Heterocyclic Variants of the Purine System. I. Derivatives of Thiazolo[5,4-e]-1,2,4-Triazine

1987 ◽  
Vol 40 (3) ◽  
pp. 491 ◽  
Author(s):  
NW Jacobsen ◽  
AE Philippides

Derivatives of the thiazolo [5,4-e]-1,2,4-triazine ring system were prepared from appropriate 6-acylamino-1,2,4-triazin-5(2H)-ones by thiation and cyclization with phosphorus pentasulfide. 5-Methylthio-1,2,4-triazin-6-amines also gave thiazolo [5,4-e]-1,2,4-triazine derivatives when treated with carbon disulfide or phenyl isothiocyanate.

1987 ◽  
Vol 40 (4) ◽  
pp. 693 ◽  
Author(s):  
NW Jacobsen ◽  
AE Philippides

.Some representative derivatives of the new thiazolo [4,5- e]-1,2,4-triazine ring system were prepared from 5-acylamino-1,2,4-triazin-6(1 H)-ones by heating with phosphorus pentasulfide in pyridine. Further derivatives of the biheterocyclo system were also made from 6-methylthio-1,2,4-triazin-5-amines by heating with carbon disulfide or phenyl isothiocyanate.


1993 ◽  
Vol 48 (4) ◽  
pp. 493-504 ◽  
Author(s):  
Wolfgang Dölling ◽  
Klaus Frost ◽  
Frank Heinemann ◽  
Helmut Hartung

Derivatives of (diphenylmethylene-amino) acetic acid 1-3 react in the presence of bases (NaH, t-BuONa) or under phase transfer conditions with carbon disulfide to give the corresponding ketene dithioacetals 4-11 after alkylation. Phenyl isothiocyanate and dicyclohexyl carbodiimide give rise to ketene-S,N- and N,N-acetals. Methyl 2-(diphenylmethyleneamino)-2-(1,3-dithiane-2-ylidene) acetate (7) was characterized by an X-ray structure determination. The compound has a 2-aza-1,3-butadiene fragment containing two well localized double bonds. The C=N-C=C group is significantly non-planar, the relevant torsion angle amounts to -103.5(3)°.


Molecules ◽  
2021 ◽  
Vol 26 (4) ◽  
pp. 1028
Author(s):  
Monnaya Chalermnon ◽  
Sarocha Cherdchom ◽  
Amornpun Sereemaspun ◽  
Rojrit Rojanathanes ◽  
Tanatorn Khotavivattana

Twelve derivatives of biguanide-derived 1,3,5-triazines, a promising class of anticancer agent, were synthesised and evaluated for their anticancer activity against two colorectal cancer cell lines—HCT116 and SW620. 2c and 3c which are the derivatives containing o-hydroxyphenyl substituents exhibited the highest activity with IC50 against both cell lines in the range of 20–27 µM, which is comparable to the IC50 of cisplatin reference. Moreover, the potential use of the calcium citrate nanoparticles (CaCit NPs) as a platform for drug delivery system was studied on a selected 1,3,5-triazine derivative 2a. Condition optimisation revealed that the source of citrate ions and reaction time significantly influence the morphology, size and %drug loading of the particles. With the optimised conditions, “CaCit-2a NPs” were successfully synthesised with the size of 148 ± 23 nm and %drug loading of up to 16.3%. Furthermore, it was found that the release of 2a from the synthesised CaCit-2a NPs is pH-responsive, and 2a could be control released under the acidic cancer environment. The knowledge from this study is perceptive for further development of the 1,3,5-triazine-based anticancer drugs and provide the platform for the incorporation of other drugs in the CaCit NPs in the future.


1966 ◽  
Vol 20 (3) ◽  
pp. 159-160 ◽  
Author(s):  
T. S. Herman

The effects of chlorine atoms on the fundamental frequencies of the s-triazine ring are discussed and the vibrational assignments in the region 1600–700 cm−1 are extended. The variation in the position of the C3N3-ring bending mode in the region near 810 cm−1 is discussed.


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