ChemicalBook--->CAS DataBase List--->57103-51-2

57103-51-2

57103-51-2 Structure

57103-51-2 Structure
IdentificationBack Directory
[Name]

Nauclefine
[CAS]

57103-51-2
[Synonyms]

Nauclefine
Indolo[2',3':3,4]pyrido[1,2-b][2,7]naphthyridin-5(7H)-one, 8,13-dihydro-
[Molecular Formula]

C18H13N3O
[MDL Number]

MFCD33549177
[MOL File]

57103-51-2.mol
[Molecular Weight]

287.32
Chemical PropertiesBack Directory
[Melting point ]

285-290°C
[Boiling point ]

616.8±55.0 °C(Predicted)
[density ]

1.46±0.1 g/cm3(Predicted)
[pka]

16.67±0.20(Predicted)
Hazard InformationBack Directory
[Description]

One of two closely related bases isolated from Nauclea latifolia, nauclefine forms yellow needles when recrystallized from EtOH. It gives an ultraviolet spectrum in EtOH having absorption maxima at 220,250,290,300,372 and 390 nm. The structure has been confirmed by total synthesis.
[Uses]

Nauclefine is an indole alkaloid isolated from Nauclea officinalis. Nauclefine acts as a PDE3A modulator to induce cancer cell apoptosis through a PDE3A-SLFN12-dependent death pathway[1].
[in vivo]

Nauclefine (5 mg/kg, intratumorally, once per day for 22 days) significantly reduces the overall growth of HeLa-luc cell tumors in female nude mice (Balb/c-nu) infected with HeLa cells, especially after treatment 6 Days later, the tumor volume is significantly reduced without causing any decrease in the body weight of the mice. Its inhibition of tumor growth depends on the expression of PDE3A and SLFN12[1].

[References]

Hotellier, Delaveau, Pousset, Phytochern., 14, 1403 (1975)
Total synthesis:
Kametani et al., 1. Org. Chern., 41, 2542 (1976)
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