(E)-1-(2-hydroxyphenyl)-3-(4-methylsulfanylphenyl)prop-2-en-1-one | 936372-02-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-1-(2-hydroxyphenyl)-3-(4-methylsulfanylphenyl)prop-2-en-1-one
• CAS: 936372-02-0
• 化学式: C₁₆H₁₄O₂S
• 分子量: 270.352
• InChiKey: ILBUFDBWHFQAKZ-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-1-(2-hydroxyphenyl)-3-(4-methylsulfanylphenyl)prop-2-en-1-one 在 碘 作用下， 以 二甲基亚砜 为溶剂， 生成 (4-(methylthio)phenyl)-4H-1-benzopyran-4-one
  参考文献：
  名称：

  2,3-Diarylbenzopyran derivatives as a novel class of selective cyclooxygenase-2 inhibitors

  摘要：

  A new series of cyclooxygenase-2(COX-2) inhibitors with naturally occurring flavone as the main skeleton has been synthesized and their biological activities were evaluated for cyclooxygenase inhibitory activity. Rational structural modifications were applied to potent COX-2 inhibitors to obtain the desired pharmacokinetic profiles for improved oral anti-inflammatory activity. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00952-6
• 作为产物：
  描述：

  2'-羟基苯乙酮 、 4-(甲基巯基)苯甲醛 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 (E)-1-(2-hydroxyphenyl)-3-(4-methylsulfanylphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis, antimycobacterial activity evaluation, and QSAR studies of chalcone derivatives

  摘要：

  In order to develop relatively small molecules as antimycobacterial agents, twenty-five chalcones were synthesized, their activity was evaluated, and quantitative structure-activity relationship (QSAR) was developed. The synthesis was based on the Claisen-Schimdt scheme and the resultant compounds were tested for antitubercular activity by luciferase reporter phage (LRP) assay. Compound C-24 was found to be the most active (similar to 99%) in this series based on the percentage reduction in Relative Light Units at both 50 and 100 mu g/ml levels, followed by compound C-21. Four compounds at the 50 mu g/ml and eight compounds at the 100 mu g/ml showed activity above 90% level. QSAR model was developed between activity and spatial, topological, and ADME descriptors for the 50 mu g/ml data. The statistical measures such as r, r(2), q(2), and F values obtained for the training set were in acceptable range and hence this relationship was used for the test set. The predictive ability of the model is satisfactory (q(2) = 0.56) and it can be used for designing similar group of compounds. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.112

文献信息

• [EN] DIARYLBENZOPYRAN DERIVATIVES AS CYCLOOXYGENASE-2 INHIBITORS<br/>[FR] DERIVES DE DIARYLBENZOPYRANE UTILISES COMME INHIBITEURS DE CYCLOOXYGENASE-2
  申请人：PACIFIC CORP

  公开号：WO2000010993A1

  公开（公告）日：2000-03-02

  The diarylbenzopyran derivatives represented by general formula (I): wherein Y is an oxygen atom or a sulfur atom; R?1 and R2¿, identical to or different from each other, are independently a hydrogen atom, a halogen atom, a C¿1?-C6 lower alkyl group, a trifluromethyl group, an alkoxy group, a hydroxy group, a nitro group, a nitrile group, or a carboxyl group; R?3¿ is a group of a formula: S(O)nR5 wherein n is an integer of 0∩2, R5 is a hydrogen atom, a C¿1?-C6 lower alkyl group, or a group of a formula: NR?6R7¿ wherein R?6 and R7¿, identical to or different from each other, are independently a hydrogen atom, or a C¿1?-C6 lower alkyl group; R?4¿ is oxazolyl, benzo[b]thienyl, furanyl, thienyl, naphthyl, thiazolyl, indolyl, pyrolyl, benzofuranyl, benzodioxoyl, or a substituted group presented by structures (a), (b), (c) or (d) wherein R8 through R12 identical to or different from one another, are independently a hydrogen atom, a halogen atom, a C¿1?-C6 lower alkyl group, a trifluromethyl group, an alkoxy group, a hydroxy group, a hydroxyalkyl group, a nitro group, a group of a formula: S(O)nR?5¿, a group of a formula NR6R7, a trifluromethoxy group, a nitrile group, a carboxyl group, an acetyl group, or a formyl group wherein n, R?5, R6 and R7¿ have the same meaning as defined X and R3 above; and R13 is a hydrogen atom, a halogen atom, a C¿1?-C6 lower alkyl group, a trifluromethyl group, an alkoxy group, a hydroxy group, a trifluromethoxy group, a carboxyl group, or an acetyl group; or their pharmaceutically acceptable salts are disclosed. And also cyclooxygenase-2 inhibitor composition, which consists of an effective amount of a diarylbenzopyran derivative and pharmaceutically acceptable salts of diarylbenzopyran derivative and shows an excellent selective inhibition, is disclosed.

  通式（I）所代表的二芳基苯并吡喃衍生物：其中Y是氧原子或硫原子；R1和R2，相同或不同，分别独立地是氢原子、卤素原子、C1-C6低烷基、三氟甲基基团、烷氧基、羟基、硝基、腈基或羧基；R3是公式S（O）nR5的基团，其中n是0-2的整数，R5是氢原子、C1-C6低烷基或公式NR6R7的基团，其中R6和R7，相同或不同，独立地是氢原子或C1-C6低烷基；R4是噁唑基、苯并[b]噻吩基、呋喃基、噻吩基、萘基、噻唑基、吲哚基、吡咯基、苯并呋喃基、苯并二氧杂环基或由结构（a）、（b）、（c）或（d）所示的取代基团，其中R8至R12相同或不同，独立地是氢原子、卤素原子、C1-C6低烷基、三氟甲基基团、烷氧基、羟基、羟基烷基基团、硝基、公式S（O）nR5的基团、公式NR6R7的基团、三氟甲氧基团、腈基、羧基、乙酰基或甲酰基，其中n、R5、R6和R7的含义与上述X和R3的定义相同；R13是氢原子、卤素原子、C1-C6低烷基、三氟甲基基团、烷氧基、羟基、三氟甲氧基团、羧基或乙酰基；或其药学上可接受的盐。还披露了环氧合酶-2抑制剂组合物，其由一种二芳基苯并吡喃衍生物的有效量和药学上可接受的二芳基苯并吡喃衍生物盐组成，并显示出优异的选择性抑制作用。
• Synthesis, antimycobacterial activity evaluation, and QSAR studies of chalcone derivatives
  作者：P.M. Sivakumar、S. Prabu Seenivasan、Vanaja Kumar、Mukesh Doble

  DOI：10.1016/j.bmcl.2006.12.112

  日期：2007.3

  In order to develop relatively small molecules as antimycobacterial agents, twenty-five chalcones were synthesized, their activity was evaluated, and quantitative structure-activity relationship (QSAR) was developed. The synthesis was based on the Claisen-Schimdt scheme and the resultant compounds were tested for antitubercular activity by luciferase reporter phage (LRP) assay. Compound C-24 was found to be the most active (similar to 99%) in this series based on the percentage reduction in Relative Light Units at both 50 and 100 mu g/ml levels, followed by compound C-21. Four compounds at the 50 mu g/ml and eight compounds at the 100 mu g/ml showed activity above 90% level. QSAR model was developed between activity and spatial, topological, and ADME descriptors for the 50 mu g/ml data. The statistical measures such as r, r(2), q(2), and F values obtained for the training set were in acceptable range and hence this relationship was used for the test set. The predictive ability of the model is satisfactory (q(2) = 0.56) and it can be used for designing similar group of compounds. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthetic chalcones, flavanones, and flavones as antitumoral agents: Biological evaluation and structure–activity relationships
  作者：Mauricio Cabrera、Macarena Simoens、Gabriela Falchi、M. Laura Lavaggi、Oscar E. Piro、Eduardo E. Castellano、Anabel Vidal、Amaia Azqueta、Antonio Monge、Adela López de Ceráin、Gabriel Sagrera、Gustavo Seoane、Hugo Cerecetto、Mercedes González

  DOI：10.1016/j.bmc.2007.03.031

  日期：2007.5

  A series of synthetic chalcones, flavanones, and flavones has been synthesized and evaluated for antitumor activity against the human kidney carcinoma cells TK-10, human mammary adenocarcinoma cells MCF-7 (estrogen receptor-positive), and human colon adenocarcinoma cells HT-29. The most active series is the chalcone ones with the best results against TK-10 and HT-29 cells. Fourteen out of 53 analyzed compounds resulted very active against at least two of the studied tumoral cells. Alkaline single cell gel electrophoresis, comet assay, was performed as a study of the chromosomal aberrations promoted by the compounds on normal cells. Four active and two inactive chalcones were studied in the comet assay against normal human kidney cells (HK-2). A structure-activity relationship analysis of these compounds was performed and for 4- and 3,4-disubstituted derivatives a quantitative correlation was obtained in the case of anti-HT-29 activity. (c) 2007 Published by Elsevier Ltd.
• DIARYLBENZOPYRAN DERIVATIVES AS CYCLOOXYGENASE-2 INHIBITORS
  申请人：PACIFIC CORPORATION

  公开号：EP1105384A1

  公开（公告）日：2001-06-13
• US6340694B1
  申请人：——

  公开号：US6340694B1

  公开（公告）日：2002-01-22