3-乙基-6-甲氧基-5-甲基-2-[2-[(3E)-3-甲基-4-苯基-3-丁烯-1-基]-4-恶唑基]-4H-吡喃-4-酮 | 134332-63-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 中文名称: 3-乙基-6-甲氧基-5-甲基-2-[2-[(3E)-3-甲基-4-苯基-3-丁烯-1-基]-4-恶唑基]-4H-吡喃-4-酮
• 英文名称: phenoxan
• 英文别名: 5-ethyl-2-methoxy-3-methyl-6-[2-[(E)-3-methyl-4-phenylbut-3-enyl]-1,3-oxazol-4-yl]pyran-4-one
• CAS: 134332-63-1
• 化学式: C₂₃H₂₅NO₄
• 分子量: 379.456
• InChiKey: OFVMLCJEDYAOIB-FYWRMAATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-甲基-4-恶唑甲醇 在 吡啶 、 正丁基锂 、 草酰氯 、 叔丁基二甲硅基三氟甲磺酸酯 、 对甲苯磺酸 、 二甲基亚砜 、 六甲基二硅氮烷 、 lithium diisopropyl amide 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 9.33h， 生成 3-乙基-6-甲氧基-5-甲基-2-[2-[(3E)-3-甲基-4-苯基-3-丁烯-1-基]-4-恶唑基]-4H-吡喃-4-酮
  参考文献：
  名称：

  一种取代4-羟基吡喃-2-酮的方法：苯氧杂酚的全合成。

  摘要：

  DOI：

  10.1021/jo960221g

文献信息

• Total synthesis of phenoxan and a related pyrone derivative
  作者：Yasuharu Ishibashi、Shigeru Ohba、Shigeru Nishiyama、Shosuke Yamamura

  DOI：10.1016/0040-4039(96)00483-2

  日期：1996.4

  Phenoxan, HIV-1 inhibitor isolated from the myxobacteria, has been synthesized in 16 steps starting from ethyl 2-methylacetoacetate. The related isomer corresponding to the oxazole part was also obtained via an orthoester-enediol rearrangement.

  从粘细菌分离出的HIV-1抑制剂Phenoxan从2-甲基乙酰乙酸乙酯开始分16步合成。还通过原酸酯-烯二醇重排获得对应于恶唑部分的相关异构体。
• CANCER TREATMENT BY SIMULTANEOUS TARGETING ENERGY METABOLISM AND INTRACELLULAR PH
  申请人：Deutsches Krebsforschungszentrum

  公开号：EP3471713A1

  公开（公告）日：2019-04-24
• Cancer Treatment by Simultaneous Targeting Energy Metabolism and Intracellular pH
  申请人：Deutsches Krebsforschungszentrum

  公开号：US20190321311A1

  公开（公告）日：2019-10-24

  The present invention relates to an inhibitor of mitochondrial respiration for use in treatment of cancer with a proton ionophore and relates to a proton ionophore for use in treatment of cancer with an inhibitor of mitochondrial respiration. The present invention further relates to a combined preparation for simultaneous, separate or sequential use comprising (i) an inhibitor of mitochondrial respiration and (ii) a proton ionophore, to said combined preparation for use in treatment of cancer, and to kits and methods related thereto.
• [EN] CANCER TREATMENT BY SIMULTANEOUS TARGETING ENERGY METABOLISM AND INTRACELLULAR PH<br/>[FR] TRAITEMENT DU CANCER PAR CIBLAGE SIMULTANÉ DU MÉTABOLISME ÉNERGÉTIQUE ET DU PH INTRACELLULAIRE
  申请人：DEUTSCHES KREBSFORSCH

  公开号：WO2017216257A1

  公开（公告）日：2017-12-21

  The present invention relates to an inhibitor of mitochondrial respiration for use in treatment of cancer with a proton ionophore and relates to a proton ionophore for use in treatment of cancer with an inhibitor of mitochondrial respiration. The present invention further relates to a combined preparation for simultaneous, separate or sequential use comprising (i) an inhibitor of mitochondrial respiration and (ii) a proton ionophore, to said combined preparation for use in treatment of cancer, and to kits and methods related thereto.
• [EN] COMBINATION TREATMENT OF CANCER TARGETING ENERGY METABOLISM AND INTRACELLULAR PH<br/>[FR] TRAITEMENT COMBINÉ CONTRE LE CANCER CIBLANT LE MÉTABOLISME ÉNERGÉTIQUE ET LE PH INTRACELLULAIRE
  申请人：DEUTSCHES KREBSFORSCH

  公开号：WO2020234454A1

  公开（公告）日：2020-11-26

  The present invention relates to a compound causing a decrease of intracellular pH for use in treatment of cancer with an inhibitor of mitochondrial respiration and a proton ionophore; to a proton ionophore for use in treatment of cancer with an inhibitor of mitochondrial respiration and a compound causing a decrease of intracellular pH; and to an inhibitor of mitochondrial respiration for use in treatment of cancer with a proton ionophore and a compound causing a decrease of intracellular pH. The present invention also relates to a combined preparation for simultaneous, separate or sequential use comprising (i) a compound causing a decrease of intracellular pH, (ii) an inhibitor of mitochondrial respiration, and (iii) a proton ionophore, and to a method for determining whether a subject suffering from cancer is susceptible to a combined treatment comprising administration of a compound causing a decrease of intracellular pH, an inhibitor of mitochondrial respiration, and a proton ionophore related thereto.