(+/-)-3-Methyl-5-phenyl-5H-thiazolo[2,3-b]quinazoline | 152302-59-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: (+/-)-3-Methyl-5-phenyl-5H-thiazolo[2,3-b]quinazoline
• 英文别名: Heterocyclic antiatherosclerotic agent；3-methyl-5-phenyl-5H-[1,3]thiazolo[2,3-b]quinazoline
• CAS: 152302-59-5
• 化学式: C₁₇H₁₄N₂S
• 分子量: 278.378
• InChiKey: DSEYBGDEFWSNEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-3-Methyl-5-phenyl-5H-thiazolo[2,3-b]quinazoline 生成 (R)-3-Methyl-5-phenyl-5H-thiazolo[2,3-b]quinazoline
  参考文献：
  名称：

  An efficient synthesis of enantiopure SDZ 267–489 via a resolution/racemization method

  摘要：

  A new synthesis of (R)-3-methyl-5-phenyl-5H-thiazolo[2,3-b]quinazoline 1, a serum HDL cholesterol raising agent, is described utilizing a resolution of the racemic compound with D-tartaric acid. The undesired S-enantiomer was recycled using either a photochemical or thermal electrocyclic ring opening/closing reaction making the synthesis economical. (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00070-5
• 作为产物：
  描述：

  (2-氨基苯基)(苯基)甲醇 在 盐酸 、 sodium bromide 作用下， 以 乙醇 、 异丙醇 为溶剂， 反应 5.0h， 生成 (+/-)-3-Methyl-5-phenyl-5H-thiazolo[2,3-b]quinazoline
  参考文献：
  名称：

  An efficient synthesis of enantiopure SDZ 267–489 via a resolution/racemization method

  摘要：

  A new synthesis of (R)-3-methyl-5-phenyl-5H-thiazolo[2,3-b]quinazoline 1, a serum HDL cholesterol raising agent, is described utilizing a resolution of the racemic compound with D-tartaric acid. The undesired S-enantiomer was recycled using either a photochemical or thermal electrocyclic ring opening/closing reaction making the synthesis economical. (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00070-5

文献信息

• Antiatherosclerotic substituted phenylquinazoline derivatives
  申请人：SANDOZ LTD.

  公开号：EP0564397A1

  公开（公告）日：1993-10-06

  The invention relates to substituted phenylquinazoline derivatives. It concerns the compounds of formula I wherein the substituents have various significances. They may be obtained by a process comprising dehydration, ring closure and/or alkylation, and optional recovery in racemic or optically active, in free base or acid addition salt form. They possess pharmacological activity, in particular,they raise the blood serum high density lipoprotein level and are thus indicated for use in the treatment of atherosclerosis.

  本发明涉及取代苯基喹唑啉衍生物。它涉及式I的化合物，其中取代基具有不同的意义。它们可以通过脱水、环闭和/或烷基化的过程获得，并可以在外消旋或光学活性、自由碱或酸盐形式中进行回收。它们具有药理活性，特别是能提高血清高密度脂蛋白水平，因此适用于动脉硬化的治疗。
• QUINAZOLINE DERIVATIVES, PROCESS FOR THEIR PREPARATION, THEIR USE AS ANTIMITOTICS AND PHARMACEUTICAL COMPOSITIONS COMPRISING SAID DERIVATIVES
  申请人：EMBL

  公开号：EP1807402A1

  公开（公告）日：2007-07-18
• JPH0649076A
  申请人：——

  公开号：JPH0649076A

  公开（公告）日：1994-02-22
• [EN] QUINAZOLINE DERIVATIVES, PROCESS FOR THEIR PREPARATION, THEIR USE AS ANTIMITOTICS AND PHARMACEUTICAL COMPOSITIONS COMPRISING SAID DERIVATIVES<br/>[FR] DERIVES DE QUINAZOLINE, PROCEDE DE PREPARATION, UTILISATION COMME ANTIMITOTIQUES ET COMPOSITIONS PHARMACEUTIQUES CONTENANT CES DERIVES
  申请人：EMBL

  公开号：WO2006048308A1

  公开（公告）日：2006-05-11

  [EN] The invention relates to quinazoline derivatives of formula (I), in which R¹, X and A have the meanings as indicated, or to a pharmaceutically acceptable salt thereof, e.g. (formula II). Such compounds are useful as modulators, in particular inhibitors, of the mitotic kinesin Eg5. i.e. the human protein (also called KSP), the Xenopus laevis homologue, further homologues from other species as well as allelic variants and functionally related proteins. The invention also relates to processes for their preparation, pharmaceutical compositions comprising said quinazoline derivatives, and the use of said quinazoline derivatives, in particular for treating diseases such as cancer.
  [FR] L'invention concerne des dérivés de quinazoline représentés par la formule (I), dans laquelle R¹, X et A sont tels que représentés dans le descriptif, ou un sel pharmaceutiquement acceptable de ceux-ci, par exemple (formule II). Ces composés sont utilisés comme modulateurs, en particulier comme inhibiteurs, de la kinésine mitotique Eg5, à savoir la protéine humaine (également appelée KSP), l'homologue de Xenopus laevis, d'autres homologues provenant d'autres espèces ainsi que des variants alléliques et des protéines fonctionnellement apparentées. Par ailleurs, l'invention concerne des procédés de préparation de ces dérivés de quinazoline, des compositions pharmaceutiques contenant ces dérivés de quinazoline, ainsi que l'utilisation de ces dérivés de quinazoline, en particulier pour traiter des maladies telles que le cancer.
• An efficient synthesis of enantiopure SDZ 267–489 via a resolution/racemization method
  作者：Daqiang Xu、Paul G. Mattner、Andrew Kucerovy、Kapa Prasad、Oljan Repic

  DOI：10.1016/0957-4166(96)00070-5

  日期：1996.3

  A new synthesis of (R)-3-methyl-5-phenyl-5H-thiazolo[2,3-b]quinazoline 1, a serum HDL cholesterol raising agent, is described utilizing a resolution of the racemic compound with D-tartaric acid. The undesired S-enantiomer was recycled using either a photochemical or thermal electrocyclic ring opening/closing reaction making the synthesis economical. (C) 1996 Elsevier Science Ltd