| Identification | Back Directory | [Name]
(S)-9,11,12,13,13a,14-Hexahydro-2,3,6,7-tetramethoxydibenzo(f,h)pyrrol o(1,2-b)isoquinoline | [CAS]
482-20-2 | [Synonyms]
NSC 76387
NSTP 0G01
Tylophorin
NSC 717335
tylophorine
(+)-(S)-Tylophorine
6,7,10,11-Tetramethoxy-2,3-trimethylene-1,2,3,4-tetrahydrodibenzo[f,h]isoquinoline
9,11,12,13,13a,14-Hexahydro-2,3,6,7-tetramethoxydibenzo[f,h]pyrrolo[1,2-b]isoquinoline
(S)-9,11,12,13,13a,14-Hexahydro-2,3,6,7-tetramethoxydibenzo(f,h)pyrrol o(1,2-b)isoquinoline
(13aS)-9,11,12,13,13a,14-Hexahydro-2,3,6,7-tetraMethoxydibenzo[f,h]pyrrolo[1,2-b]isoquinoline
Dibenzo[f,h]pyrrolo[1,2-b]isoquinoline, 9,11,12,13,13a,14-hexahydro-2,3,6,7-tetramethoxy-, (13aS)- | [Molecular Formula]
C24H27NO4 | [MDL Number]
MFCD28899089 | [MOL File]
482-20-2.mol | [Molecular Weight]
393.48 |
| Chemical Properties | Back Directory | [Melting point ]
125-130 °C (decomp) | [alpha ]
D23 +15° (c = 0.7 in chloroform); D21 +73° (c = 0.7 in chloroform) | [Boiling point ]
559.9±45.0 °C(Predicted) | [density ]
1.26±0.1 g/cm3(Predicted) | [solubility ]
Chloroform (Slightly), Methanol (Slightly, Heated) | [form ]
Solid | [pka]
7.63±0.20(Predicted) | [color ]
Pale Yellow to Yellow |
| Hazard Information | Back Directory | [Description]
Tylophorine is an alkaloid first isolated in 1935 from plants of the genus Tylophora. Studies have demonstrated that this class of alkaloids, characterized by a phenanthroindolizidine skeleton, exhibits potent antitumor, anti-inflammatory, and antiviral activities. A representative tylophorine analogue, DCB-3503 (NSC-716802, 1), displayed an average GI?? value of approximately 10?? M against 59 human tumor cell lines in the National Cancer Institute (NCI) anticancer drug screening panel and also inhibited the proliferation of multidrug-resistant tumor cells. Tylocrebrine, another representative member of this class, advanced to Phase I clinical trials as a potential antitumor agent but was subsequently withdrawn because of severe neurotoxicity. Although extensive studies have investigated the antitumor mechanisms of tylophorine alkaloids, their direct molecular targets remain unclear.[1] | [Uses]
(+)-(S)-Tylophorine is a a major alkaloid of Tylophora indica. (+)-(S)-Tylophorine is an immunosuppressant and inflammation inhibitor. (+)-(S)-Tylophorine showed antiproliferative activity and induction of apoptosis in tumor cells. | [Definition]
ChEBI: Tylophorine is an organonitrogen heterocyclic compound and an organic heteropentacyclic compound. | [References]
[1] Liu, Yuxiu, et al. “6-OH-Phenanthroquinolizidine Alkaloid and Its Derivatives Exert Potent Anticancer Activity by Delaying S Phase Progression.” Journal of Medicinal Chemistry, 60 7, 2017, pp. 2764–79, https://doi.org/10.1021/acs.jmedchem.6b01502.
[2] Zeng, W., and S. Chemler. “Synthesis of (S)-(+)-Tylophorine.” Synfacts, 22 1, 2009, pp. 0004–0004, https://doi.org/10.1055/s-0028-1087241.
[3] Masal, Dattatraya P., and D. Srinivasa Reddy. “Gram-Scale Synthesis of (±)-Tylophorine.” Synlett, 55 1, 2024, https://doi.org/10.1055/a-2351-4828.
[4] Sotto, Antonella Di, et al. “Benzoindolizidine Alkaloids Tylophorine and Lycorine and Their Analogues with Antiviral, Anti-Inflammatory, and Anticancer Properties: Promises and Challenges.” Biomedicines, 11 10, 2023, https://doi.org/10.3390/biomedicines11102619. |
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