trans-3,3'-Dihydroxy-α,β-dimethylstilben | 74944-95-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: trans-3,3'-Dihydroxy-α,β-dimethylstilben
• 英文别名: (E)-3,3′-[1,2-dimethyl-1,2-ethenediyl]bisphenol；(E)-3,3'-[1,2-dimethyl-1,2-ethenediyl]bisphenol；trans-3,3'-Dihydroxy-alpha,beta-dimethylstilben；3-[(E)-3-(3-hydroxyphenyl)but-2-en-2-yl]phenol
• CAS: 74944-95-9
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: LZVBSFWOSQFAFL-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-3,3'-Dihydroxy-α,β-dimethylstilben 在 吡啶 、 间氯过氧苯甲酸 作用下， 以 乙醚 为溶剂， 反应 0.5h， 生成 [3-[3-(3-Acetyloxyphenyl)-2,3-dimethyloxiran-2-yl]phenyl] acetate
  参考文献：
  名称：

  Mammary tumor inhibiting effect of 3,3'-diacetoxy-.alpha.,.beta.-dialkylstilbenes and of related stilbene oxides

  摘要：

  3,3'-Diacetoxy-alpha, beta-dialkylstilbenes (alkyl = CH3 to C4H9, 1-4) 3,3'-dihydroxy-alpha, beta-diethylstilbene (5), and their corresponding stilbene oxides (6-10) were synthesized. Compounds 1-10 competitively antagonized in vitro the interaction of [3H]estradiol with its receptor. 3,3'-Diacetoxy-alpha, beta-diethylstilbene (2), 3,3'-diacetoxy-alpha, beta-diethylstilbene oxide (7), and their phenolic analogues (5 and 10) were most effective. Shortening or lengthening the alkyl side chains led to a decrease in receptor affinity. Among the stilbenes and epoxides, those with C2H5 and C3H7 groups (2, 3, 5 and 7, 8, 10) caused the strongest inhibition of the growth of a hormone-dependent postmenopausal human mammary carcinoma serially implanted in nude mice. The strong antitumor activity of 5 and 10 was confirmed by experiments on the 9,10-dimethyl-1,2-benzanthracene-induced, hormone-dependent mammary carcinoma of the Sprague-Dawley rat.

  DOI：

  10.1021/jm00344a010
• 作为产物：
  描述：

  3-甲氧基苯乙酮 在 二氧化硫 、 三溴化硼 、 一水合肼 、 mercury(II) oxide 、 barium(II) oxide 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 、 Petroleum ether 为溶剂， 反应 36.0h， 生成 trans-3,3'-Dihydroxy-α,β-dimethylstilben
  参考文献：
  名称：

  3,3'-二羟基-α, β-二烷基二苯乙烯型的乳腺肿瘤抑制抗雌激素

  摘要：

  反式-3,3'-二羟基-α, β-二烷基二苯乙烯 1,3-5，抗雌激素对 DMBA 诱导的 SD 大鼠（尤其是 3 和 4）的激素依赖性乳腺癌有显着影响，是由3-甲氧基苯基重氮烷 c 与 SO2 转化形成 1,1-二氧代-2,5-二烷基-2,5-二-(3'-甲氧基苯基)-Δ3-1,3,4-噻二唑啉 d, 热分解d 到 3,3'-二甲氧基-α, β-二烷基二苯乙烯 e 和 e 的醚裂解可用。

  DOI：

  10.1002/ardp.19803131105

文献信息

• Compositions and methods for adipocyte modulation
  申请人：Patel Niketa A.

  公开号：US09458086B1

  公开（公告）日：2016-10-04

  Modified stilbenoids and formulations thereof are provided. The modified stilbenoids can include one or more amino or amino-alkyl substituents. The formulation can be for the treatment or prevention of obesity and the modified stilbenoid present in an effective amount to alleviate or prevent the onset of one or more symptoms of obesity. Methods of making the modified stilbenoids and formulations thereof are provided. Methods are provided for treating a subject with a modified stilbenoid in an effective amount to alleviate or prevent one or more symptoms associated with diabetes, cardiovascular disease, high blood pressure, deep vein thrombosis, osteoarthritis, obstructive sleep apnea, cancer, and non-alcoholic fatty liver disease. The administration of the modified stilbenoids can result in decreased levels of PKCδII, PKCδVIII, substantially unaltered expression of PKCδI; a decreased number of adipocytes; increased weight and/or fat loss; or a combination thereof.

  提供了改性的苯乙烯类化合物及其制剂。改性苯乙烯类化合物可以包括一个或多个氨基或氨基烷基取代基。该制剂可用于治疗或预防肥胖症，并且改性苯乙烯类化合物以有效量存在，以缓解或预防肥胖症的一个或多个症状。提供了制备改性苯乙烯类化合物及其制剂的方法。提供了使用有效量的改性苯乙烯类化合物治疗受试者，以缓解或预防与糖尿病、心血管疾病、高血压、深静脉血栓、骨关节炎、阻塞性睡眠呼吸暂停、癌症和非酒精性脂肪肝病等相关的一个或多个症状的方法。改性苯乙烯类化合物的给药可以导致PKCδII、PKCδVIII的水平降低，PKCδI的表达基本不变；脂肪细胞数量减少；体重和/或脂肪减少增加；或其组合。
• Identification of novel SAR properties of the Jak2 small molecule inhibitor G6: Significance of the para-hydroxyl orientation
  作者：Rebekah Baskin、Meghanath Gali、Sung O. Park、Zhizhuang Joe Zhao、György M. Keserű、Kirpal S. Bisht、Peter P. Sayeski

  DOI：10.1016/j.bmcl.2011.12.042

  日期：2012.2

  In this study, we analyzed the structure-activity relationship properties of the small molecule Jak2 inhibitor G6. We synthesized a set of derivatives containing the native para-hydroxyl structure or an alternative meta-hydroxyl structure and examined their Jak2 inhibitory properties. We found that the para-hydroxyl derivative known as NB15 had excellent Jak2 inhibitory properties in silico, in vitro, and ex vivo when compared with meta-hydroxyl derivatives. These results indicate that NB15 is a potent derivative of the Jak2 inhibitor G6, and that maintaining the para-hydroxyl orientation of G6 is critical for its Jak2 inhibitory potential. (C) 2011 Elsevier Ltd. All rights reserved.
• SCHNEIDER M.; ANGERER E. VON; KRANZFELDER G.; SCHOENENBERGER H., ARCH. PHARM., 1980, 313, NO 11, 919-925
  作者：SCHNEIDER M.、 ANGERER E. VON、 KRANZFELDER G.、 SCHOENENBERGER H.

  DOI：——

  日期：——
• KINASE INHIBITOR COMPOUNDS
  申请人：University of Florida Research Foundation, Inc.

  公开号：EP2376425A2

  公开（公告）日：2011-10-19
• VIMENTIN AS A BIOMARKER FOR THE PROGRESSION OF MYELOPROLIFERATIVE NEOPLASMS
  申请人：University of Florida Research Foundation

  公开号：US20140248634A1

  公开（公告）日：2014-09-04

  The disclosure relates to novel compounds that are capable of modulating Jak2 kinase activities, compounds that have therapeutic use in treating or preventing a subject suffering from or susceptible to a Jak2 mediated disease or disorder, and methods of use and compositions thereof.