3-Benzyloxy-4,5-dimethoxyacetophenone | 143418-80-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-Benzyloxy-4,5-dimethoxyacetophenone
• 英文别名: 1-(3,4-Dimethoxy-5-phenylmethoxyphenyl)ethanone
• CAS: 143418-80-8
• 化学式: C₁₇H₁₈O₄
• 分子量: 286.328
• InChiKey: PWNOIOCWWVNHLR-UHFFFAOYSA-N

物化性质

• 沸点：
  418.1±40.0 °C(Predicted)
• 密度：
  1.128±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-Benzyloxy-4,5-dimethoxyacetophenone 在 甲基锂 、 copper(II) bis(trifluoromethanesulfonate) 、 三乙胺 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 2.92h， 生成 1,4-Bis(3,4-dimethoxy-5-phenylmethoxyphenyl)butane-1,4-dione
  参考文献：
  名称：

  Synthesis and PAF antagonist activity of some 2,5-diaryltetrahydrofurans incorporating PAF-like functional groups

  摘要：

  This paper describes the synthesis and structure-activity relationships of a series of 2,5-diaryltetrahydrofurans, as specific and potent antagonists at the rabbit washed platelet activating factor (PAF) receptor. The methoxyl groups in the known PAF antagonist L-652,731 were replaced with functional groups present in PAF and in the 'PAF-like' antagonists. Activity was generally retained or enhanced when one aryl ring in L-652,731 was elaborated; however incorporation of these functional groups into both of the aryl rings greatly reduced or abolished activity. These results are discussed in relation to a putative model for the PAF receptor.

  DOI：

  10.1016/0223-5234(96)89161-6
• 作为产物：
  描述：

  3,4-二甲氧基-5-苯基甲氧基苯甲酸 在 正丁基锂 、 草酰氯 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 3.25h， 生成 3-Benzyloxy-4,5-dimethoxyacetophenone
  参考文献：
  名称：

  Synthesis and PAF antagonist activity of some 2,5-diaryltetrahydrofurans incorporating PAF-like functional groups

  摘要：

  This paper describes the synthesis and structure-activity relationships of a series of 2,5-diaryltetrahydrofurans, as specific and potent antagonists at the rabbit washed platelet activating factor (PAF) receptor. The methoxyl groups in the known PAF antagonist L-652,731 were replaced with functional groups present in PAF and in the 'PAF-like' antagonists. Activity was generally retained or enhanced when one aryl ring in L-652,731 was elaborated; however incorporation of these functional groups into both of the aryl rings greatly reduced or abolished activity. These results are discussed in relation to a putative model for the PAF receptor.

  DOI：

  10.1016/0223-5234(96)89161-6

文献信息

• Antitumor compounds
  申请人：Glaxo Inc.

  公开号：US05126351A1

  公开（公告）日：1992-06-30

  The present invention relates to the compounds of formula (I), ##STR1## wherein: R.sup.1 is hydrogen, hydroxy or amino; R.sup.2 is hydrogen, hydroxy, methoxy or methoxymethoxy; R.sup.3 is hydrogen, hydroxy, amino, methoxy, methoxymethyoxy, or taken together with R.sup.2, methylenedioxy (also known as 1,3-dioxolo); R.sup.4 is hydrogen, hydroxy, methoxy, methoxymethoxy, benzyl, di(C.sub.1-4)alkylaminomethyl or, taken together with R.sup.3, methylenedioxy; R.sup.5 is hydrogen or hydroxy; provided that at least one of R.sup.1 through R.sup.5 is other than hydrogen; and i) X.sup.2 is hydroxy or methoxy with X.sup.1, X.sup.3 and X.sup.4 being hydrogen; or ii) X.sup.1 taken together with X.sup.2, X.sup.2 taken together with X.sup.3 or X.sup.3 taken together with X.sup.4, is methylenedioxy, provided that each of the remaining respective X.sup.1, X.sup.2, X.sup.3 and X.sup.4 substituents are hydrogen, intermediates in the synthesis of them, pharmaceutical formulation containing them, their use as inhibitors of topoisomerase and their use in the treatment of tumors.

  本发明涉及式(I)的化合物，其中：R.sup.1为氢、羟基或氨基；R.sup.2为氢、羟基、甲氧基或甲氧甲氧基；R.sup.3为氢、羟基、氨基、甲氧基、甲氧甲氧基，或与R.sup.2一起取代，为亚甲二氧基（也称为1,3-二氧杂环己烷）；R.sup.4为氢、羟基、甲氧基、甲氧甲氧基、苄基、二(C.sub.1-4)烷基氨甲基，或与R.sup.3一起取代，为亚甲二氧基；R.sup.5为氢或羟基；但要求R.sup.1至R.sup.5中至少有一个不是氢；i) X.sup.2为羟基或甲氧基，其中X.sup.1、X.sup.3和X.sup.4为氢；或ii) X.sup.1与X.sup.2一起取代，X.sup.2与X.sup.3一起取代，或X.sup.3与X.sup.4一起取代，为亚甲二氧基，但要求其余各自的X.sup.1、X.sup.2、X.sup.3和X.sup.4取代基为氢，它们的合成中间体，含有它们的药物配方，它们作为拓扑异构酶抑制剂的用途以及它们在肿瘤治疗中的用途。
• Substituted phenyl-1,3-dioxoloquinoline derivatives and their use as antitumor agents
  申请人：GLAXO INC.

  公开号：EP0496634A1

  公开（公告）日：1992-07-29

  The present invention relates to the compounds of formula (I), wherein:    R¹ is hydrogen, hydroxy or amino;    R² is hydrogen, hydroxy, methoxy or methoxymethoxy;    R³ is hydrogen, hydroxy, amino, methoxy, methoxymethoxy or, taken together with R², methylenedioxy (also known as 1,3 dioxolo);    R⁴ is hydrogen, hydroxy, methoxy, methoxymethoxy, benzyl, di(C₁₋₄)alkylaminomethyl or, taken together with R³, methylenedioxy;    R⁵ is hydrogen or hydroxy; provided that at least one of R¹ through R⁵ is other than hydrogen; and i) X² is hydroxy or methoxy with X¹, X³ and X⁴ being hydrogen; or ii) X¹ taken together with X²,    X² taken together with X³ or    X³ taken together with X⁴, is methylenedioxy, provided that each of the remaining respective X¹, X², X³ and X⁴ substituents are hydrogen, intermediates in the synthesis of them, pharmaceutical formulation containing them, their use as inhibitors of topoisomerase and their use in the treatment of tumors.

  本发明涉及式（I）化合物、 其中 R¹ 是氢、羟基或氨基； R² 是氢、羟基、甲氧基或甲氧基甲氧基； R³ 是氢、羟基、氨基、甲氧基、甲氧基甲氧基，或与 R² 一起是亚甲基二氧基（又称 1，3 二氧环己烷）； R⁴ 是氢、羟基、甲氧基、甲氧基甲氧基、苄基、二(C₁₋₄)烷基氨基甲基或与 R³ 结合为亚甲基二氧基； R⁵ 是氢或羟基； 但 R¹ 至 R⁵ 中至少有一个不是氢；以及 i) X² 是羟基或甲氧基，其中 X¹、X³ 和 X⁴ 是氢；或 ii) X¹ 与 X²、 X² 与 X³ 或 X¹与 X²、X²与 X³或 X³与 X⁴一起为亚甲基二氧基，条件是 X¹、X²、X³和 X⁴各自的其余取代基均为氢、 它们的合成中间体、含有它们的药物制剂、它们作为拓扑异构酶抑制剂的用途以及它们在治疗肿瘤中的用途。
• US5126351A
  申请人：——

  公开号：US5126351A

  公开（公告）日：1992-06-30
• [EN] SUBSTITUTED PHENYL-1,3 DIOXOLOQUINOLINE DERIVATIVES AND THEIR USE AS ANTITUMOR AGENTS
  申请人：GLAXO INC.

  公开号：WO1992012981A1

  公开（公告）日：1992-08-06

  (EN) The present invention relates to the compounds of formula (I), wherein: R1 is hydrogen, hydroxy or amino; R2 is hydrogen, hydroxy, methoxy or methoxymethoxy; R3 is hydrogen, hydroxy, amino, methoxy, methoxymethoxy or, taken together with R2, methylenedioxy (also known as 1,3 dioxolo); R4 is hydrogen, hydroxy, methoxy, methoxymethoxy, benzyl, di(C1-4)alkylaminomethyl or, taken together with R3, methylenedioxy; R5 is hydrogen or hydroxy; provided that at least one of R1 through R5 is other than hydrogen; and i) X2 is hydroxy or methoxy with X1, X3 and X4 being hydrogen or ii) X1 taken together with X2, X2 taken together with X3 or X3 taken together with X4, is methylenedioxy, provided that each of the remaining respective X1, X2, X3 and X4 substituents are hydrogen, intermediates in the synthesis of them, pharmaceutical formulation containing them, their use as inhibitors of topoisomerase and their use in the treatment of tumors.(FR) L'invention concerne les composés de la formule (I) dans laquelle R1 représente hydrogène, hydroxy ou amino; R2 représente hydrogène, hydroxy, méthoxy ou méthoxyméthoxy; R3 représente hydrogène, hydroxy, amino, méthoxy, méthoxyméthoxy ou, pris avec R2, méthylènedioxy (également connu sous le nom de 1,3 dioxolo); R4 représente hydrogène, hydroxy, méthoxy, méthoxyméthoxy, benzyle, di(C1-4)alkylaminométhyle ou, pris avec R3, méthylènedioxy; R5 représente hydrogène ou hydroxy; à condition que R1 et/ou R2 et/ou R3 et/ou R4 et/ou R5 soient différents de l'hydrogène; et i) X2 représente hydroxy ou méthoxy, X1, X2 et X4 représentant hydrogène; ou ii) X1 pris avec X2, X2 pris avec X3 ou X3 pris avec X4 représentent méthylènedioxy, à condition que chacun des substituants X1, X2, X3 et X4 restants respectifs représentent l'hydrogène. L'invention concerne également des intermédiaires utilisés dans la synthèse des composés précités, une formulation pharmaceutique le contenant, leur emploi comme inhibiteur de topoisomérase ainsi que leur utilisation dans le traitement des tumeurs.
• Synthesis and PAF antagonist activity of some 2,5-diaryltetrahydrofurans incorporating PAF-like functional groups
  作者：S Smith、G.J. Blackwell、D.A. Demaine、L.G. Garland、H.F. Hodson、R.M. Hyde、A.J. Parke、V.S. Rose、D.A. Sawyer、L Tilling

  DOI：10.1016/0223-5234(96)89161-6

  日期：1996.1

  This paper describes the synthesis and structure-activity relationships of a series of 2,5-diaryltetrahydrofurans, as specific and potent antagonists at the rabbit washed platelet activating factor (PAF) receptor. The methoxyl groups in the known PAF antagonist L-652,731 were replaced with functional groups present in PAF and in the 'PAF-like' antagonists. Activity was generally retained or enhanced when one aryl ring in L-652,731 was elaborated; however incorporation of these functional groups into both of the aryl rings greatly reduced or abolished activity. These results are discussed in relation to a putative model for the PAF receptor.