2-丙烯酸,3-(3,4-二氢-2,2-二甲基-2H-1-苯并吡喃-6-基)-,(2E)- | 12772-83-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 2-丙烯酸,3-(3,4-二氢-2,2-二甲基-2H-1-苯并吡喃-6-基)-,(2E)-
• 英文名称: dupracine
• 英文别名: (E)-3-(2,2-dimethylchroman-6-yl)-2-propenoic acid；3-[(2H)-2,2-dimethyl-3,4-dihydrobenzopyran-6-yl]-2E-propenoic acid；3-[2,2-dimethyl-3,4-dihydro-(2H)-benzopyran-6-yl]-2E-propenoic acid；(E)-3-(2,2-dimethylchroman-6-yl)acrylic acid；(E)-3-(2,2-dimethyl-3,4-dihydrochromen-6-yl)prop-2-enoic acid
• CAS: 12772-83-7
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: CRUHYIAGEXBWKH-GQCTYLIASA-N

物化性质

• 沸点：
  390.5±21.0 °C(Predicted)
• 密度：
  1.153±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-丙烯酸,3-(3,4-二氢-2,2-二甲基-2H-1-苯并吡喃-6-基)-,(2E)- 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Structure–activity relationship of piperine and its synthetic analogues for their inhibitory potentials of rat hepatic microsomal constitutive and inducible cytochrome P450 activities

  摘要：

  Inhibitors of drug metabolism have important implications in pharmaco-toxicology and agriculture. We have reported earlier that piperine, a major alkaloid of black and long peppers inhibits both constitutive and inducible cytochrome P450 (CYP)dependent drug metabolising enzymes. In the present study, an attempt has been made to prepare several novel synthetic analogues so as to relate various modifications in the parent molecule to the inhibition of CYP activities. Two types of mono-oxygenase reactions arylhydrocarbon hydroxylase (AHH) and 7-methoxycoumarin-O-demethylase (MOCD) have been studied. Inhibition studies were investigated in rat microsomal fraction prepared from untreated, 3MC- and PB- treated rat liver in vitro. Modifications were introduced into the piperine molecule: (i) in the phenyl nucleus, (ii) in the side chain and (iii) in the basic moiety. Thus, 38 compounds have been subjected to such studies, and simultaneously an attempt has also been made to arrive at the structure-activity relationship of synthetic analogues. In general, most of the inhibitory potential of the parent molecule is lost with modification in either of the three components of piperine. Saturation of the side chain resulted in significantly enhanced inhibition of CYP while modifications in the phenyl and basic moieties in few analogues offered maximal selectivity in inhibiting either constitutive or inducible CYP activities. Thus Few novel analogues as CYP inactivators have been synthesized which may have important consequences in pharmacokinetics and bioavailability of drugs. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00273-4
• 作为产物：
  描述：

  2-(3-hydroxy-3-methylbutyl)phenol 在 哌啶 、 吡啶 、 硫酸 、 三氯氧磷 作用下， 反应 25.25h， 生成 2-丙烯酸,3-(3,4-二氢-2,2-二甲基-2H-1-苯并吡喃-6-基)-,(2E)-
  参考文献：
  名称：

  设计，合成和测试潜在的抗渗胶剂。10.（2，2-二甲基苯并吡喃-6-基）链烷酸。

  摘要：

  合成了五种（2,2-二甲基苯并吡喃-6-基）链烷酸，并测试了其抗胶凝活性。可以预见，这些试剂可以通过疏水键结合到血红蛋白S的“供体-受体”区域的非极性位点上。一些（2，2-二甲基苯并吡喃-6-基）链烷酸在侧链上具有1-4个碳原子。链残基被设计成在受体位点相互作用，被合成，并且被发现是中等有效的抗胶凝剂。根据弱结合亲和力或对活性和非活性位点的多重结合，可以合理地观察到两种酸在低浓度下的弱活性。这些化合物对改变变构平衡的影响很小或可忽略不计。（2，

  DOI：

  10.1021/jm00394a007

文献信息

• Synthesis and anti-inflammatory activity evaluation of novel chroman derivatives
  作者：Akanksha Matta、Ajendra K. Sharma、Shilpi Tomar、Pei Cao、Sandeep Kumar、Sakshi Balwani、Balaram Ghosh、Ashok K. Prasad、Erik V. Van der Eycken、Anthony L. DePass、Jesper Wengel、Virinder S. Parmar、Christophe Len、Brajendra K. Singh

  DOI：10.1039/d0nj02125c

  日期：——

  In an effort to develop potent anti-inflammatory agents, a series of novel chroman derivatives including acyclic amidochromans, chromanyl esters and chromanyl acrylates have been designed, synthesized and fully characterized. These chroman analogues were screened for their anti-inflammatory activities through inhibition of the TNF-α-induced ICAM-1 expression on human endothelial cells. A structure–activity

  为了开发有效的抗炎剂，已经设计，合成并充分表征了一系列新的苯并二氢吡喃衍生物，包括无环酰胺基苯并二氢吡喃，苯并二氢吡喃酯和苯并二氢吡喃苯甲酸酯。通过抑制人内皮细胞上TNF-α诱导的ICAM-1表达，筛选了这些苯并吡喃类似物的抗炎活性。还建立了结构与活性的关系，并且发现对于羧基苯并二氢吡喃和酰胺基苯并二氢吡喃，酰胺部分的链长，侧链的支化以及苯环上取代基的存在对它们的抑制活性，而在丙烯酸苯丙酯中，甲氧基的数量，它们在苯环上的相对位置以及α中官能团的存在，β-不饱和酯部分对它们的活性起关键作用。复合发现14（N-己基-7-羟基-2,2-二甲基苯并吡喃-6-羧酰胺）是抑制内皮细胞上TNF-α诱导的ICAM-1表达的最有效化合物。
• Design, synthesis, and biological evaluation of novel diarylalkyl amides as TRPV1 antagonists
  作者：Fu-Nan Li、Nam-Jung Kim、Seung-Mann Paek、Do-Yeon Kwon、Kyung Hoon Min、Yeon-Su Jeong、Sun-Young Kim、Young-Ho Park、Hee-Doo Kim、Hyeung-Geun Park、Young-Ger Suh

  DOI：10.1016/j.bmc.2009.04.010

  日期：2009.5

  We have developed a new class of diarylalkyl amides as novel TRPV1 antagonists. They exhibited potent Ca-45(2+) uptake inhibitions in rat DRG neuron. In particular, the amide 59 was identified as a potent antagonist with IC50 of 57 nM. The synthesis and structure-activity relationship of the diarylalkyl amides are also described. (C) 2009 Elsevier Ltd. All rights reserved.
• Structure–activity relationship of piperine and its synthetic analogues for their inhibitory potentials of rat hepatic microsomal constitutive and inducible cytochrome P450 activities
  作者：Surrinder Koul、Jawahir L. Koul、Subhash C. Taneja、Kanaya L. Dhar、Deshvir S. Jamwal、Kuldeep Singh、Rashmeet K. Reen、Jaswant Singh

  DOI：10.1016/s0968-0896(99)00273-4

  日期：2000.1

  Inhibitors of drug metabolism have important implications in pharmaco-toxicology and agriculture. We have reported earlier that piperine, a major alkaloid of black and long peppers inhibits both constitutive and inducible cytochrome P450 (CYP)dependent drug metabolising enzymes. In the present study, an attempt has been made to prepare several novel synthetic analogues so as to relate various modifications in the parent molecule to the inhibition of CYP activities. Two types of mono-oxygenase reactions arylhydrocarbon hydroxylase (AHH) and 7-methoxycoumarin-O-demethylase (MOCD) have been studied. Inhibition studies were investigated in rat microsomal fraction prepared from untreated, 3MC- and PB- treated rat liver in vitro. Modifications were introduced into the piperine molecule: (i) in the phenyl nucleus, (ii) in the side chain and (iii) in the basic moiety. Thus, 38 compounds have been subjected to such studies, and simultaneously an attempt has also been made to arrive at the structure-activity relationship of synthetic analogues. In general, most of the inhibitory potential of the parent molecule is lost with modification in either of the three components of piperine. Saturation of the side chain resulted in significantly enhanced inhibition of CYP while modifications in the phenyl and basic moieties in few analogues offered maximal selectivity in inhibiting either constitutive or inducible CYP activities. Thus Few novel analogues as CYP inactivators have been synthesized which may have important consequences in pharmacokinetics and bioavailability of drugs. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Design, synthesis, and testing of potential antisickling agents. 10. 2,2-Dimethylchroman-6-ylalkanoic acids
  作者：Majekodunmi O. Fatope、Donald J. Abraham

  DOI：10.1021/jm00394a007

  日期：1987.11

  Five (2,2-dimethylchroman-6-yl)alkanoic acids were synthesized and tested for antigelling activities. It was envisioned that these agents might bind via hydrophobic bonding to nonpolar sites of the "donor-acceptor" regions of hemoglobin S. Several (2,2-dimethylchroman-6-yl)alkanoic acids containing 1-4 carbon atoms on the side-chain residue were designed to interact at the acceptor site, were synthesized

  合成了五种（2,2-二甲基苯并吡喃-6-基）链烷酸，并测试了其抗胶凝活性。可以预见，这些试剂可以通过疏水键结合到血红蛋白S的“供体-受体”区域的非极性位点上。一些（2，2-二甲基苯并吡喃-6-基）链烷酸在侧链上具有1-4个碳原子。链残基被设计成在受体位点相互作用，被合成，并且被发现是中等有效的抗胶凝剂。根据弱结合亲和力或对活性和非活性位点的多重结合，可以合理地观察到两种酸在低浓度下的弱活性。这些化合物对改变变构平衡的影响很小或可忽略不计。（2，