CAS: 31685-80-0; Pinusolide
该化合物是一种复杂的有机化合物,其特征是其复杂的分子结构,包括多个手性中心和功能组.该物质具有氯化萘核心特征,是一种多环芳烃,并经过进一步修改,配有碳瓶状酯组,有助于其再活性和有机合成中的潜在应用. 呋喃运动的存在表明潜在的生物活动,因为呋喃衍生物往往存在于天然产品和药品中.该化合物的立体化学中心以其特定配置为标志,表明其可能表现出生物系统的独特性与互动性. 其分子量,溶性以及稳定性将取决于研究的具体情况,使其成为对医药化学和材料科学进行进一步研究的候选对象.
- 英文名称Pinusolide
- 中文名称红松内酯
- IUPAC名称Pinusolide
- 其它别名Pinusolide; (1S,8Aα)-5β-[2-(2,5-Dihydro-2-Oxofuran-3-yl)Ethyl]Decahydro-1,4Aβ-Dimethyl-6-Methylene-1β-Naphthalenecarboxylic Acid Methyl Ester; Methyl (1S,4Ar,5S,8Ar)-1,4A-Dimethyl-6-Methylidene-5-[2-(5-Oxo-2H-Furan-4-yl)Ethyl]-3,4,5,7,8,8A-Hexahydro-2H-Naphthalene-1-Carboxylate; 1-Naphthalenecarboxylicacid,5-[2-(2,5-Dihydro-2-Oxo-3-Furanyl)Ethyl]Decahydro-1,4A-Dimethyl-6-Methylene-,Methyl Ester, (1S,4Ar,5S,8Ar)-
- CAS编号31685-80-0
- MFCD编号:MFCD20260814
- FDA UNII编号:6HV7MVZ4Y7
- 分子式:C21H30O4分子量:346.47
- 产品CID: 1306776
- 产品分类天然产物 → 萜类
物理性质
- 熔点82-84 °C(溶剂: ligroine (8032-32-4))
- 沸点465.3±38.0 °C(预测)
- 闪点228.5 °C
- 密度1.10±0.1 g/cm3(预测)
- PSA:52.6
- LogP:4.520 (est)
- 折射率1.524
- 蒸汽压7.76E-09 mmHg at 25 °C
- 溶解性Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
- 外观形态粉末
- 储存条件Dry, dark and at 0 -4 C for short term (days to weeks) or -20 C for long term(months to years).
- 产品应用该化合物是已知的小盘活性因子(PAF)受体约束性对敌者;它减少肿瘤细胞扩散,并特别诱发多孔病.
上下游产品
diazomethane methyl 5-[2-(2,5-dimethoxy-2,5-dihydrofuran-3-yl)ethyl]-1,4a-dimethyl-6-methylidene-decahydronaphthalene-1-carboxylate methanol lambertianic acid methyl esterlambertianic acid methyl ester合成工艺路线路线简述
📜Methyl 5-[2-(2,5-Dimethoxy-2,5-Dihydrofuran-3-yl)Ethyl]-1,4A-Dimethyl-6-Methylidene-Decahydronaphthalene-1-Carboxylate置于盐酸体系中,用 1,4-二氧六环 作为反应溶剂,化学反应 0.5H,以67%的收率获得产物红松内酯
参考文献:Synthetic Transformations Of Higher Terpenoids: Xiv. Synthesis Of Pyrrololabdanoids From Lambertianic Acid
标题:Synthetic Transformations Of Higher Terpenoids: Xiv. Synthesis Of Pyrrololabdanoids From Lambertianic Acid
摘要:Treatment Of Lambertianic Acid Methyl Ester With Lead Tetraacetate Gave Terpenoid 2,5-Diacetoxydihydrofuran Which Reacted With Primary Amines To Yield 3-Terpenyl-Substituted Pyrrol-2(5H)-Ones; The Reaction With Bydrazine Led To The Corresponding Pyridazine Derivative. The Obtained Furanoterpenoids Underwent Oxidative Methoxylation By The Action Of N-Chlorobenzenesulfonamide Or N-Bromosuccinimide In Methanol. 2,5-Dimethoxydihydrofurans Thus Formed Were Smoothly Converted Into 3-Substituted Furan-2(5H)-One In Acid Medium. Hydrogenation Of 2,5-Dimethoxydihydrofurans,Followed By Treatment With Amines,Gave 1,3-Disubstituted Pyrroles.
DOI:10.1134/s1070428006060030
海关参考信息
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2901220000-丙烯
2905121000-正丙醇
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主要参考文献
1: Jin Y, Yang HO, Son JK, Chang HW. Pinusolide isolated from Biota orientalis inhibits 5-lipoxygenase dependent leukotriene C4 generation by blocking c-Jun N-terminal kinase pathway in mast cells. Biol Pharm Bull. 2012;35(8):1374-8. doi: 10.1248/bpb.b12-00271. 437(3):374-9. doi: 10.1016/j.bbrc.2013.06.084. Epub 2013 Jul 2. 65(1):39-42. doi: 10.1055/s-1999-13959. 150(1):65-71. doi: 10.1038/sj.bjp.0706944. Epub 2006 Dec 4.
5: Choi Y, Moon A, Kim YC. A pinusolide derivative, 15-methoxypinusolidic acid from Biota orientalis inhibits inducible nitric oxide synthase in microglial cells: implication for a potential anti-inflammatory effect. Int Immunopharmacol. 2008 Apr;8(4):548-55. doi: 10.1016/j.intimp.2007.12.010. Epub 2008 Jan 16. 61(6):519-22. doi: 10.1055/s-2006-959361. 25(5):249-58. 50(6):834-6. doi: 10.1248/cpb.50.834. 41(14):2626-30. doi: 10.1021/jm970569j. 16(16):4228-32. doi: 10.1016/j.bmcl.2006.05.077. Epub 2006 Jun 14. 37(11):e5726. doi: 10.1002/bmc.5726. Epub 2023 Aug 31. 33(7):1035-41. doi: 10.1007/s12272-010-0709-0. Epub 2010 Jul 27.
12:207. doi: 10.3389/fnagi.2020.00207.
合成参考文献
参考文献:10.1016/j.bmcl.2006.05.077
摘要:Shults EE, Velder J, Schmalz H-, Chernov SV, Rubalova TV, Gatilov YV, Henze G, Tolstikov GA, Prokop A. Gram-scale synthesis of pinusolide and evaluation of its antileukemic potential. Bioorganic & Medicinal Chemistry Letters. 2006 Aug;16(16):4228–32. doi: 10.1016/j.bmcl.2006.05.077.
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