Liegeois, Jean Francois F.; Bruhwyler, Jacques; Damas, Jacques; Nguyen, Thuy Phuong; Chleide, Eric M. G.; Mercier, Michel G. A.; Rogister, Francoise A.; Delarge, Jacques E. published an article in Journal of Medicinal Chemistry. The title of the article was 《New pyridobenzodiazepine derivatives as potential antipsychotics: synthesis and neurochemical study》.Synthetic Route of C12H8ClN3O3 The author mentioned the following in the article:
The discovery of a new, safe, atypical antipsychotic remains an important challenge. To achieve this goal, a series of N-methylpiperazinopyrido[2,3-b][1,4]- and -[1,5]- and -pyrido[4,3-b][1,4]- and -[1,5]-benzodiazepines I (A = Y = N, B = CH, R1 = H, 8-, 9-Cl, 8-F, 8-Me, R2 = H, 3-Me, R3 = H, Me, CHO, X = C-NMP, NMP = N-methylpiperazino; A = X = N, B = CH, R1 = R2 = H, R3 = H, CHO, Y = C-NMP; A = CH, B = Y = N, R1 = R2 = R3 = H, X = C-NMP; A = CH, B = X = N, R1 = R2 = H, R3 = H, CHO) were synthesized. Thus, (chloropyridinyl)aminobenzamides II (R1 = H, 8-, 9-Cl, 8-F, 8-Me, R2 = H, Me) cyclized and were condensed with N-methylpiperazine to give I. The dopaminergic (D1, D2), serotonergic (5-HT2), and cholinergic (M) affinities, frequently remarked in the action mechanisms of antipsychotic drugs, were determined using their resp. in vitro receptor binding assays. All affinities were reduced for each compound Optimal substituents were found to be in the 2- or 8-position for the retention of affinities, while substitution at the 5-position by acyl or alkyl groups dramatically diminished binding affinities. Pyridobenzodiazepine derivatives, such as clozapine, were found to be inactive or only weakly effective against apomorphine-mediated stereotypes in rats. In an original and complex behavioral model developed in dogs and successfully used to differentiate distinct classes of psychotropic drugs and to discriminate between typical and atypical neuroleptic drugs, I (A = N, B = CH, R1 = 8-Cl, 8-Me, R2 = R3 = H, X = C-NMP, Y = N; A = N, B = CH, R1 = R2 = R3 = H, X = N, Y = C-NMP) showed most of the behavioral characteristics previously described for neuroleptics. Their neurochem. profiles, particularly their 5-HT2/D2 pKi ratios, were compatible with an atypical antipsychotic effect. In the experiment, the researchers used N-(2-Chloropyridin-3-yl)-2-nitrobenzamide(cas: 1028-86-0Synthetic Route of C12H8ClN3O3)
N-(2-Chloropyridin-3-yl)-2-nitrobenzamide(cas: 1028-86-0) belongs to anime. Many important products require amines as part of their syntheses. Methylamine is utilized in the production of the analgesic meperidine (trade name Demerol) and the photographic developer Metol (trademark), and dimethylamine is used in the synthesis of the antihistamine diphenhydramine (trade name Benadryl), the solvent dimethylformamide (DMF), and the rocket propellant 1,1-dimethylhydrazine. The synthesis of the insect repellent N,N-diethyl-m-toluamide (DEET) incorporates diethylamine while that of the synthetic fibre Kevlar requires aromatic amines.Synthetic Route of C12H8ClN3O3