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Synthesis and anticancer activity of thiosubstituted purines.

Kowalska A, Latocha M, Pluta K - Med Chem Res (2015)

Bottom Line: The azathioprine analogs (2a, 2b, and 3a) were more active than azathioprine against SBN-19 and C-32 cell lines.The sulfenamide and sulfonamide derivatives of purine were very weak active against tested cell lines.All studied thiopurines were less toxic than cisplatin.

View Article: PubMed Central - PubMed

Affiliation: Department of Organic Chemistry, School of Pharmacy with the Division of Laboratory Medicine, The Medical University of Silesia, Jagiellońska 4, 41-200 Sosnowiec, Poland.

ABSTRACT

New thiopurines with the propargylthio, pyrrolidinobutynylthio, sulfenamide, and sulfonamide groups in the pyrimidine ring were synthesized. The anticancer activity of these compounds and previously obtained 2- or 6-substituted azathioprine analogs and dialkylaminoalkylthiopurines were tested in vitro against three cell lines: glioblastoma SNB-19, melanoma C-32, and human ductal breast epithelial tumor T47D. 2-Chloro-7-methyl-6-pyrrolidinobutynylthiopurine (5b) was the most potent compound against SBN-19 and C-32 cell lines with the activity similar to cisplatin (EC50 = 5.00 and 7.58 μg/ml, respectively). The dialkylaminoalkylthio derivatives (4b, 4c, 4e, and 4f) showed good activity against SBN-19 cell line (EC50 < 10 μg/ml). The azathioprine analogs (2a, 2b, and 3a) were more active than azathioprine against SBN-19 and C-32 cell lines. The sulfenamide and sulfonamide derivatives of purine were very weak active against tested cell lines. All studied thiopurines were less toxic than cisplatin.

No MeSH data available.


Related in: MedlinePlus

Synthesis of amine 9, sulfenamide 10, and sulfonamide 8 derivatives of purines
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Sch2: Synthesis of amine 9, sulfenamide 10, and sulfonamide 8 derivatives of purines

Mentions: Two-step synthesis of purinesulfonamide 8 via oxidation and chlorination of sulfide 6 with chlorine in acetic acid and subsequent transformation of sulfonyl chloride 7 with ammonia, diethylamine, or aniline failed. In this case, the highly instable chlorosulfonyl group lost sulfur dioxide, and resulted chloropurine reacted with ammonia and amines to give 2-chloro-6-amine derivatives 9a–c with 71–86 % yield (Scheme 2).Scheme 2


Synthesis and anticancer activity of thiosubstituted purines.

Kowalska A, Latocha M, Pluta K - Med Chem Res (2015)

Synthesis of amine 9, sulfenamide 10, and sulfonamide 8 derivatives of purines
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4491105&req=5

Sch2: Synthesis of amine 9, sulfenamide 10, and sulfonamide 8 derivatives of purines
Mentions: Two-step synthesis of purinesulfonamide 8 via oxidation and chlorination of sulfide 6 with chlorine in acetic acid and subsequent transformation of sulfonyl chloride 7 with ammonia, diethylamine, or aniline failed. In this case, the highly instable chlorosulfonyl group lost sulfur dioxide, and resulted chloropurine reacted with ammonia and amines to give 2-chloro-6-amine derivatives 9a–c with 71–86 % yield (Scheme 2).Scheme 2

Bottom Line: The azathioprine analogs (2a, 2b, and 3a) were more active than azathioprine against SBN-19 and C-32 cell lines.The sulfenamide and sulfonamide derivatives of purine were very weak active against tested cell lines.All studied thiopurines were less toxic than cisplatin.

View Article: PubMed Central - PubMed

Affiliation: Department of Organic Chemistry, School of Pharmacy with the Division of Laboratory Medicine, The Medical University of Silesia, Jagiellońska 4, 41-200 Sosnowiec, Poland.

ABSTRACT

New thiopurines with the propargylthio, pyrrolidinobutynylthio, sulfenamide, and sulfonamide groups in the pyrimidine ring were synthesized. The anticancer activity of these compounds and previously obtained 2- or 6-substituted azathioprine analogs and dialkylaminoalkylthiopurines were tested in vitro against three cell lines: glioblastoma SNB-19, melanoma C-32, and human ductal breast epithelial tumor T47D. 2-Chloro-7-methyl-6-pyrrolidinobutynylthiopurine (5b) was the most potent compound against SBN-19 and C-32 cell lines with the activity similar to cisplatin (EC50 = 5.00 and 7.58 μg/ml, respectively). The dialkylaminoalkylthio derivatives (4b, 4c, 4e, and 4f) showed good activity against SBN-19 cell line (EC50 < 10 μg/ml). The azathioprine analogs (2a, 2b, and 3a) were more active than azathioprine against SBN-19 and C-32 cell lines. The sulfenamide and sulfonamide derivatives of purine were very weak active against tested cell lines. All studied thiopurines were less toxic than cisplatin.

No MeSH data available.


Related in: MedlinePlus