89781-72-6

Upstream product

• 886040-24-0 2-(1H-imidazol-1-yl)-6-methoxy-1,2,3,4-tetrahydronaphthalen-1-ol 
• 20933-24-8 2-bromo-6-methoxy-1-tetralone 
• 85928-59-2 2-(1H-imidazol-1-yl)-6-methoxy-3,4-dihydronaphthalen-1(2H)-one 
• 1078-19-9 6-methoxy-3,4-dihydro-1(2H)-naphthalenone 

Relevant academic research and scientific papers

Synthesis and evaluation of heteroaryl-substituted dihydronaphthalenes and indenes: Potent and selective inhibitors of aldosterone synthase (CYP11B2) for the treatment of congestive heart failure and myocardial fibrosis

In this study, the synthesis and biological evaluation of heteroaryl-substituted dihydronaphthalenes and indenes (1-16) is described. The compounds were tested for activity by use of human CYP11B2 expressed in fission yeast and V79 MZh cells and for selectivity by use of human CYP11B1, CYP17, and CYP19. The most active inhibitor was the 6-methoxydihydronaphthalene 4 (IC 50 = 2 nM), showing a Ki value of 1.3 nM and a competitive type of inhibition. The 5-methoxyindene 3 was found to be the most selective CYP11B2 inhibitor (IC50 = 4 nM; CYP11B1 IC50 = 5684 nM), which also showed only marginal inhibition of human CYP3A4 and CYP2D6. Docking and molecular dynamics studies using our homology-modeled CYP11B2 structure were performed to understand some structure-activity relationships. Caco-2 cell experiments revealed highly cell-permeable compounds, and metabolic studies with 4 using rat liver microsomes showed sufficient stability.

N-Imidazolyl derivatives of the naphthalene and chroman rings as thromboxane A2 synthase inhibitors

A series of N-imidazol-1-yl derivatives of 1,2-dihydronaphthalene, 1,2,3,4-tetrahydronaphthalene, 2H-1-benzopyran and some related compounds were synthesized and tested as inhibitors of thromboxane A2 synthase in ex vivo experiments with orally treated rats.Some compounds showed good activity which was confirmed in experiments in vitro in rabbit whole blood.Some structural requirements for significant TxA2 synthase inhibitory activity are discussed.The selected 5,6-dihydro-7-(1H-imidazol-1-yl)-2-naphthalene-carboxylic acid (compound 7) was conformationally analysed using the Sybyl molecular model system in comparison with dazoxiben.Compound 7 was further pharmacologically investigated and on the basis of its interesting activities in vitro, ex vivo and in vivo and its low toxicity was selected for clinical investigation.

N-Imidazolyl derivatives containing naphthalene or indene nucleus

Compounds of the formula (I) STR1 wherein the symbol represents a single or a double bond; Z completes a single bond or is a --CH2 -- group; each of R1, R2, R3 and R4, which may be the same or different is (a) hydrogen; hydroxy; halogen; cyano; C1 -C6 alkyl; C1 -C6 alkoxy; a C2 -C4 acyl or C2 -C4 acylamino group; --SR', --N(R') (R"), --CH2 OR', --COR or --CH2 COR, wherein R is OR' or --N(R') (R") and each of R' and R", being the same or different, is hydrogen or C1 -C6 alkyl; or (b) one of R1, R2, R3 and R4 is 5- tetrazolyl or a group selected from --COCH2 OR', --CH=C(R')-COR and --X-C(R') (R")-COR, wherein R, R' and R" are as defined above, and X is --O--, --S--, or --NH--, and the others are as defined above under (a); one of R5 and R6 is hydrogen and the other is hydrogen, C1 -C6 alkyl, C3 -C6 cycloalkyl, or a phenyl or pyridyl ring, wherein the phenyl or pyridyl ring is unsubstituted or substituted by one to three substituents chosen from hydroxy and C1 -C4 alkoxy; or pharmaceutically acceptable salts thereof exhibit pharmaceutical activity as vasodilators or blood platelet aggregation inhibitors. Additionally, these compounds and their pharmaceutically acceptable salts are useful in the treatment of migraine, diabetic microangeopathy, rheumatoid arthritis, hypertension, peptic ulcers, osteoporosis, angina pectoris, atherosclerosis and dislipidaemies.