18740-44-8

Upstream product

• 75-15-0 carbon disulfide 
• 4651-82-5 2-amino-3-cyanothiophene 
• 56844-43-0 2-chlorothieno-[2,3-d]-pyrimidin-4(3H)-one 
• 18740-38-0 1H-thieno[2,3-d]pyrimidine-2,4-dione 
• 4651-81-4 Methyl 2-aminothiophene-3-carboxylate 
• 18740-39-1 2,4-dichlorothieno[2,3-d]pyrimidine 

Downstream Products

• 130750-43-5 2,4-diamino-6<<3-(trifluoromethyl)phenyl>thio>thieno<2,3-d>pyrimidin 
• 130750-46-8 2,4-diamino-6<<3-(trifluoromethyl)phenyl>sulfinyl>thieno<2,3-d>pyrimidin 
• 130750-42-4 2,4-diaminothieno<2,3-d>pyrimidin 

Relevant academic research and scientific papers

Novel 2,4-disubstituted quinazoline analogs as antibacterial agents with improved cytotoxicity profile: Modification of the benzenoid part

Bacterial resistance to currently used antibiotics demands the development of novel antibacterial agents with good safety margins and sufficient efficacy against multi-drug resistant isolates. We have previously described the synthesis of N-butyl-2-(butylthio)quinazolin-4-amine (I) as an optimized hit with broad-spectrum antibacterial activity and low cytotoxicity. In addition, we have identified a potential growing vector for this series of compounds. Herein, we describe further hit optimization which includes systematic diversifications of both the benzenoid part and the substituents at position 6 and 7 of compound I. Growing of the molecule beside the core modifications yielded several compounds with remarkable anti(myco)bacterial activity against a panel of pathogenic bacteria, including drug-resistant strains. Compound 12 showed a 2–4 fold improvement in activity than I against S. aureus Newman, S. pneumoniae DSM-20566 and E. faecalis DSM-20478. The compounds also showed a good safety profile towards human HepG2 cells.

The Reaction of 2-Aminothiophene-3-carbonitriles with Heterocumulenes

The reaction of 2-aminothiophene-3-carbonitriles (1) with phenyl isothiocyanate does not yield the expected thienopyrimidine derivatives but the substituted dithienopyrimidopyrimid-7-thiones (4).The compounds 4 also may be synthesized from 1 and thiophosgene.Analogously, from 1 and phenyl isocyanate the substituted dithienopyrimidopyrimid-7-ones (9) arise in small yields.They are better obtainable from 1 and phosgene.Carbon disulphide reacts with 1 in pyridine to form a mixture of the thienopyrimid-2,4-dithione (10) and the condensed compound 4.The ratio of of products depends on the substituents in the 4,5-position of 1.The structures are investigated by n.m.r.-spectroscopy.