[3-(cyclopentyloxy)-4-methoxyphenyl]phenylmethanone | 162543-72-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [3-(cyclopentyloxy)-4-methoxyphenyl]phenylmethanone
• 英文别名: (3-Cyclopentyloxy-4-methoxyphenyl)phenylketone；3-cyclopentyloxy-4-methoxybenzophenone；3-cyclopentoxy-4-methoxybenzophenone；(3-Cyclopentyloxy-4-methoxy-phenyl)-phenyl-methanone；1-(3-cyclopentyloxy-4-methoxyphenyl)phenone；(3-cyclopentyloxy-4-methoxyphenyl)-phenylmethanone
• CAS: 162543-72-8
• 化学式: C₁₉H₂₀O₃
• 分子量: 296.366
• InChiKey: DWTPIVBPVNBBFD-UHFFFAOYSA-N

物化性质

• 沸点：
  446.2±35.0 °C(Predicted)
• 密度：
  1.138±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [3-(cyclopentyloxy)-4-methoxyphenyl]phenylmethanone 在 甲烷磺酸 、 sodium hexamethyldisilazane 作用下， 以 甲苯 为溶剂， 反应 8.0h， 生成 4-[(Z)-2-(3-cyclopentyloxy-4-methoxyphenyl)-2-phenylethenyl]pyridine
  参考文献：
  名称：

  Asymmetric Synthesis of CDP840 by Jacobsen Epoxidation. An Unusual Syn Selective Reduction of an Epoxide

  摘要：

  An asymmetric synthesis of the PDE IV inhibitor, CDP840 (3) is reported. The absolute stereochemistry was controlled by a Jacobsen epoxidation of the Z triaryl olefin 8 (89% ee) or the E triaryl olefin 9 (48% ee). The disparate results in stereocontrol were interpreted in terms of the "skewed side-on approach model" proposed by Jacobsen. LiBK4 . BH3 reduction of the epoxides was found to proceed with retention of configuration.

  DOI：

  10.1021/jo971476c
• 作为产物：
  描述：

  3-环戊氧-4-甲氧基苯甲醛 在 叔丁基过氧化氢 、 ruthenium trichloride 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 0.5h， 生成 [3-(cyclopentyloxy)-4-methoxyphenyl]phenylmethanone
  参考文献：
  名称：

  Asymmetric Synthesis of CDP840 by Jacobsen Epoxidation. An Unusual Syn Selective Reduction of an Epoxide

  摘要：

  An asymmetric synthesis of the PDE IV inhibitor, CDP840 (3) is reported. The absolute stereochemistry was controlled by a Jacobsen epoxidation of the Z triaryl olefin 8 (89% ee) or the E triaryl olefin 9 (48% ee). The disparate results in stereocontrol were interpreted in terms of the "skewed side-on approach model" proposed by Jacobsen. LiBK4 . BH3 reduction of the epoxides was found to proceed with retention of configuration.

  DOI：

  10.1021/jo971476c

文献信息

• Diphenylethylene compounds and uses thereof
  申请人：Muller W. George

  公开号：US20050107339A1

  公开（公告）日：2005-05-19

  The present invention relates to Diphenylethylene Compounds and compositions comprising a Diphenylethylene Compound. The present invention also relates to methods for preventing or treating various diseases and disorders by administering to a subject in need thereof one or more Diphenylethylene Compounds. In particular, the invention relates to methods for preventing or treating cancer or an inflammatory disorder by administering to a subject in need thereof one or more Diphenylethylene Compounds. The present invention further relates to articles of manufacture and kits comprising one or more Diphenylethylene Compounds.

  本发明涉及二苯乙烯化合物和包含二苯乙烯化合物的组合物。本发明还涉及通过向需要的受试者施用一种或多种二苯乙烯化合物来预防或治疗各种疾病和紊乱的方法。具体而言，该发明涉及通过向需要的受试者施用一种或多种二苯乙烯化合物来预防或治疗癌症或炎症性紊乱的方法。本发明还涉及包含一种或多种二苯乙烯化合物的制品和工具包。
• Immunotherapeutic agents
  申请人：Celgene Corporation

  公开号：US05929117A1

  公开（公告）日：1999-07-27

  Cyano and carboxy derivatives of substituted styrenes are inhibitors of tumor necrosis factor .alpha., nuclear factor .kappa.B, and phosphodiesterase and can be used to combat cachexia, endotoxic shock, retrovirus replication, asthma, and inflammatory conditions. A typical embodiment is 3,3-bis-(3,4-dimethoxyphenyl)acrylonitrile.

  取代苯乙烯的氰基和羧基衍生物是肿瘤坏死因子 .alpha.、核因子 .kappa.B 和磷酸二酯酶的抑制剂，可用于对抗消瘦症、内毒素休克、逆转录病毒复制、哮喘和炎症性疾病。一个典型的实施例是3,3-双-(3,4-二甲氧基苯基)丙烯腈。
• 6-phenyltetrahydro-1,3-oxazin-2-one derivative and pharmaceutical composition containing the same
  申请人：Nikken Chemicals Co., LTD

  公开号：US06251897B1

  公开（公告）日：2001-06-26

  A 6-phenyltetrahydro-1,3-oxazin-2-one derivative having the formula (I): wherein, R1 is an unsubstituted or substituted C1 to C8 alkyl group; an unsubstituted or substituted C3 to C7 cycloalkyl group;, etc., R2 is a C1 to C4 alkyl group, R3 is H; an unsubstituted or substituted C1 to C5 alkyl group; etc., R4 is H; an unsubstituted or substituted C1 to C6 alkyl group, and R5 and R6 are independently a hydrogen atom; an unsubstituted or substituted C1 to C5 alkyl group; etc. an optical isomer thereof, or a pharmacologically acceptable salt thereof, or a hydrate or a solvate thereof and pharmaceutical compositions containing the same, in particular a drug for the prevention or treatment of inflammatory diseases and a drug for asthma. The above 6-phenyltetrahydro-1,3-oxazin-2-one derivative has a strong type IV PDE inhibitory activity and has a bronchiodilator and antiinflammatory effects.

  具有以下结构式（I）的6-苯基四氢-1,3-噁嗪-2-酮衍生物：其中，R1是未取代或取代的C1至C8烷基基团；未取代或取代的C3至C7环烷基基团；等等，R2是C1至C4烷基基团，R3是H；未取代或取代的C1至C5烷基基团；等等，R4是H；未取代或取代的C1至C6烷基基团，R5和R6独立地是氢原子；未取代或取代的C1至C5烷基基团；等等。其光学异构体，或其药理学上可接受的盐，或其水合物或溶剂合物，以及含有它们的药物组合物，特别是用于预防或治疗炎症性疾病和哮喘的药物。上述6-苯基四氢-1,3-噁嗪-2-酮衍生物具有强烈的Ⅳ型磷酸二酯酶抑制活性，并具有支气管扩张剂和抗炎作用。
• Use of 2-phenylmorpholin-5-one derivatives
  申请人：Nikken Chemicals Co., Ltd.

  公开号：US06265402B1

  公开（公告）日：2001-07-24

  A 2-phenylmorpholin-5-one derivative having the formula (I): wherein R1 represents a C1 to C8 alkyl group, a C3 to C7 cycloalkyl group or an indanyl group, R2 represents a C1 to C4 alkyl group, R3 represents a hydrogen atom, a C1 to C5 alkyl group, etc., R4 represents a hydrogen atom, a C1 to C6 alkyl group, etc., R5, R6 represent a hydrogen atom, a C1 to C5 alkyl group, etc., an optical isomer thereof or a pharmacologically acceptable salt thereof, or a hydrate or solvate thereof and a pharmaceutical composition containing the same. The above compound has a strong type IV phosphodiesterase (PDE) inhibitory activity and has bronchodilater and antiinflammatory effects.

  具有以下式（I）的2-苯基吗啡啶-5-酮衍生物：其中R1代表C1至C8烷基，C3至C7环烷基或茚基，R2代表C1至C4烷基，R3代表氢原子，C1至C5烷基等，R4代表氢原子，C1至C6烷基等，R5、R6代表氢原子，C1至C5烷基等，其光学异构体或药理学上可接受的盐，或其水合物或溶剂化合物以及含有该化合物的药物组合物。上述化合物具有强烈的IV型磷酸二酯酶（PDE）抑制活性，并具有支气管扩张和抗炎作用。
• Pheynl or benzyl-substituted rolipram-based compounds for and method of
  申请人：Euro-Celtique, S.A.

  公开号：US05591776A1

  公开（公告）日：1997-01-07

  Rolipram-based PDE IV inhibitors containing phenyl- or benzyl-substituted moieties of the formula: ##STR1## wherein X.sub.1 and X.sub.2 may be the same or different and each is O or S; R.sub.1 is selected from the group consisting of hydrogen, saturated or unsaturated straight-chain or branched C.sub.2-12 alkyl groups, cycloalkyl and cycloalkyl-alkyl groups containing from 3 to 10 carbon atoms in the cycloalkyl moiety; R.sub.2 =R.sub.1 or --CH.sub.3 ; R.sub.3 is hydrogen, halogen, or a saturated or unsaturated straight-chain or branched C.sub.1-12 alkyl group, a cycloalkyl or cycloalkyl-alkyl groups containing from 3 to 7 carbon atoms in the cycloalkyl moiety; Z is a linkage selected from --CH.sub.2 CONH-- or --CH.sub.2 NHCO--, and R.sub.4 is a phenyl or benzyl which may be unsubstituted or substituted with one or more halogen atoms, alkyl groups, hydroxyl groups, cyano groups, carboxyl groups, alkoxy groups, alkoxycarbonyl, amido, carboxamido, substituted or unsubstituted amino groups, cycloalkyl and cycloalkyl-alkyl groups containing from 3 to 10 carbon atoms in the cycloalkyl moiety, aryl or aralkyl groups preferably containing from about 6 to about 10 carbon atoms, or heterocyclic groups containing nitrogen, oxygen or sulfur in the ring; the alkyl, alkoxy, cycloalkyl, cycloalkylalkyl, aryl, and aryl-alkyl groups being saturated or unsaturated, unsubstituted or substituted by halogen atoms, hydroxyl groups, cyano groups, carboxyl groups, alkoxy groups, alkoxycarbonyl, carboxamido or substituted or unsubstituted amino groups, or one or more lower alkyl groups having from 1 to 3 carbon atoms; provided that R.sub.4 cannot be substituted with more than one methoxy group. compared to theophylline or rolipram as well as with improved selectivity with regard to PDE III inhibition. Pharmaceutical compositions containing the same and methods of treatment are also disclosed.

  含有苯基或苄基取代基的Rolipram基PDE IV抑制剂的化学式为：##STR1## 其中X.sub.1和X.sub.2可以相同或不同，且每个都是O或S；R.sub.1选自氢、饱和或不饱和的直链或支链C.sub.2-12烷基、含有3-10个碳原子的环烷基和环烷基-烷基基团；R.sub.2 = R.sub.1或-CH.sub.3；R.sub.3是氢、卤素或饱和或不饱和的直链或支链C.sub.1-12烷基、含有3-7个碳原子的环烷基或环烷基-烷基基团；Z是选择自-CH.sub.2CONH-或-CH.sub.2NHCO-的连接；R.sub.4是苯基或苄基，可以是未取代或取代有一个或多个卤素原子、烷基、羟基、氰基、羧基、烷氧基、烷氧羰基、酰胺、羧酰胺、取代或未取代的氨基、含有3-10个碳原子的环烷基和环烷基-烷基基团、芳基或芳基-烷基基团，优选含有约6-10个碳原子的杂环基团，其环中含有氮、氧或硫；烷基、烷氧基、环烷基、环烷基-烷基、芳基和芳基-烷基基团是饱和或不饱和的，未取代或取代有卤素原子、羟基、氰基、羧基、烷氧基、烷氧羰基、酰胺、羧酰胺或取代或未取代的氨基，或一个或多个具有1-3个碳原子的低烷基；但R.sub.4不能取代有多于一个甲氧基。与茶碱或Rolipram相比，具有更好的PDE III抑制选择性。还公开了含有该化合物的制药组合物和治疗方法。