methyl (15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate

• ChemBase编号: 130407
• 分子式: C21H26N2O3
• 平均质量: 354.44274
• 单一同位素质量: 354.1943427
• SMILES: O=C(OC)[C@]1(O)n2c3c(c4ccccc24)CCN2CCC[C@](C1)(CC)[C@@H]32
• Canonical SMILES: COC(=O)[C@@]1(O)C[C@]2(CC)CCCN3[C@@H]2c2n1c1ccccc1c2CC3
• InChI: InChI=1S/C21H26N2O3/c1-3-20-10-6-11-22-12-9-15-14-7-4-5-8-16(14)23(17(15)18(20)22)21(25,13-20)19(24)26-2/h4-5,7-8,18,25H,3,6,9-13H2,1-2H3/t18-,20+,21+/m1/s1
• InChIKey: RXPRRQLKFXBCSJ-GIVPXCGWSA-N

名称和登记号

名称

• IUPAC标准名: methyl (15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo[9.6.2.0^2,^7.0^8,^1^8.0^1^5,^1^9]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate
• IUPAC传统名: minorin; methyl (15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo[9.6.2.0^2,^7.0^8,^1^8.0^1^5,^1^9]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate
• 别名: 长春胺; Vincamine; Vincamine; Vincamarine; Minorine; Pervincamine; Vincafor

登记号

• CAS号: 1617-90-9
• EC号: 216-576-3
• MDL号: MFCD00078054
• PubChem SID: 162224686; 24851332
• PubChem CID: 15376
• ATC码: C04AX07
• Chemspider ID: 14635
• IUPHAR配体索引: 349
• KEGG ID: D08677
• 美国药典/FDA物质标识码: 996XVD0JHT
• 维基百科标题: Vincamine

理论计算性质

• 可自由旋转的化学键: 3
• 里宾斯基五规则: true
• Acid pKa: 10.52077
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 1.896797
• LogD (pH = 7.4): 3.249398
• Log P: 3.3907504
• 摩尔折射率: 99.5741 cm^3
• 极化性: 40.111816 Å^3
• 极化表面积: 54.7 Å^2

分子性质

理化性质

• 熔点: 232 °C (dec.)(lit.)
• 比旋光度: [α]23/D +42.8°, c = 1 in pyridine

安全信息

• RTECS编号: YY8575000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22
• 安全公开号: 36
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

药理学性质

• 生物活性机理: Potent blockers of voltage-gated Na[+] channels

产品相关信息

• 纯度: 98%
• 生物来源: Alkaloid from Tabernaemontana rigida (Apocynaceae)
• 应用领域: Hypotensive; Vasodilator increasing blood flow to the brain
• Empirical Formula (Hill Notation): C21H26N2O3

详细说明

Sigma Aldrich - 194719

包装
1 g in glass bottle
250 mg in glass bottle

参考文献

• Aldrich Library of NMR Spectra, 2nd edn., 1983, 2, 942A, (nmr)
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 1066D, (ir)
• Schlittler, E. et al., Helv. Chim. Acta, 1953, 36, 2017, (isol, uv, ir)
• Trojnek, J. et al., Tet. Lett., 1961, 702, (uv, ir, struct)
• Plat, M. et al., Bull. Soc. Chim. Fr., 1962, 1082, (ms, uv)
• Mokry, J. et al., Tet. Lett., 1963, 999; 1917, (pmr, abs config, epimer)
• Hugel, G. et al., C. R. Hebd. Seances Acad. Sci. Ser. C, 1972, 274, 1350, (synth)
• Neuss, N. et al., Helv. Chim. Acta, 1973, 56, 2660, (cmr)
• Taylor, W.I. et al., The Vinca Alkaloids, M. Dekker, 1973, (pharmacol)
• Pfffli, P. et al., Helv. Chim. Acta, 1975, 58, 1131, (synth, pmr, uv, ir)
• Oppolzer, W. et al., Helv. Chim. Acta, 1977, 60, 1801, (synth)
• Gibson, K.H. et al., Tetrahedron, 1977, 33, 833, (synth)
• Rossey, G. et al., J.O.C., 1982, 47, 4745, (synth)
• Govindachari, T.R. et al., Indian J. Chem., Sect. B, 1983, 22, 531, (synth)
• Szabo, L. et al., Tetrahedron, 1983, 39, 3737, (synth)
• Vereczkey, L., Eur. J. Drug Metab. Pharmacokinet., 1985, 10, 89, (rev)
• Takano, S. et al., Chem. Comm., 1986, 156, (synth)
• Lounasmaa, M. et al., Heterocycles, 1986, 24, 1663, (synth)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 6203, (synonyms)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1427
• Nagy, T. et al., Heterocycles, 1997, 45, 2007-2013, (synth)
• Martin, G.E. et al., J. Het. Chem., 1997, 34, 695-699, (pmr, N-15 nmr)
• Schultz, A.G. et al., J.O.C., 1997, 62, 1223, (synth)
• Desmaele, D. et al., J.O.C., 1997, 62, 3890, (synth)
• Alves, J.C.F. et al., Tetrahedron: Asymmetry, 1999, 10, 297-306, (synth)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, VLF000