61863-68-1

Upstream product

• 96-50-4 2-thiazolylamine 
• 555-16-8 4-nitrobenzaldehdye 
• 69982-05-4 N-(1,3-thiazol-2-yl)triphenyliminophosphorane 
• 107866-76-2 C-(4-Nitro-phenyl)-N,N'-bis-thiazol-2-yl-methanediamine 
• 170703-18-1 2-(sulphinylamino)thiazole 

Downstream Products

• 96-50-4 2-thiazolylamine 
• 555-16-8 4-nitrobenzaldehdye 
• 95893-60-0 7-(4-Nitro-phenyl)-thiazolo[3,2-a]pyrimidin-5-one 
• 95893-58-6 6-Chloro-7-(4-nitro-phenyl)-thiazolo[3,2-a]pyrimidin-5-one 
• 95893-59-7 7-(4-Nitro-phenyl)-6-phenyl-thiazolo[3,2-a]pyrimidin-5-one 
• 61820-71-1 7-(4-nitro-phenyl)-6,6-diphenyl-6,7-dihydro-thiazolo[3,2-a]pyrimidin-5-one 

Relevant academic research and scientific papers

Development of 1,3-thiazole analogues of imidazopyridines as potent positive allosteric modulators of GABAA receptors

Structure–activity relationship studies were conducted in the search for 1,3-thiazole isosteric analogs of imidazopyridine drugs (Zolpidem, Alpidem). Three series of novel γ-aminobutyric acid receptor (GABAAR) ligands belonging to imidazo[2,1-b]thiazoles, imidazo[2,1-b][1,3,4]thiadiazoles, and benzo[d]imidazo[2,1-b]thiazoles were synthesized and characterized as active agents against GABAAR benzodiazepine-binding site. In each of these series, potent compounds were discovered using a radioligand competition binding assay. The functional properties of highest-affinity compounds 28 and 37 as GABAAR positive allosteric modulators (PAMs) were determined by electrophysiological measurements. In vivo studies on zebrafish demonstrated their potential for the further development of anxiolytics. Using the OECD “Fish, Acute Toxicity Test” active compounds were found safe and non-toxic. Structural bases for activity of benzo[d]imidazo[2,1-b]thiazoles were proposed using molecular docking studies. The isosteric replacement of the pyridine nuclei by 1,3-thiazole, 1,3,4-thiadiazole, or 1,3-benzothiazole in the ring-fused imidazole class of GABAAR PAMs was shown to be promising for the development of novel hypnotics, anxiolytics, anticonvulsants, and sedatives drug-candidates.

Synthesis and biological evaluation of benzo[d]isothiazole, benzothiazole and thiazole Schiff bases

Three new series of benzo[d]isothiazole, benzothiazole and thiazole Schiff bases were synthesized and tested in vitro with the aim of identifying novel lead compounds active against emergent and re-emergent human and cattle infectious diseases (AIDS, hepatitis B and C, tuberculosis, bovine viral diarrhoea) or against drug-resistant cancers (leukaemia, carcinoma, melanoma, MDR tumors) for which no definitive cure or efficacious vaccine is available at present. In particular, these compounds were evaluated in vitro against representatives of different virus classes, such as a HIV-1 (Retrovirus), a HBV (Hepadnavirus) and the single-stranded RNA+ viruses Yellow fever virus (YFV) and Bovine viral diarrhoea virus (BVDV), both belonging to Flaviviridae. Title compounds were also tested against representatives of Gram-positive and Gram-negative bacteria (Staphylococcus aureus, Salmonella spp.), various atypic mycobacterial strains (Mycobacterium fortuitum and Mycobacterium smegmatis), yeast (Candida albicans) and mould (Aspergillus fumigatus). None of the compounds showed antiviral or antimicrobial activity. The benzo[d]isothiazole compounds showed a marked cytotoxicity (CC 50=4-9 μM) against the human CD4+ lymphocytes (MT-4) that were used to support HIV-1 growth. For this reason, the most cytotoxic compounds of this series were evaluated for their antiproliferative activity against a panel of human cell lines derived from haematological and solid tumors. The results highlighted that all the benzo[d]isothiazole derivatives inhibited the growth of leukaemia cell lines, whereas only one of the above mentioned compounds (1e) showed antiproliferative activity against two solid tumor-derived cell lines.

Cycloaddition Reactions and other Reactions of 2-(Sulphinylamino)thiazole

2-(Sulphinylamino)thiozole (1) on reaction with some dienes under Diels-Alder condition gave the cycloaddition products (2a,b).Compound 1 also underwent reaction with nitrile oxide to form 3H-1,2,3,5-oxathiadiazole-2-oxide (3).The reactivity of 1 tow

Formation of azomethines from 2-aminothiazoles and (heterocyclic) aromatic aldehydes

Reexamination of previous work and new studies show that the reactions of 2-aminothiazoles with (heterocyclic) aromatic aldehydes are not straightforward; there are wide divergencies in behaviour between the various amine-aldehyde pairs. Simple efficient

CONDENSATION REACTIONS BETWEEN AROMATIC ALDEHYDES AND SOME HETEROCYCLIC AROMATIC AMINES

1,1-Diamino derivatives are obtained by means of reactions between 2-aminothiazole and aromatic aldehydes carried out in methanol (and in dimethyl sulphoxide).The reaction of amine with the C=N of imine occurs without catalyst and is an easier process than its addition to C=O.This behaviour is also displayed by a number of aromatic heterocycles and homocyclic amines and may be explained by considering the activating effect of the electron-withdrawing group present in the imine moiety.