(5As,7s)-7-异丙烯基-3-甲基-6,7,8,9-四氢-5ah-吡喃并[4,3-b]色烯-1-酮 | 194937-75-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 中文名称: (5As,7s)-7-异丙烯基-3-甲基-6,7,8,9-四氢-5ah-吡喃并[4,3-b]色烯-1-酮
• 英文名称: (5aS,7S)-7-isopropenyl-3-methyl-1H,7H-5a,6,8,9-tetrahydro-1-oxopyrano[4,3-b][1]benzopyran
• 英文别名: (5aS,7S)-7-Isopropenyl-3-methyl-6,7,8,9-tetrahydro-5aH-pyrano[4,3-b]chromen-1-one；(5aS,7S)-3-methyl-7-prop-1-en-2-yl-6,7,8,9-tetrahydro-5aH-pyrano[4,3-b]chromen-1-one
• CAS: 194937-75-2
• 化学式: C₁₆H₁₈O₃
• 分子量: 258.317
• InChiKey: GRYISIULMJKOLF-FZMZJTMJSA-N

物化性质

• 熔点：
  140-141 °C
• 沸点：
  429.2±45.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5As,7s)-7-异丙烯基-3-甲基-6,7,8,9-四氢-5ah-吡喃并[4,3-b]色烯-1-酮 在 硼烷四氢呋喃络合物 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 (5aS,7S)-3-methyl-7-(2-methanesulfonyloxy-1-methylethyl)-1H,7H-5a,6,8,9-tetrahydro-1-oxopyrano[4,3-b][1]benzopyran
  参考文献：
  名称：

  三环吡喃酮的合成及生物活性

  摘要：

  在搜索条件的改善淀粉样蛋白β（Aβ）肽，三环吡喃酮的新衍生物的毒性的化合物的（1 - 7）的合成和它们的生物活性评价。羧酸酯和酰胺衍生物1 - 4从（5a的C3甲基的选择性合成羧化小号，7小号） - {7-异丙烯基-3-甲基-1- ħ，7 ħ -5a，6,8,9-四氢-1-氧杂吡喃并[4,3- b ] [1]苯并吡喃（8）与LDA，然后用氯甲酸苄酯或二氧化碳提供酯1和羧酸9， 分别。三种同分异构的三环吡喃酮，5 - 7，含有C7侧链腺嘌呤部分从甲磺酸酯的烷基化合成13与腺嘌呤，和氯嘌呤的位移15与胺14。虽然C3苄氧羰基类似物1 - 3有边际ACAT和CETP活性，它们的改性天冬氨酸模4和C3-甲基-C 7 - （Ñ 3-腺嘌呤基）-2-丙基类似物6示出在防止神经元细胞死亡的效果显著从淀粉样β前体蛋白（APP）的Aβ或含Aβ的C末端片段（CTF）的细胞内蓄积的毒性中获悉。在保护Aβ诱导的神经元细胞死亡方面，N

  DOI：

  10.1016/s0040-4020(03)00687-2
• 作为产物：
  描述：

  4-羟基-6-甲基-2-吡喃酮 、 (S)-(-)-紫苏醛 在 L-脯氨酸 作用下， 以78%的产率得到(5As,7s)-7-异丙烯基-3-甲基-6,7,8,9-四氢-5ah-吡喃并[4,3-b]色烯-1-酮
  参考文献：
  名称：

  [EN] TRICYCLIC PYRONE COMPOUNDS REDUCE AMYLOID BETA AGGREGATES
  [FR] COMPOSÉS DE PYRONE TRICYCLIQUE RÉDUISANT LES AGRÉGATS DE PROTÉINES BÊTA-AMYLOÏDES

  摘要：

  本文介绍了具有高口服生物利用度、优良的血脑屏障通透性和低毒性的三环吡喃化合物。将这些化合物用于阿尔茨海默病转基因模型，可以显著减少脑部可溶性和不可溶性Αβ物种的产生，而不影响一般行为和运动协调。此外，这些化合物不仅可以阻止神经元内和细胞外Αβ聚集物的毒性和形成，还可以增加细胞胆固醇外流，恢复轴突运输，并增强海马突触可塑性。

  公开号：

  WO2015048821A1

文献信息

• Methods of treating cataracts and diabetic retinopathy with tricyclic pyrones
  申请人：Hua Duy H.

  公开号：US06916824B1

  公开（公告）日：2005-07-12

  Water-soluble, cell permeable aldose reductase inhibitors are presented. These compounds prevent the effects of galactosemia in patients. The compounds prevent both the accumulation of polyols and the change in levels of protein kinase C gamma observed during diabetes and galactosemia.

  提供了水溶性、细胞渗透性的醛糖还原酶抑制剂。这些化合物可以预防患者中的半乳糖尿病效应。这些化合物可以防止多元醇的积累，以及在糖尿病和半乳糖尿病期间观察到的蛋白激酶Cγ水平的变化。
• Syntheses of tricyclic pyrones and pyridinones and protection of Aβ-peptide induced MC65 neuronal cell death
  作者：Sandeep Rana、Hyun-Seok Hong、Lydia Barrigan、Lee-Way Jin、Duy H. Hua

  DOI：10.1016/j.bmcl.2008.12.060

  日期：2009.2

  The SβC gene is conditionally expressed a 99-residue carboxy terminal fragment, C99, of amyloid precursor protein in MC65 cells and causes cell death. Consequently, MC65 cell line was used to identify inhibitors of toxicity related to intracellular amyloid β (Aβ) oligomers. Compounds that reduce the level of Aβ peptides, prevent Aβ aggregation, or eliminate existing Aβ aggregates may be used in the

  SβC基因在MC65细胞中有条件表达淀粉样前体蛋白的99个残基羧基末端片段C99，并导致细胞死亡。因此，MC65细胞系用于鉴定与细胞内淀粉样蛋白β（Aβ）低聚物有关的毒性抑制剂。降低Aβ肽水平，防止Aβ聚集或消除现有Aβ聚集体的化合物可用于治疗阿尔茨海默氏病（AD）。以前，我们发现三环吡喃酮（TP）分子化合物1可防止MC65细胞死亡并抑制Aβ聚集。因此，合成了在C7侧链上含有杂环和在2或5位上具有氮的各种TP，并评估了它们对MC65细胞的保护活性。含有N3'-腺嘌呤部分的TP，例如化合物1和11个最活跃，其EC 50值分别为0.31和0.35μM。尽管缺少腺嘌呤部分，三环N5-类似物吡喃异喹啉酮13和N2-类似物吡喃吡啶酮20的EC 50值分别为2.49和1.25μM 。三环N2-和N5-类似物的进一步研究是必要的。
• A One-Pot Condensation of Pyrones and Enals. Synthesis of 1<i>H</i>,7<i>H</i>-5a,6,8,9-Tetrahydro-1-oxopyrano[4,3-<i>b</i>][1]benzopyrans
  作者：Duy H. Hua、Yi Chen、Hong-Sig Sin、Maria J. Maroto、Paul D. Robinson、Steven W. Newell、Elisabeth M. Perchellet、James B. Ladesich、Jonathan A. Freeman、Jean-Pierre Perchellet、Peter K. Chiang

  DOI：10.1021/jo970642d

  日期：1997.10.1

  Condensation of various 6-substituted 4-hydroxypyrones 1 with 1-cyclohexenecarboxaldehydes in the presence of L-proline in ethyl acetate gave high yields of substituted 1H,7H-5a,6,8,9-tetrahydro-1-oxopyrano[4,3-b][1]benzopyrans. The reaction presumably occurs via the 1,2-addition of the pyrone with the aldehyde followed by dehydration and then cyclization through a 6 Pi electrocyclic process. A remarkable asymmetric induction was obtained from a stereogenic center (C4) of the cyclohexenecarboxaldehyde [such as (S)-perillaldehyde] to provide only the C5a,7-trans tricyclic pyrone products. On the other hand, condensation of S-(formyloxy)- or 3-hydroxy-2-methyl-1-cyclohexene-carboxaldehydes with pyrones 1 gave mixtures of C5a,6-cis and -trans products. Several of the tricyclic pyrones strongly inhibit acetylcholinesterase activity, DNA synthesis, and tumor cell growth in vitro.
• Synthesis and anti-norovirus activity of pyranobenzopyrone compounds
  作者：Laxman Pokhrel、Yunjeong Kim、Thi D.T. Nguyen、Allan M. Prior、Jianyu Lu、Kyeong-Ok Chang、Duy H. Hua

  DOI：10.1016/j.bmcl.2012.03.084

  日期：2012.5

  During the last decade, noroviruses have gained media attention as the cause of large scale outbreaks of gastroenteritis on cruise ships, dormitories, nursing homes, etc. Although noroviruses do not multiply in food or water, they can cause large outbreaks because approximately 10-100 virions are sufficient to cause illness in a healthy adult. Recently, it was shown that the activity of acyl-coenzyme A:cholesterol acyltransferase-1 (ACAT1) enzyme may be important in norovirus infection. In search of anti-noroviral agents based on the inhibition of ACAT1, we synthesized and evaluated the inhibitory activities of a class of pyranobenzopyrone molecules containing amino, pyridine, substituted quinolines, or 7,8-benzoquinoline nucleus. Three of the sixteen evaluated compounds possess ED50 values in the low micrometer range. 2-Quinolylmethyl derivative 3A and 4-quinolylmethyl derivative 4A showed ED50 values of 3.4 and 2.4 mu M and TD50 values of >200 and 96.4 mu M, respectively. The identified active compounds are suitable for further modification for the development of anti-norovirus agents. (C) 2012 Elsevier Ltd. All rights reserved.
• (5a<i>S</i>,7<i>S</i>)-7-Isopropenyl-3-methyl-5a,6,8,9-tetrahydro-1<i>H</i>,7<i>H</i>-pyrano[4,3-<i>b</i>][1]benzopyran-1-one
  作者：D. H. Hua、Y. Chen、P. D. Robinson、C. Y. Meyers

  DOI：10.1107/s0108270197011220

  日期：1997.12.15

  A remarkable asymmetric induction was observed in the one-pot condensation reaction of (S)-(-)-perillaldehyde with 4-hydroxy-6-methyl-2-pyrone in the presence of L-proline which provided the title compound, C16H18O3, a tricyclic pyrone, as a single diastereomer in 78% yield. As the configuration of the cyclohexane C atom holding the isopropenyl group is the same as that in the (S)-aldehyde substrate, the total absolute stereochemistry could be elucidated from its X-ray structure. The cyclohexane ring has a chair conformation in which the juncture H atom (H5a) is axially oriented and the isopropenyl substituent is equatorial.