rac-(2S,3S)-6-hydroxy-2-(3,4-dimethoxyphenyl)-3-methyl-5-propyl-2,3-dihydrobenzofuran | 104832-94-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: rac-(2S,3S)-6-hydroxy-2-(3,4-dimethoxyphenyl)-3-methyl-5-propyl-2,3-dihydrobenzofuran
• 英文别名: (2S,3S)-2-(3,4-Dimethoxy-phenyl)-3-methyl-5-propyl-2,3-dihydro-benzofuran-6-ol；(2S,3S)-2-(3,4-dimethoxyphenyl)-3-methyl-5-propyl-2,3-dihydro-1-benzofuran-6-ol
• CAS: 104832-94-2
• 化学式: C₂₀H₂₄O₄
• 分子量: 328.408
• InChiKey: SNLONBFXAGUAFN-YUNKPMOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  lead(IV) acetate 、 rac-(2S,3S)-6-hydroxy-2-(3,4-dimethoxyphenyl)-3-methyl-5-propyl-2,3-dihydrobenzofuran 在 二氯甲烷 、 silica gel 、 ethyl acetate n-hexane 、 acetates 作用下， 以 甲醇 为溶剂， 反应 1.5h， 生成 3a-Acetoxy-2-(3,4-dimethoxyphenyl)-3-methyl-5-n-propyl-2,3,3a,6-tetrahydro-6-oxo-benzofuran
  参考文献：
  名称：

  Substituted 2,3,3a,6-tetrahydro-6-oxobenzofuran derivative useful as PAF

  摘要：

  已经制备了取代的2,3,3a,6-四氢-6-氧代苯并呋喃衍生物。这些新木脂素具有强效和特异性的PAF（血小板活化因子）拮抗活性，因此在治疗各种由PAF介导的疾病或疾病中有用，例如疼痛，发热，炎症，心血管疾病，哮喘，肺水肿，过敏性疾病，皮肤病，牛皮癣，毒性休克综合征和成人呼吸窘迫综合征。

  公开号：

  US04704462A1
• 作为产物：
  描述：

  (E)-3-(3,4-二甲氧基苯基)烯丙醇 在 palladium on activated charcoal 氢气 、 三苯基膦 、 N,N-二乙基苯胺 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 25.0~225.0 ℃ 、137.9 kPa 条件下， 反应 15.0h， 生成 rac-(2S,3S)-6-hydroxy-2-(3,4-dimethoxyphenyl)-3-methyl-5-propyl-2,3-dihydrobenzofuran
  参考文献：
  名称：

  Structure-activity relationships of kadsurenone analogues

  摘要：

  Kadsurenone, a specific receptor antagonist of platelet-activating factor (PAF), and its analogues were prepared from derivatives of cinnamyl alcohol and (allyloxy)phenol. Racemic kadsurenone, resolvable by a Chiralpak column at low temperatures, has an IC50 value of 2 X 10(-7) M, which is about 50% of the activity of the natural product (IC50 = 1 X 10(-7) M). The structural specificity of kadsurenone was further demonstrated by the low PAF-receptor-blocking activities of denudatin B, mirandin A, desallylkadsurenone, and the 2-epimer of kadsurenone.

  DOI：

  10.1021/jm00384a023

文献信息

• US4704462A
  申请人：——

  公开号：US4704462A

  公开（公告）日：1987-11-03
• Structure-activity relationships of kadsurenone analogues
  作者：Mitree M. Ponpipom、Robert L. Bugianesi、David R. Brooker、Bao-zhen Yue、San-bao Hwang、Tsung-ying Shen

  DOI：10.1021/jm00384a023

  日期：1987.1

  Kadsurenone, a specific receptor antagonist of platelet-activating factor (PAF), and its analogues were prepared from derivatives of cinnamyl alcohol and (allyloxy)phenol. Racemic kadsurenone, resolvable by a Chiralpak column at low temperatures, has an IC50 value of 2 X 10(-7) M, which is about 50% of the activity of the natural product (IC50 = 1 X 10(-7) M). The structural specificity of kadsurenone was further demonstrated by the low PAF-receptor-blocking activities of denudatin B, mirandin A, desallylkadsurenone, and the 2-epimer of kadsurenone.
• Substituted 2,3,3a,6-tetrahydro-6-oxobenzofuran derivative useful as PAF
  申请人：Merck & Co., Inc.

  公开号：US04704462A1

  公开（公告）日：1987-11-03

  Substituted 2,3,3a,6-tetrahydro-6-oxobenzofuran derivatives have been prepared. These neolignans are found to have potent and specific PAF (Platelet-Activating-Factor) antagonistic activities and thereby useful in the treatment of various diseases or disorders mediated by PAF, for example, pain, fever, inflammation, cardiovascular disorder, asthma, lung edema, allergic disorders, skin diseases, psoriasis, toxic shock syndrome and adult respiratory distress syndrome.

  已制备取代的2,3,3a,6-四氢-6-氧基苯并呋喃衍生物。发现这些新木脂素具有强效且特异的PAF（血小板活化因子）拮抗活性，因此在治疗由PAF介导的各种疾病或紊乱中具有用处，例如疼痛、发热、炎症、心血管紊乱、哮喘、肺水肿、过敏性疾病、皮肤病、牛皮癣、中毒性休克综合征和成人呼吸窘迫综合征。