1,3-dioxo-2-phenyl-2,3,5,8-tetrahydro-1H-[1,2,4]triazolo[1,2-a]pyridazine-5-carboxylic acid | 62221-98-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,3-dioxo-2-phenyl-2,3,5,8-tetrahydro-1H-[1,2,4]triazolo[1,2-a]pyridazine-5-carboxylic acid
• 英文别名: 1,3-Dioxo-2-phenyl-2,3,5,8-tetrahydro-1H-[1,2,4]triazolo[1,2-a]pyridazine-5-carboxylic acid；1,3-dioxo-2-phenyl-5,8-dihydro-[1,2,4]triazolo[1,2-a]pyridazine-5-carboxylic acid
• CAS: 62221-98-1
• 化学式: C₁₃H₁₁N₃O₄
• 分子量: 273.248
• InChiKey: FLGDWPFFEFODOV-UHFFFAOYSA-N

物化性质

• 熔点：
  216-220 °C(Solv: water (7732-18-5); ethanol (64-17-5))
• 沸点：
  447.8±55.0 °C(Predicted)
• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  81.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3-dioxo-2-phenyl-2,3,5,8-tetrahydro-1H-[1,2,4]triazolo[1,2-a]pyridazine-5-carboxylic acid 、 3-hydroxy-28-[(tetrahydro-2H-pyran-2-yl)oxy]lup-20(29)-ene 在 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 24.0h， 以50%的产率得到
  参考文献：
  名称：

  WO2007/141389

  摘要：

  公开号：
• 作为产物：
  描述：

  4-苯基脲唑 在 次氯酸叔丁酯 作用下， 以 乙酸乙酯 为溶剂， 反应 18.58h， 生成 1,3-dioxo-2-phenyl-2,3,5,8-tetrahydro-1H-[1,2,4]triazolo[1,2-a]pyridazine-5-carboxylic acid
  参考文献：
  名称：

  1-Azafagomine: A Hydroxyhexahydropyridazine That Potently Inhibits Enzymatic Glycoside Cleavage

  摘要：

  Abstract(3,4‐trans‐4,5‐trans)‐4,5‐dihydroxy‐3‐hydroxymethylhexahydropyrida‐zine (16) was synthesized in four steps from 2,4‐pentadienol (22) and 4‐phenyl‐triazolin‐3,5‐dione (18) in an overall yield of 32%. In the first step a Diels‐Alder reaction between 18 and 22 gave (π)‐2‐hydroxymethyl‐8‐phenyl‐1,6,8‐triazabicyclo[4.3.0]non‐3‐ene‐7,9‐dione (23c) in 88% yield. Epoxidation of 23c with trifluoromethyl(methyl)dioxirane, generated in situ, gave the trans epoxide 24c in 62% yield. Hydrolysis of the epoxide with perchloric acid gave stereoselectively (2,3‐trans‐3,4‐trans)‐3,4‐dihydroxy‐2‐hydroxy‐methyl‐8‐phenyl‐1,6,8‐triazabicyclo[4.3.0]‐nonane‐7,9‐dione (26) in 73% yield. In the fourth and final step, hydrazinolysis of 26 gave 16 in 84% yield. Pyridazine 16 was found to be a potent inhibitor of α‐and β‐glucosidase, isomaltase and glyco‐gen phosphorylase, while galactosidases and α‐mannosidase were not inhibited. The inhibition of β‐glucosidase is independent of pH, and was found to be due to unprotonated 16.

  DOI：

  10.1002/chem.19970030616

文献信息

• Highly efficient and versatile synthesis of libraries of constrained β-strand mimetics
  作者：Cyprian O. Ogbu、Maher N. Qabar、P.Douglas Boatman、Jan Urban、Joseph P. Meara、Mark D. Ferguson、John Tulinsky、Chris Lum、Suresh Babu、Mark A. Blaskovich、Hiroshi Nakanishi、Fuqiang Ruan、Bolong Cao、Ryan Minarik、Tom Little、Sherry Nelson、Minh Nguyen、Anna Gall、Michael Kann

  DOI：10.1016/s0960-894x(98)00420-x

  日期：1998.9

  superfamily of enzymes has been investigated. The Diels Alder cycloaddition reaction on solid support has been found to be highly efficient for the synthesis of libraries of compounds that mimic the beta-strand secondary structure of proteins. Several potent and selective inhibitors of proteases have been discovered.

  已经研究了使用双环模板产生酶的蛋白酶超家族的抑制剂的一般方法。已经发现在固体载体上的狄尔斯-阿尔德环加成反应对于合成模拟蛋白质的β链二级结构的化合物的文库是高效的。已经发现了几种有效的和选择性的蛋白酶抑制剂。
• BETULIN DERIVED COMPOUNDS USEFUL AS ANTIPROTOZOAL AGENTS
  申请人：Yli-Kauhaluoma Jari

  公开号：US20100190795A1

  公开（公告）日：2010-07-29

  The invention relates to betulin derivatives, and to the use thereof as agents against protozoa of the genus Leishmania and against leishmaniasis in applications of pharmaceutical industry.

  该发明涉及到白桦酸衍生物，并将其用作制药工业中针对副单胞菌属Leishmania及利什曼病的药剂。
• BETULIN DERIVED COMPOUNDS USEFUL AS ANTIBACTERIAL AGENTS
  申请人：Yli-Kauhaluoma Jari

  公开号：US20100273801A1

  公开（公告）日：2010-10-28

  The invention relates to compouns derived from betulin, and to the use thereof as antibacterial agents in pharmaceutical and cosmetic applications.

  本发明涉及从白桦酸衍生的化合物，并将其用作医药和化妆品应用中的抗菌剂。
• [EN] BETULIN DERIVED COMPOUNDS USEFUL AS ANTIBACTERIAL AGENTS<br/>[FR] COMPOSÉS DÉRIVÉS DE BÉTULINE UTILES EN TANT QU'AGENTS ANTIBACTÉRIENS
  申请人：VALTION TEKNILLINEN

  公开号：WO2007141389A1

  公开（公告）日：2007-12-13

  [EN] The invention relates to compouns derived from betulin, and to the use thereof as antibacterial agents in pharmaceutical and cosmetic applications.
  [FR] La présente invention concerne des composés dérivés de la bétuline, et l'utilisation de ceux-ci en tant qu'agents antibactériens dans des applications pharmaceutiques et cosmétiques.
• [EN] COMPOSITIONS COMPRISING BETULONIC ACID<br/>[FR] COMPOSITIONS COMPRENANT DE L'ACIDE BÉTULONIQUE
  申请人：VALTION TEKNILLINEN

  公开号：WO2007141392A2

  公开（公告）日：2007-12-13

  [EN] The invention relates to compositions of cosmetic and pharmaceutical industries comprising betulonic acid for humans and animals, and further, to the use of betulonic acid in compositions of cosmetic and pharmaceutical industries. The invention is also directed to compositions containing, besides betulonic acid, optionally other compounds derived from betulin.
  [FR] La présente invention concerne des compositions des industries cosmétique et pharmaceutique comprenant de l'acide bétulonique pour des humains et des animaux, et en outre, l'utilisation d'acide bétulonique dans des compositions des industries cosmétique et pharmaceutique. L'invention concerne en outre des compositions contenant, hormis l'acide bétulonique, facultativement d'autres composés dérivés de la bétuline.