1-[(2H)-2,2-dimethyl-3,4-dihydrobenzopyran-6-yl]ethanol | 261913-27-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 1-[(2H)-2,2-dimethyl-3,4-dihydrobenzopyran-6-yl]ethanol
• 英文别名: 1-(2,2-dimethylchroman-6-yl)ethanol；1-(2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-6-yl)ethan-1-ol；1-(2,2-dimethyl-3,4-dihydrochromen-6-yl)ethanol
• CAS: 261913-27-3
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: RUTIRHGKMLWGQH-UHFFFAOYSA-N

物化性质

• 沸点：
  315.4±21.0 °C(Predicted)
• 密度：
  1.048±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[(2H)-2,2-dimethyl-3,4-dihydrobenzopyran-6-yl]ethanol 在 氢氧化钾 、 sodium hydride 、 三氯氧磷 作用下， 以 甲醇 、 乙二醇二甲醚 为溶剂， 反应 9.0h， 生成 5-[(2H)-2,2-dimethyl-3,4-dihydrobenzopyran-6-yl]-2E,4E-pentadienoic acid
  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：

  2,2-二甲基-6-乙酰基苯并二氢吡喃 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以100 %的产率得到1-[(2H)-2,2-dimethyl-3,4-dihydrobenzopyran-6-yl]ethanol
  参考文献：
  名称：

  Uniflorol类似物的合成及其抗利什曼原虫活性

  摘要：

  色满酮是苯并吡喃家族的一个子集，作为天然产物和合成衍生物表现出多种生物活性。其中，我们选择天然产物uniflorol（一种具有α,β-不饱和酮侧链的4-苯并二氢吡喃酮）作为先导化合物，因为它具有已报道的抗利什曼原虫特性。我们设计并合成了四个系列的新型化合物，改变了苯并吡喃核心周围的取代模式，并评估了这些化合物对婴儿利什曼原虫无鞭毛体的抗利什曼原虫活性。我们制备并表征了 24 种新型化合物；经过筛选，12 种化合物的活性值<50 μM，其中最有效的化合物 16d，其 IC 50 为 7.29 μM。带有苯基烯基基序（例如肉桂基、苯乙烯基或更具亲脂性的延伸）的化合物的活性受到青睐，而酰胺类似物保留了活性。 Uniflorol 类似物作为新型结构有望开发潜在的抗利什曼原虫药物。

  DOI：

  10.1007/s00044-024-03275-3

文献信息

• Dihydropyrimidinones: efficient one-pot green synthesis using Montmorillonite-KSF and evaluation of their cytotoxic activity
  作者：Saleem Farooq、Fahad A. Alharthi、Ali Alsalme、Aashiq Hussain、Bashir A. Dar、Abid Hamid、S. Koul

  DOI：10.1039/d0ra09072g

  日期：——

  A simple, efficient, cost-effective, recyclable and green approach has been developed for the synthesis of new dihydropyrimidinone analogs via the Biginelli reaction. The methodology involves a multicomponent reaction catalyzed by “HPA-Montmorillonite-KSF” as a reusable and heterogeneous catalyst. This method gives an efficient and much improved modification of the original Biginelli reaction, in terms

  已经开发了一种简单、高效、经济、可回收和绿色的方法，用于通过Biginelli 反应合成新的二氢嘧啶酮类似物。该方法涉及由“HPA-蒙脱石-KSF”作为可重复使用的非均相催化剂催化的多组分反应。该方法在无溶剂条件下的产率和反应时间短方面对原始 Biginelli 反应进行了有效且大大改进的改进。所有衍生物都针对一组四种不同的人类癌细胞系进行细胞毒性筛选，即. 结肠 (Colo-205)、前列腺 (PC-3)、白血病 (THP-1) 和肺 (A549) 以检查它们对百分比增长的影响。MTT [3-(4,5-二甲基噻唑-基)-二苯基溴化四唑]细胞毒性试验用于检查IC 50值。在合成的类似物中，16a对肺 (A549)、白血病 (THP-1)、前列腺 (PC-3)和结肠（Colo-205）癌症系，分别。16a _通过克隆形成（集落形成）和划痕运动（伤口愈合）测定进一步检查了类似物对癌细胞特性的影响，从而发现它减少了肺癌细胞系
• 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.
• 10.1007/s00044-024-03275-3
  作者：da Silva Cardoso, Paula、Niero, Luana Budny、Frizon, Tiago Elias Allievi、DalBó, Silvia、Le Lamer, Anne Cécile、Gouault, Nicolas、de Aguiar Amaral, Patrícia、Barlow, James W.

  DOI：10.1007/s00044-024-03275-3

  日期：——

  β-unsaturated ketone side chain, as a lead compound due to its reported anti-leishmanial properties. We designed and synthesised four series of novel compounds, varying the substitution patterns around the benzopyran core, and evaluated the compounds for anti-leishmanial activity against amastigotes of L. infantum. We prepared and characterised 24 novel compounds; upon screening, 12 compounds demonstrated

  色满酮是苯并吡喃家族的一个子集，作为天然产物和合成衍生物表现出多种生物活性。其中，我们选择天然产物uniflorol（一种具有α,β-不饱和酮侧链的4-苯并二氢吡喃酮）作为先导化合物，因为它具有已报道的抗利什曼原虫特性。我们设计并合成了四个系列的新型化合物，改变了苯并吡喃核心周围的取代模式，并评估了这些化合物对婴儿利什曼原虫无鞭毛体的抗利什曼原虫活性。我们制备并表征了 24 种新型化合物；经过筛选，12 种化合物的活性值<50 μM，其中最有效的化合物 16d，其 IC 50 为 7.29 μM。带有苯基烯基基序（例如肉桂基、苯乙烯基或更具亲脂性的延伸）的化合物的活性受到青睐，而酰胺类似物保留了活性。 Uniflorol 类似物作为新型结构有望开发潜在的抗利什曼原虫药物。