4-Methyl-3-phenacylthiazolium bromide | 6274-00-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-Methyl-3-phenacylthiazolium bromide
• 英文别名: 3-(2-Phenyl-2-oxoaethyl)-4-methylthiazolium-Kation；N-Phenacyl-4-methyl-thiazolin；4-methyl-3-(2-oxo-2-phenylethyl)thiazol-3-ium bromide；4-methyl-3-(2-oxo-2-phenyl-ethyl)-thiazolium; bromide；3-(2-phenyl-2-oxoethyl)-4-methylthiazolium bromide；4-Methyl-3-(2-oxo-2-phenylethyl)-1,3-thiazol-3-ium bromide；2-(4-methyl-1,3-thiazol-3-ium-3-yl)-1-phenylethanone;bromide
• CAS: 6274-00-6
• 化学式: Br*C₁₂H₁₂NOS
• 分子量: 298.203
• InChiKey: FJNLZJRANZQMNW-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.77
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  49.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Methyl-3-phenacylthiazolium bromide 生成 1-(cis-2-carboxy-vinyloxy)-4-methyl-1-phenyl-1H-pyrrolo[2,1-c][1,4]thiazine-7-carboxylic acid
  参考文献：
  名称：

  Bridgehead nitrogen systems. X. Cycloadditions with thiazolium N-ylides

  摘要：

  DOI：

  10.1021/jo00864a002
• 作为产物：
  描述：

  4-甲基噻唑 、 2-溴苯乙酮 以 乙酸乙酯 为溶剂， 反应 0.5h， 以81%的产率得到4-Methyl-3-phenacylthiazolium bromide
  参考文献：
  名称：

  多取代N稠合杂环的合成及其对Hep-G2癌细胞系的抗增殖活性

  摘要：

  摘要一锅法通过相应的咪唑鎓碘化物和噻唑鎓碘化物与烯烃的[3 + 2]环加成反应，然后氧化将吡咯并[1,2- a ]咪唑和吡咯并[2,1- b ]噻唑衍生物合成在轻度氧化剂四重吡啶吡啶钴（II）重铬酸盐的作用下，一级环加合物的芳构化。通过MTT法检测了14个新的双环N-稠合杂环对人肝细胞肝癌（Hep-G2）细胞的抗增殖活性。一些化合物显示出良好的抗增殖活性，尤其是化合物3i显示出强大的抗增殖活性，IC 50值为0.36μg/ cm 3。 图形概要

  DOI：

  10.1007/s00706-011-0469-7

文献信息

• Crosslink Breakers for Preservation of Biological Substances
  申请人：Spiegel David

  公开号：US20150099260A1

  公开（公告）日：2015-04-09

  A preservative for body fluids, proteins, cells and tissues comprising an effective amount of an AGE crosslink breaker for preventing formation of advanced glycation end products. The AGE crosslink breaker comprises a compound of Structure (1): wherein V, W, X, Y and Z are any atom suitable for a heterocyclic carbene or carbene precursor framework, including B, C, O, N, S, Se, P, and As in any chemically-feasible oxidation state; wherein Q, R, M, T and U are any atom or substituent, including but not limited to, H, CL n , NL n , PL n , OL n , SL n , SeL n , L n Cl, L n Br, L n I, wherein L is any atom, substituent or group, and n is any integer such that Q, R, M, T, and U can access all chemically-feasible oxidation states; and wherein G comprises any charged counter ion including, but not limited to those derived from C, O, N, B, Al, S, Se, Cl, Br, I in any chemically-feasible oxidation state.

  一种用于体液、蛋白质、细胞和组织的防腐剂，包括一种有效量的AGE交联断裂剂，用于预防高级糖基化终产物的形成。AGE交联断裂剂包括结构（1）中的化合物： 其中V、W、X、Y和Z是适用于杂环卡宾或卡宾前体框架的任何原子，包括B、C、O、N、S、Se、P和As在任何化学上可行的氧化态； 其中Q、R、M、T和U是任何原子或取代基，包括但不限于H、CLn、NLn、PLn、OLn、SLn、SeLn、LnCl、LnBr、LnI，其中L是任何原子、取代基或基团，n是任何整数，使得Q、R、M、T和U可以访问所有化学上可行的氧化态；以及 其中G包括任何带电的对离子，包括但不限于那些来源于C、O、N、B、Al、S、Se、Cl、Br、I在任何化学上可行的氧化态。
• Method for treating fibrotic diseases or other indications IC
  申请人：Alteon, Inc.

  公开号：US20020068729A1

  公开（公告）日：2002-06-06

  Provided, among other things, is a method of treating or ameliorating or preventing an indication of the invention in an animal, including a human comprising administering an effective amount of a compound of the formula I: 1

  提供了一种处理、改善或预防动物包括人类发明的指示的方法，包括给予公式I的化合物的有效量：1
• 3-deoxyglucosone and skin
  申请人：——

  公开号：US20030219440A1

  公开（公告）日：2003-11-27

  The invention relates to a method of removing 3-deoxyglucosone and other alpha-dicarbonyl sugars from skin. The invention further relates to methods of inhibiting production and function of 3-deoxyglucosone and other alpha-dicarbonyl sugars in skin. The invention also relates to methods of treating 3-deoxyglucosone and other alpha-dicarbonyl sugars associated diseases and disorders of skin.

  该发明涉及一种从皮肤中去除3-去氧葡萄糖酮和其他α-二酮糖的方法。该发明还涉及抑制皮肤中3-去氧葡萄糖酮和其他α-二酮糖的产生和功能的方法。该发明还涉及治疗与皮肤相关的3-去氧葡萄糖酮和其他α-二酮糖相关疾病和障碍的方法。
• Reinvestigation of reactions of thiazolium and benzothiazolium N-phenacylides with electron-deficient acetylenes
  作者：Tatsunori Iwamura、Masahiro Kobayashi、Takashi Ichikawa、Hiroshi Shimizu、Tadashi Kataoka

  DOI：10.1039/p19960000629

  日期：——

  Reactions of thiazolium and benzothiazolium N-phenacylides with dimethyl acetylenedicarboxylate (DMAD) have been reexamined. The thiazolium N-phenacylides 5, generated in situ from 4-methyl- or 5-phenyl-3-phenacylthiazolium bromides 13 with triethylamine, reacted with DMAD in dry DMF to give the thiazole ring-opened products 15, in which two molecules of DMAD had been incorporated. The reactions when conducted in both aqueous DMF and in dry DMF in the presence of lithium perchlorate gave the hemithioacetals 6 which could be transformed into the 1 : 2 reaction products 15 of the ylides and DMAD. Benzothiazolium N-phenacylides 8 similarly reacted with DMAD to afford the 1 : 2 reaction products 19 or the hemithioacetals 20. The reaction mechanism is discussed.

  噻唑鎓和苯并噻唑鎓N-苯甲酰甲酯与二甲基乙炔二羧酸酯（DMAD）的反应已重新研究。噻唑鎓N-苯甲酰甲酯5，由4-甲基或5-苯基-3-苯甲酰甲基噻唑鎓溴13与三乙胺现场生成，与DMAD在无水DMF中反应生成噻唑环开环产物15，其中嵌入了两个DMAD分子。在水合DMF和无水DMF中加入高氯酸锂进行的反应得到半硫缩醛6，这些半硫缩醛可以转化为亚胺和DMAD的1:2反应产物15。苯并噻唑鎓N-苯甲酰甲酯8同样与DMAD反应，得到1:2反应产物19或半硫缩醛20。对反应机理进行了讨论。
• Methods of Treating or Preventing Cardiac Disease Associated With a High Fat Diet
  申请人：Thomas Merlin

  公开号：US20090088461A1

  公开（公告）日：2009-04-02

  The present invention relates to a method of treating or preventing cardiac disorders, myocardial inflammation or myocardial oxidative stress associated with a high fat diet or in a patient subjected to a high fat diet using the thiazolium compounds and compositions of the invention. The present invention also relates to a method of ameliorating weight gain, myocardial AGE accumulation associated, mitochondrial superoxide production, RAGE expression or PPARα expression with a high fat diet or in a patient subjected to a high fat diet using the thiazolium compounds and compositions of the invention.

  本发明涉及一种使用该发明的噻唑类化合物和组合物治疗或预防与高脂饮食相关的心脏疾病、心肌炎症或心肌氧化应激的方法。本发明还涉及一种使用该发明的噻唑类化合物和组合物改善与高脂饮食相关的体重增加、心肌AGE积累、线粒体超氧化物产生、RAGE表达或PPARα表达的方法。