：
  名称：

  Discovery of indolizines containing triazine moiety as new leads for the development of antitumoral agents targeting mitotic events

  摘要：

  A new family of 3-aroylindolizines bearing a dimethoxytriazine unit in their position 1 was designed, synthesized and evaluated for their ability to inhibit tubulin polymerization and cellular growth in vitro. Compound 39 was the best candidate in the current study with a GI(50) value of 870 nM on SNB-75 CNS cancer cells and of 920 nM on MDA-MB-231/ATCC breast cancer cells. The standard NCI Compare results indicated that indolizine 39 may target PLK1 (polo-like kinase 1). (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.07.025
• 作为产物：
  描述：

  2-propynoyl chloride 、 zinc dimethyl imidodicarbonimidate 以 二氯甲烷 为溶剂， 反应 24.0h， 以55%的产率得到2-ethynyl-4,6-dimethoxy-1,3,5-triazine
  参考文献：
  名称：

  Discovery of indolizines containing triazine moiety as new leads for the development of antitumoral agents targeting mitotic events

  摘要：

  A new family of 3-aroylindolizines bearing a dimethoxytriazine unit in their position 1 was designed, synthesized and evaluated for their ability to inhibit tubulin polymerization and cellular growth in vitro. Compound 39 was the best candidate in the current study with a GI(50) value of 870 nM on SNB-75 CNS cancer cells and of 920 nM on MDA-MB-231/ATCC breast cancer cells. The standard NCI Compare results indicated that indolizine 39 may target PLK1 (polo-like kinase 1). (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.07.025

文献信息

• Synthesis and biological evaluation of a new class of triazin–triazoles as potential inhibitors of human farnesyltransferase
  作者：Liliana Lucescu、Elena Bîcu、Dalila Belei、Sergiu Shova、Benoît Rigo、Philippe Gautret、Joëlle Dubois、Alina Ghinet

  DOI：10.1007/s11164-015-2131-1

  日期：2016.3

  A new synthesis of ethynyldimethoxytriazine 1, an important platform-compound for developing new chemical entities for anticancer research and for other biological applications, is described. Compound 1 was further reacted with azides 5a–i to provide triazin–triazoles 2a–i, which were tested on human farnesyltransferase and on the NCI-60 human tumor cell lines. Synthesis of other dimethoxytriazine derivatives 15 and 16, linked to a sp 2 or a sp 3 carbon atom were also studied.

  报道了一种新型乙炔基二甲氧基三嗪1的合成方法，该化合物是开发抗癌研究和其他生物应用中新型化学实体的重要平台化合物。化合物1进一步与叠氮化合物5a–i反应，得到了三嗪-三唑2a–i，并对其在人体法呢基转移酶和NCI-60人体肿瘤细胞系中的活性进行了测试。同时，还研究了其他连接于sp2或sp3碳原子的二甲氧基三嗪衍生物15和16的合成。
• A Rational Protocol for the Synthesis of Arylated Bipyridine Ligands via a Cycloaddition Pathway
  作者：Stéphane Diring、Pascal Retailleau、Raymond Ziessel

  DOI：10.1021/jo7019866

  日期：2007.12.1

  in low yields in most cases. The use of tert-butylacetylene or N,N-dimethylamino-2-propyne, however, drives the reaction exclusively to the para isomer. Di-N,N-dibutylaminophenyl or isoquinoline ligands can also be produced in a single step by reverse Diels−Alder reactions. Cross-coupling reactions of iodo-substituted ligands or their platinum(II) complexes under Pd(0) catalysis gives branched ligands

  描述了制备各种取代的苯基-聚吡啶配体的通用设计原理。这些配体很容易通过缺电子二烯（例如2,6-二取代-1,3,4-三嗪）与乙炔基-芳烃或乙炔基-烷烃之间的区域选择性[4 + 2]环加成而制备。对于带有乙炔基没食子酸酯或乙炔基苯基二丁基氨基的富含电子的亲二烯体，发现了出色的反应性。形成两个区域异构体，由于过渡态中有利的π-π相互作用，优选间位，而在大多数情况下以低收率形成对位异构体。然而，叔丁基乙炔或N，N-二甲基氨基-2-丙炔的使用仅将反应驱动为对位异构体。二ñ，N-二丁基氨基苯基或异喹啉配体也可以通过反向Diels-Alder反应一步生成。在Pd（0）催化下，碘取代的配体或其铂（II）配合物的交叉偶联反应产生带有石蜡链，电子给体或电子受体基团的支链配体和配合物。碘官能化配体的氯-Pt（II）配合物的使用允许通过使用不同的催化剂，两个卤素都被乙炔基取代。该方法易于容纳各种功能组，并已成功地
• Exploring isoxazoles and pyrrolidinones decorated with the 4,6‐dimethoxy‐1,3,5‐triazine unit as human farnesyltransferase inhibitors
  作者：Liliana Lucescu、Alina Ghinet、Sergiu Shova、Romain Magnez、Xavier Thuru、Amaury Farce、Benoît Rigo、Dalila Belei、Joëlle Dubois、Elena Bîcu

  DOI：10.1002/ardp.201800227

  日期：2019.5

  triazinyl‐isoxazoles were afforded via an effective cycloaddition reaction between nitrile oxides and the scarcely described 2‐ethynyl‐4,6‐dimethoxy‐1,3,5‐triazine as dipolarophile. The biological evaluation of the newly synthesized compounds showed that the inhibition of human farnesyltransferase by zinc complexation could be improved with triazine‐isoxazole moieties. The replacement of the isoxazole unit

  前所未有的三嗪基-异恶唑是通过腈氧化物和几乎没有描述的作为偶极体的 2-乙炔基-4,6-二甲氧基-1,3,5-三嗪之间的有效环加成反应得到的。新合成化合物的生物学评价表明，三嗪-异恶唑部分可以改善锌络合对人法呢基转移酶的抑制。用吡咯烷-2-酮取代异恶唑单元不利于抑制活性，而吡咯烷-2-硫酮衍生物则保留了生物学潜力。还评估了所选化合物破坏 pEGFP-CAAX 转染的中国仓鼠卵巢 (CHO) 细胞中蛋白质法呢基化的潜力。
• Two New Compounds Containing Pyridinone or Triazine Heterocycles Have Antifungal Properties against Candida albicans
  作者：Laura Mena、Muriel Billamboz、Rogatien Charlet、Bérangère Desprès、Boualem Sendid、Alina Ghinet、Samir Jawhara

  DOI：10.3390/antibiotics11010072

  日期：——

  caspofungin-resistant C. albicans strains. PYR and TRI had an inhibitory effect on Candida biofilm formation and reduced the thickness of the mannan cell wall. In a Caenorhabditis elegans infection model, PYR and TRI decreased the mortality of nematodes infected with C. albicans and enhanced the expression of antimicrobial genes that promote C. albicans elimination. Overall, PYR and TRI showed antifungal properties

  由机会性酵母白色念珠菌引起的念珠菌病是当今最常见的真菌感染。在过去十年中出现了白色念珠菌对当前抗真菌药物的耐药性，导致需要新型抗真菌药物。我们的目标是通过文库筛选方法选择新的抗真菌化合物，并评估它们对白色念珠菌的抗真菌作用。从化学文库 JUNIA 中筛选出 90 种潜在的抗真菌化合物后，得到两种化合物，1-(4-chlorophenyl)-4-((4-chlorophenyl)amino)-3,6-dimethylpyridin-2(1H)-one (PYR) (Z)-N-(2-(4,6-dimethoxy-1,3,5-triazin-2-yl)vinyl)-4-methoxyaniline (TRI) 被鉴定为具有潜在的抗真菌活性。用 PYR 和 TRI 处理导致白色念珠菌生物发光以及真菌菌落数量显着减少，表明快速的杀菌活性。这两种化合物对临床分离的氟康唑或卡泊芬净耐药的白色念珠菌菌株也