Studies on nitrophenothiazines. I. Their synthesis and an explanation for the peculiar behaviour of halonitrobenzenes with o-aminothiophenol

Hl, Sharma; Vn, Sharma; Mital, R. L.

doi:10.1071/ch9683081

Cited by 4 publications

(1 citation statement)

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“…The crude products 8g – o were washed with water or dilute ammonia to remove any remaining acetic acid for spontaneous oxidative cyclization to afford imine products 9g – o . Finally, replacement of the imine ( 9a – v ) with commercially available amines or amines ( N -isobutyl-4-aminopiperidine, N -methyl-4-aminopiperidine, 4-aminotetrahydropyrane, and 4-methoxycyclohexylamine) − prepared by known methods provided target compounds ( 10 – 78 ), , which were further purified via column chromatography or recrystallization. We found that a catalytic amount of glacial acetic acid could facilitate the final reaction and shorten the reaction time significantly.…”

Section: Chemistrymentioning

confidence: 99%

Identification of Less Lipophilic Riminophenazine Derivatives for the Treatment of Drug-Resistant Tuberculosis

Zhang

et al. 2012

J. Med. Chem.

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Clofazimine (CFZ), a member of the riminophenazine class, has been studied in clinical trials for the treatment of multidrug-resistant tuberculosis (MDR-TB). CFZ has several side effects which can be attributed to its extremely high lipophilicity. A series of novel riminophenazine analogues bearing a C-2 pyridyl substituent was designed and synthesized with the goal of maintaining potent activity against Mycobacterium tuberculosis (M. tuberculosis) while improving upon its safety profile by lowering the lipophilicity. All compounds were evaluated for their in vitro activity and cytotoxicity. The results demonstrated that many new compounds had potent activity against M. tuberculosis with MICs of less than 0.03 μg/mL and low cytotoxicity with IC(50) values greater than 64 μg/mL. Some compounds were tested for in vivo efficacy against MDR-TB in an experimental mouse infection model. Two compounds demonstrated equivalent or better efficacy than CFZ in this model with significantly reduced skin discoloration potential.

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