20198-18-9

Upstream product

• 5900-58-3 2-amino-4-chloro-benzoic acid methyl ester 
• 1184-90-3 aminoiminomethanesulfonic acid 
• 4743-17-3 5-Chloroisatoic anhydride 
• 14527-26-5 2-methylisothiourea sulphate 
• 147895-43-0 S-methylisothiourea hemisulphate 
• 40928-13-0 4-chloroisatoic anhydride 
• 6828-35-9 5-chloro-2-iodoaniline 

Relevant academic research and scientific papers

A new reaction of aminoiminomethanesulfonic acid with methyl anthranilates

A new double guanidinylation and cyclization reaction of aminoiminomethanesulfonic acid with methyl anthranilates to yield 5H- quinazolino[3,2-a]quinazoline-5,12 (6H)-diones is described.

Conformationally-restricted analogues and partition coefficients of the 5-HT3 serotonin receptor ligands meta-Chlorophenylbiguanide (mCPBG) and meta-Chlorophenylguanidine (mCPG)

The present investigation examined two features of arylbiguanide and arylguanidine 5-HT3 ligands: conformation and partition coefficients. Several conformationally-constrained analogues of mCPBG (2) and mCPG (11; Ki=32 nM) were prepared and of these only 2-amino-5-chloro-3,4-dihydroquinazoline (14; Ki=34 nM) retained high affinity. The partition coefficient of compound 11 (LogPapp=-0.64) was less than that of its corresponding arylbiguanide 2 (LogPapp=-0.38). The quinazoline structure may represent a pharmacologically-active conformation of these agents, and the arylbiguanides were found more lipid soluble than their arylguanidine counterparts at physiological pH.

Synthesis of 2-Aminoquinazolinones via Carbonylative Coupling of ortho-Iodoanilines and Cyanamide

Herein, we describe a convenient and efficient synthesis of 2-aminoquinazolin-4(3H)-ones and N1-substituted 2-aminoquinazolin-4(1H)-ones by a domino carbonylation/cyclization process. The reaction proceeds via carbonylative coupling of readily available ortho-iodoanilines with cyanamide followed by in situ ring closure of an N-cyanobenzamide intermediate. The products were easily isolated by precipitation in moderate to excellent yields for a wide range of substrates, making this a highly attractive method for the synthesis of 2-aminoquinazolinones.

QUINAZOLINE DERIVATIVES FOR THE TREATMENT OF VIRAL INFECTIONS AND FURTHER DISEASES

This invention relates to quinazoline derivatives, processes for their preparation, pharmaceutical compositions, and their use in therapy of disorders in which the modulation of toll-like-receptors is involved.

HETEROCYCLIC SUBSTITUTED 2-AMINO-QUINAZOLINE DERIVATIVES FOR THE TREATMENT OF VIRAL INFECTIONS

This invention relates to heterocyclic substituted 2-amino-quinazoline derivatives, processes for their preparation, pharmaceutical compositions, and their use in treating viral infections.

2-Amino-6-chloro-3,4-dihydroquinazoline: A novel 5-HT3 receptor antagonist with antidepressant character

2-Amino-6-chloro-3,4-dihydroquinazoline HCl (A6CDQ, 4) binds at 5-HT 3 serotonin receptors and displays antidepressant-like action in the mouse tail suspension test (TST). Empirically, 4 was demonstrated to be a 5-HT3 receptor antagonist (two-electrode voltage clamp recordings using frog oocytes; IC50 = 0.26 μM), and one that should readily penetrate the blood-brain barrier (log P = 1.86). 5-HT3 receptor antagonists represent a potential approach to the development of new antidepressants, and 4 is an example of a structurally novel 5-HT3 receptor antagonist that is active in a preclinical antidepressant model (i.e., the mouse TST).

QUINAZOLINE DERIVATIVES FOR THE TREATMENT OF VIRAL INFECTIONS AND FURTHER DISEASES

This invention relates to quinazoline derivatives, processes for their preparation, pharmaceutical compositions, and their use in therapy of disorders in which the modulation of toll - like - receptors is involved.