77434-52-7

Upstream product

• 29644-82-4 N-benzylidene-2-hydroxy-5-chloroaniline 
• 95-85-2 2-hydroxy-5-chloro-aniline 
• 100-52-7 benzaldehyde 

Downstream Products

• 77434-60-7 (4-Benzyl-6-chloro-3,4-dihydro-2H-benzo[1,4]oxazin-2-yl)-acetic acid methyl ester 
• 1417610-99-1 4-benzyl-6-chloro-3,4-dihydro-2H-1,4-benzoxazine 

Relevant academic research and scientific papers

Design, Synthesis, and Biological Activity of New N -(Phenylmethyl)-benzoxazol-2-thiones as Macrophage Migration Inhibitory Factor (MIF) Antagonists: Efficacies in Experimental Pulmonary Hypertension

Macrophage migration inhibitory factor (MIF) is a key pleiotropic mediator and a promising therapeutic target in cancer as well as in several inflammatory and cardiovascular diseases including pulmonary arterial hypertension (PAH). Here, a novel series of N-(phenylmethyl)-benzoxazol-2-thiones 5-32 designed to target the MIF tautomerase active site was synthesized and evaluated for its effects on cell survival. Investigation of structure-activity relationship (SAR) particularly at the 5-position of the benzoxazole core led to the identification of 31 that potently inhibits cell survival in DU-145 prostate cancer cells and pulmonary endothelial cells derived from patients with idiopathic PAH (iPAH-ECs), two cell lines for which survival is MIF-dependent. Molecular docking studies helped to interpret initial SAR related to MIF tautomerase inhibition and propose preferred binding mode for 31 within the MIF tautomerase active site. Interestingly, daily treatment with 31 started 2 weeks after a subcutaneous monocrotaline injection regressed established pulmonary hypertension in rats.

Increasing appendage diversity on 3,4-dihydro-3-oxo-2H-1,4-benzoxazines via Aphos-Pd(OAc)2-catalyzed Suzuki-Miyaura cross-coupling of aryl chlorides

A library of 32 members of 3,4-dihydro-3-oxo-2H-1,4-benzoxazines has been synthesized from two substituted 2-aminophenols via microwave-assisted one-pot regioselective annulation of 2-bromoalkanoates and subsequent Suzuki-Miyaura cross-coupling of the chloro-substituted scaffolds. The latter transformation was carried out using our Aphos-Pd(OAc)2 catalyst and the coupling of the aryl chlorides with arylboronic acids proceeded under mild reaction conditions at 60-80 C in THF-H2O (10:1) in the presence of K 3PO4·3H2O as the base to furnish the corresponding biaryl products in 80-98% yields.

One-pot regioselective annulation toward 3,4-dihydro-3-oxo-2H-1,4-benzoxazine scaffolds under controlled microwave heating

An efficient and general synthesis of 2-alkyl-3,4-dihydro-3-oxo-2H-1,4-benzoxazines under controlled microwave heating has been established. It consists of a microwave-assisted reductive N-arylmethylation of substituted 2-aminophenols with aromatic aldehy

Anti-allergic or anti-inflammatory substituted (hetero)-aralkylamino-ortho-phenols

Compounds of the general formula (I) or a pharmaceutically acceptable salt or solvate thereof;, wherein R1 is straight or branched C1-6alkyl, halo, nitro, cyano, hydroxy, or COR6 wherein R6 is straight or branch