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| | Tylophorine Basic information |
| Product Name: | Tylophorine | | Synonyms: | (S)-9,11,12,13,13a,14-Hexahydro-2,3,6,7-tetramethoxydibenzo(f,h)pyrrol o(1,2-b)isoquinoline;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;(13aS)-9,11,12,13,13a,14-Hexahydro-2,3,6,7-tetraMethoxydibenzo[f,h]pyrrolo[1,2-b]isoquinoline;NSC 717335;NSC 76387;NSTP 0G01;Tylophorin | | CAS: | 482-20-2 | | MF: | C24H27NO4 | | MW: | 393.48 | | EINECS: | | | Product Categories: | | | Mol File: | 482-20-2.mol |  |
| | Tylophorine Chemical Properties |
| Melting point | 125-130 °C (decomp) | | Boiling point | 559.9±45.0 °C(Predicted) | | alpha | D23 +15° (c = 0.7 in chloroform); D21 +73° (c = 0.7 in chloroform) | | 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 |
| | Tylophorine Usage And Synthesis |
| 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 GI₅₀ value of approximately 10⁻⁸ 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member of this class, advanced to Phase I clinical trials as a potential antitumor agent but was subsequently withdrawn because of severe neurotoxicity.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. |
| | Tylophorine Preparation Products And Raw materials |
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