Synthesis and antiallergy activity of [1,3,4]thiadiazolo[3,2-a]-1,2,3-triazolo[4,5-d]pyrimidin-9 (3H)-one derivatives. I.

Abstract

A series of 6-substituted [1,3,4]thiadiazolo[3,2-a]-1,2,3-triazolo[4,5-d]pyrimidin-9(3H)-one derivatives 4a--z were synthesized from 5-substituted 1,3,4-thiadiazol-2-amines 5 by the following consecutive reactions: pyrimidine ring closure with bis(2,4,6-trichlorophenyl) malonate, nitration, chlorination, amination, hydrogenation and diazotization. The structure of 4 was confirmed by an alternate synthesis of 4, involving reaction of 5-substituted 2-azido-1,3,4-thiadiazole 13 with ethyl cyanoacetate, followed by the Dimroth rearrangement and ring closure. The antiallergic activities (anti-passive peritoneal anaphylaxis, anti-passive cutaneous anaphylaxis and anti-slow reacting substance of anaphylaxis activities) of the products were evaluated.

• Authors: N Suzuki, T Miwa, S Aibara, H Kanno, H Takamori, M Tsubokawa, Y Ryokawa, W Tsukada, S Isoda
• Journal: Chemical & pharmaceutical bulletin (Chem Pharm Bull (Tokyo)) Vol. 40 Issue 2 Pg. 357-63 (Feb 1992) ISSN: 0009-2363 [Print] Japan
• PMID: 1606631 (Publication Type: Journal Article)

Chemical References

• Pyrimidinones
• SRS-A
• Thiadiazoles
• Triazoles

Topics

• Anaphylaxis (drug therapy)
• Animals
• Male
• Passive Cutaneous Anaphylaxis (drug effects)
• Pyrimidinones (chemical synthesis, chemistry, pharmacology)
• Rats
• Rats, Inbred Strains
• SRS-A (antagonists & inhibitors)
• Thiadiazoles (chemical synthesis, chemistry, pharmacology)
• Triazoles (chemical synthesis, chemistry, pharmacology)