(E)-4-(1H-imidazol-5-yl)but-3-en-2-one | 1414846-63-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (E)-4-(1H-imidazol-5-yl)but-3-en-2-one
• 英文别名: (E)-4-(1-methyl-1H-imidazol-2-yl)but-3-en-2-one；4-(1-Methyl-1H-imidazol-2-yl)but-3-en-2-one；(E)-4-(1-methylimidazol-2-yl)but-3-en-2-one
• CAS: 1414846-63-1
• 化学式: C₈H₁₀N₂O
• 分子量: 150.18
• InChiKey: SFLOSYVYOAXYGL-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-4-(1H-imidazol-5-yl)but-3-en-2-one 、 色酮-3-甲醛 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 20.0h， 以21%的产率得到3-((1E,4E)-5-(1-methyl-1H-imidazol-2-yl)-3-oxopenta-1,4-dien-1-yl)-4H-chromen-4-one
  参考文献：
  名称：

  A new class of hybrid anticancer agents inspired by the synergistic effects of curcumin and genistein: Design, synthesis, and anti-proliferative evaluation

  摘要：

  Inspired by the synergistic effects of dietary natural products with different scaffolds on the inhibition of cancer cell proliferation, incorporation of central (1E, 4E)-1,4-penta-dien-3-one linker (an optimal substitute for the central metabolically unstable diketone linker of curcumin), 1-alkyl-1H-imidazol-2-yl (a promising bioisostere of terminal aryl group in curcumin), and chromone (the common pharmacophore in genistein and quercetin) into one chemical entity resulted in ten new hybrid molecules, 3-((1E, 4E)-5-(1-alkyl-1H-imidazol-2-yl)-3-oxopenta-1,4-dien-1-yl)-4H-chromen-4-ones. They were synthesized through a three-step transformation using acid-catalyzed aldol condensation as key step. The WST-1 cell proliferation assay showed that they have greater anti-proliferative potency than curcumin, quercetin, and genistein on both androgen-dependent and androgen-independent human prostate cancer cells. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2015.08.064
• 作为产物：
  描述：

  1-甲基-1H-咪唑-2-甲醛 、 1-三苯基膦-2-丙酮 以 甲苯 为溶剂， 以98%的产率得到(E)-4-(1H-imidazol-5-yl)but-3-en-2-one
  参考文献：
  名称：

  对映选择性合成α-手性杂环的一般方法

  摘要：

  已经完成了在未保护的杂环附近的立体中心的对映选择性形成。因此，经由改性的BINOL催化剂将乙烯基硼酸加入到杂环加成的烯酮中。催化剂设计是实现一般反应的关键。对于许多常见的杂芳基，观察到高收率和有用的er。

  DOI：

  10.1021/ol3030605

文献信息

• [EN] CERTAIN CHEMICAL ENTITIES, COMPOSITIONS, AND METHODS<br/>[FR] ENTITÉS CHIMIQUES, COMPOSITIONS ET MÉTHODES PARTICULIÈRES
  申请人：NEUPHARMA INC

  公开号：WO2018035061A1

  公开（公告）日：2018-02-22

  Chemical entities that are kinase inhibitors, pharmaceutical compositions and methods of treatment of cancer are described.

  化学实体、药物组合物及其用于治疗癌症的方法，所述化学实体为激酶抑制剂。
• [EN] QUINAZOLINONE DERIVATIVES<br/>[FR] DERIVES DE QUINAZOLINONE
  申请人：CELLTECH R&D LTD

  公开号：WO2004018462A1

  公开（公告）日：2004-03-04

  A compound of formula (1): wherein: X is an oxygen or sulfur atom; R1 is an aliphatic, cycloaliphatic or cycloalkyl-alkyl-group; R2 is an optionally substituted heteroaromatic group or a -CN group; R3 is a group -(Alk1)mL1(Alk2)nR6 in which m and n, which may be the same or different, is each zero or the integer 1, Alk1 and Alk2, which may be the same or different, is each an optionally substituted aliphatic or heteroaliphatic chain, L1 is a covalent bond or a linker atom or group and R6 is a hydrogen atom or an optionally substituted cycloaliphatic, heterocycloaliphatic, aromatic or heteroaromatic group; R4 is a group -(Alk3)pL2(Alk4)qR7 in which p and q, which may be the same or different, is each zero or the integer 1, Alk3 and Alk4, which may be the same or different, is each an optionally substituted aliphatic or heteroaliphatic chain, L2 is a covalent bond or a linker atom or group and R7 is a hydrogen or halogen atom or a -CN group or an optionally substituted cycloaliphatic, heterocycloaliphatic, aromatic or heteroaromatic group; R5 is a hydrogen atom or an optionally substituted aliphatic group; and the salts, solvates, hydrates, tautomers, isomers or N-oxides thereof. The compounds of the present invention are potent inhibitors of IMPDH.

  翻译结果如下： 公式(1)的化合物：其中：X是氧原子或硫原子；R1是脂肪族、环脂肪族或环烷基-烷基团；R2是可选地取代的杂芳基团或-CN基团；R3是组-(Alk1)mL1(Alk2)nR6，其中m和n相同或不同，都是零或整数1，Alk1和Alk2相同或不同，都是可选地取代的脂肪族或杂脂肪族链，L1是共价键或连接原子或团，R6是氢原子或可选地取代的环脂肪族、杂环脂肪族、芳香族或杂芳族团；R4是组-(Alk3)pL2(Alk4)qR7，其中p和q相同或不同，都是零或整数1，Alk3和Alk4相同或不同，都是可选地取代的脂肪族或杂脂肪族链，L2是共价键或连接原子或团，R7是氢或卤素原子或-CN基团或可选地取代的环脂肪族、杂环脂肪族、芳香族或杂芳族团；R5是氢原子或可选地取代的脂肪族团；以及其盐、溶剂化物、水合物、互变异构体、同分异构体或N-氧化物。本发明的化合物是IMPDH的强效抑制剂。
• A General Method for the Enantioselective Synthesis of α-Chiral Heterocycles
  作者：Phong Q. Le、Thien S. Nguyen、Jeremy A. May

  DOI：10.1021/ol3030605

  日期：2012.12.7

  The enantioselective formation of stereocenters proximal to unprotected heterocycles has been accomplished. Thus, vinyl boronic acids are added to heterocycle-appended enones via a modified-BINOL catalyst. Catalyst design was key to enable a general reaction. High yields and useful er’s are observed for a host of common heteroaryls.

  已经完成了在未保护的杂环附近的立体中心的对映选择性形成。因此，经由改性的BINOL催化剂将乙烯基硼酸加入到杂环加成的烯酮中。催化剂设计是实现一般反应的关键。对于许多常见的杂芳基，观察到高收率和有用的er。
• CERTAIN CHEMICAL ENTITIES, COMPOSITIONS, AND METHODS
  申请人：NeuPharma, Inc.

  公开号：US20150175601A1

  公开（公告）日：2015-06-25

  Chemical entities that are kinase inhibitors, pharmaceutical compositions and methods of treatment of cancer are described.

  本文描述了一些抑制激酶的化学实体、制药组合物以及治疗癌症的方法。
• SUBSTITUTED QUINAZOLINES FOR INHIBITING KINASE ACTIVITY
  申请人：NeuPharma, Inc.

  公开号：US20170196881A1

  公开（公告）日：2017-07-13

  Chemical entities that are kinase inhibitors, pharmaceutical compositions and methods of treatment of cancer are described.