1-hydroxymethyl-2-oxo-3-oxabicyclo[3.1.0]hexane | 172154-27-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 1-hydroxymethyl-2-oxo-3-oxabicyclo[3.1.0]hexane
• 英文别名: 1-(hydroxymethyl)-3-oxa-bicyclo[3.1.0]hexan-2-one；(3-oxa-2-oxobicyclo[3,1,0]hexan-1-yl)methanol；1-(Hydroxymethyl)-3-oxabicyclo[3.1.0]hexan-2-one
• CAS: 172154-27-7
• 化学式: C₆H₈O₃
• 分子量: 128.128
• InChiKey: JQKCKKCEDZGBCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-hydroxymethyl-2-oxo-3-oxabicyclo[3.1.0]hexane 在 4-二甲氨基吡啶 sodium tetrahydroborate 、 甲酸 、 水 、 sodium hydride 、 potassium carbonate 、 甲基磺酰氯 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 3-{[cis-1,2-bis(hydroxymethyl)cyclopropyl]methyl}-3,9-dihydro-6-(4-methoxyphenyl)-9-oxo-5H-imidazo[1,2-a]purine
  参考文献：
  名称：

  Synthesis and biological activity of tricyclic analogues of 9-{[cis-1′,2′-bis(hydroxymethyl)cycloprop-1′-yl]methyl}guanine

  摘要：

  The base moiety of the potent antiherpetic agent 9-{[cis-1',2'-bis(hydroxymethyl)cycloprop-1'-yl]methyl}guanine 3 was transformed into that of the tricyclic 3,9-dihydro-9-oxo-6-R-5H-imidazo[1,2-a]purine system. The tricyclic analogues 5a-d were evaluated for their activity against herpes viruses as well as for cytostatic activity against HSV-1 thymidine kinase (TK) gene-transduced human osteosarcoma tumor cells. Marked activity was found against VZV. The 6-phenyl-substituted fluorescent analogues 5c and d were comparable to that of parent 3 in activity against the VZV strain YS and were 3-fold less active against the VZV strain OKA. The compounds 5a-d also showed marked activity against HSV-1 (KOS) and HSV-2 (G)-against the former generally approximately comparable to that of acyclovir la and one order of magnitude lower than 3; against the latter comparable to that of I a and approximately 6- to 30-fold lower than that of 3. The most pronounced cytostatic activity (5-fold lower than that of 3) was exhibited by compounds 5c and d. Tricyclic analogues with pseudosugar moieties are intrinsically bio-active. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.01.014
• 作为产物：
  描述：

  3-oxa-2-oxobicyclo[3,1,0]hexan-1-carbonyl chloride 在 sodium borohydrid 作用下， 以 1,4-二氧六环 为溶剂， 以15.7 mg (0.123 mmol, 26%)的产率得到1-hydroxymethyl-2-oxo-3-oxabicyclo[3.1.0]hexane
  参考文献：
  名称：

  Cyclopropane derivatives and method of preparing the same

  摘要：

  一种由化学式（I）表示的环丙烷衍生物：##STR1## 其中B代表嘌呤衍生物的基团。此外，发明的另一个方面提供了(3-氧杂-2-氧代双环[3,1,0]己烷-1-基)甲醇，以及通过用一个离去基团取代该化合物的羟基，然后与嘌呤衍生物反应来制备化学式（I）的环丙烷衍生物的方法。

  公开号：

  US05556994A1

文献信息

• QUINAZOLINE-7-ETHER COMPOUNDS AND METHODS OF USE
  申请人：Shen Wang

  公开号：US20140221406A1

  公开（公告）日：2014-08-07

  The invention provides quinazoline-7-ether derivatives, particularly 4-anilinyl-6-butenamido-quinazoline-7-ether derivatives that are inhibitors of the receptor protein tyrosine kinases (RTK). The compounds are useful in the treatment of diseases and disorders where RTK activity is implicated such as a hyperproliferative diseases (e.g., cancer). Also provided are methods of preparation of the quinazoline derivatives and methods of use as therapeutic agents alone or in a drug combination.

  这项发明提供了喹唑啉-7-醚衍生物，特别是对受体蛋白酪氨酸激酶（RTK）具有抑制作用的4-苯胺基-6-丁烯酰胺基-喹唑啉-7-醚衍生物。这些化合物在治疗RTK活性参与的疾病和紊乱方面具有用途，如高增殖性疾病（例如癌症）。还提供了制备喹唑啉衍生物的方法以及作为治疗剂单独使用或与药物组合使用的方法。
• ALKYNE SUBSTITUTED QUINAZOLINE COMPOUND AND METHODS OF USE
  申请人：Newgen Therapeutics, Inc.

  公开号：US20160031860A1

  公开（公告）日：2016-02-04

  The invention provides alkyne substituted quinazoline compounds, such as compounds of the formula (I), which are irreversible ErbB kinase inhibitors. The compounds are useful in the treatment of diseases and disorders where ErbB kinase activity is implicated such as a hyperproliferative disorder (e.g., cancer).

  这项发明提供了炔基取代的喹唑啉化合物，例如式(I)的化合物，这些化合物是不可逆的ErbB激酶抑制剂。这些化合物在治疗ErbB激酶活性参与的疾病和紊乱方面非常有用，比如高增殖性疾病（例如癌症）。
• [EN] QUINAZOLINE-7-ETHER COMPOUNDS AND METHODS OF USE<br/>[FR] COMPOSÉS DE QUINAZOLINE-7-ÉTHER ET MÉTHODES D'UTILISATION
  申请人：NEWGEN THERAPEUTICS INC

  公开号：WO2012158979A1

  公开（公告）日：2012-11-22

  The invention provides quinazoline-7-ether derivatives, particularly 4-anilinyl-6- butenamido-quinazoline-7-ether derivatives that are inhibitors of the receptor protein tyrosine kinases (RTK). The compounds are useful in the treatment of diseases and disorders where RTK activity is implicated such as a hyperproliferative diseases (e.g., cancer). Also provided are methods of preparation of the quinazoline derivatives and methods of use as therapeutic agents alone or in a drug combination.

  这项发明提供了喹唑啉-7-醚衍生物，特别是对受体蛋白酪氨酸激酶（RTK）具有抑制作用的4-苯胺基-6-丁烯酰胺基-喹唑啉-7-醚衍生物。这些化合物在治疗RTK活性参与的疾病和紊乱方面具有用途，如高增殖性疾病（例如癌症）。还提供了制备喹唑啉衍生物的方法以及作为治疗剂单独使用或与药物组合使用的方法。
• [EN] METHOD FOR PREPARING CYCLOPROPANE DERIVATIVES<br/>[FR] PROCÉDÉ DE PRÉPARATION DE DÉRIVÉS DE CYCLOPROPANE
  申请人：OKAPI SCIENCES NV

  公开号：WO2013068042A1

  公开（公告）日：2013-05-16

  The present invention relates to the preparation of cyclopropane derivatives, in particular 2- amino-9-[[(1S,2R)-1,2- bis(hydroxymethyl) cyclopropyl] methyl]-4,8-dihydro-1H-purin-6-one, especially via the [(1S,7R)-4-phenyl-3,5-dioxabicyclo[5.1.0]octan-1-yl]methanol intermediate.

  本发明涉及环丙烷衍生物的制备，特别是2-氨基-9-[[（1S,2R）-1,2-双（羟甲基）环丙基]甲基]-4,8-二氢-1H-嘌呤-6-酮，特别是通过[(1S,7R)-4-苯基-3,5-二氧杂环[5.1.0]辛-1-基]甲醇中间体。
• METHOD FOR PREPARING CYCLOPROPANE DERIVATIVES
  申请人：Kiss Eleonora

  公开号：US20150051394A1

  公开（公告）日：2015-02-19

  The present invention relates to the preparation of cyclopropane derivatives, in particular 2-amino-9-[[(1S,2R)-1,2-bis(hydroxymethyl)cyclopropyl]methyl]-4,8-dihydro-1H-purin-6-one, especially via the [(1S,7R)-4-phenyl-3,5-dioxabicyclo[5.1.0]octan-1-yl]methanol intermediate.

  本发明涉及环丙烷衍生物的制备，特别是2-氨基-9-[[（1S,2R）-1,2-双（羟甲基）环丙基]甲基]-4,8-二氢-1H-嘌呤-6-酮，尤其是通过[(1S,7R)-4-苯基-3,5-二氧杂环[5.1.0]辛-1-基]甲醇中间体。