135276-88-9

Upstream product

• 1694-92-4 2-Nitrobenzenesulfonyl chloride 
• 100-39-0 benzyl bromide 
• 135276-86-7 2-benzylthio-1,4,5,6-tetrahydropyrimidine hydrobromide 

Downstream Products

• 1621065-33-5 1-[2-(4-methoxyphenyl)ethyl]-1,2,3,4-tetrahydropyrimidino[1,2-b]1,2,4-benzothiadiazine 6,6-dioxide 
• 1621065-35-7 1-[2-(3,4-dimethoxyphenyl)ethyl]-1,2,3,4-tetrahydropyrimidino[1,2-b][1,2,4]benzothiadiazine 6,6-dioxide 
• 1621065-36-8 1-[2-(3,4,5-trimethoxyphenyl)ethyl]-1,2,3,4-tetrahydropyrimidino[1,2-b][1,2,4]benzothiadiazine 6,6-dioxide 

Relevant academic research and scientific papers

Synthesis and Biological Evaluation of N-[2-(4-Hydroxyphenylamino)-pyridin-3-yl]-4-methoxy-benzenesulfonamide (ABT-751) Tricyclic Analogues as Antimitotic and Antivascular Agents with Potent in Vivo Antitumor Activity

Benzopyridothiadiazepine (2a) and benzopyridooxathiazepine (2b) were modified to produce tricyclic quinazolinone 15-18 or benzothiadiazine 26-27 derivatives. These compounds were evaluated in cytotoxicity and tubulin inhibition assays and led to potent inhibitors of tubulin polymerization. N-[2(4-Methoxyphenyl)ethyl]-1,2-dihydro-pyrimidino[2,1-b]quinazolin-6-one (16a) exhibited the best in vitro cytotoxic activity (GI50 10-66.9 nM) against the NCI 60 human tumor cell line and significant potency against tubulin assembly (IC50 0.812 μM). In mechanism studies, 16a was shown to block cell cycle in G2/M phase and to disrupt microtubule formation and displayed good antivascular properties as inhibition of cell migration, invasion, and endothelial tube formation. Compound 16a was evaluated in C57BL/6 mouse melanoma B16F10 xenograft model to validate its antitumor activity, in comparison with reference ABT-751 (1). Compound 16a displayed strong in vivo antitumor and antivascular activities at a dose of 5 mg/kg without obvious toxicity, whereas 1 needed a 10-fold higher concentration to reach similar effects.

STUDIES ON 1,2,4-BENZOTHIADIAZINE 1,1-DIOXIDES VII AND QUINAZOLINONES IV: SYNTHESIS OF NOVEL BUILT-IN HYDROXYGUANIDINE TRICYCLES AS POTENTIAL ANTICANCER AGENTS

Two representative built-in hydroxyguanidine tricycles containing 1,2,4-benzothiadiazine 1,1-dioxides (3) and quinazolinones (4) were prapared by reductive cyclization of 1-(2-nitrophenylsulfonyl)-2-benzylthio-2-imidazoline (9a), 1-(2-nitrophenylsulfonyl)

1,2,4-BENZOTHIADIAZINE 1,1-DIOXIDE. V: SYNTHESIS OF BUILT-IN HYDROXYGUANIDINE TRICYCLES AS POTENTIAL ANTICANCER AGENTS

Two representative built-in hydroxyguanidine tricycles, 10-N-hydroxy-2,3-dihydroimidazobenzothiadiazine 5,5-dioxide (1a) and 11-N-hydroxy-2,3-dihydro-4H-pyrimidobenzothiadiazine 6,6-dioxide (1b), were obtained in 78percent and