N-Benzyl Derivatives of Leucine Esters

Popova, L. A.; Yurashevich, N. Ya.; Knizhnikov, V. A.

doi:10.1023/b:rujo.0000034963.96456.70

Cited by 5 publications

(1 citation statement)

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“…The Schiff bases 3t and 3v were made from 2c by treating them with furfural and salicylaldehyde, respectively, following a reported procedure. 16 The Schiff base 3t was reduced using sodium borohydride to form the alkylated thiazole 3u . The aminothiazoles ( 2a–2m ) were further converted to the intermediates N' , N' -dimethylamidines 3a to 3m by refluxing with DMF-dimethylacetal.…”

Section: Chemistrymentioning

confidence: 99%

Analogs of N′-hydroxy-N-(4H,5H-naphtho[1,2-d]thiazol-2-yl)methanimidamide inhibit Mycobacterium tuberculosis methionine aminopeptidases

Bhat¹,

Olaleye²,

Meyer³

et al. 2012

Bioorganic & Medicinal Chemistry

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Our previous target validation studies established that inhibition of methionine aminopeptidases (MtMetAP, type 1a and 1c) from Mycobacterium tuberculosis (Mtb) is an effective approach to suppressing Mtb growth in culture. A novel class of MtMetAP1c inhibitors comprising of N'-hydroxy-N-(4H,5H-naphtho[1,2-d]thiazol-2-yl)methanimidamide (4c) was uncovered through a high-throughput screen (HTS). A systematic structure—activity relationship study (SAR) yielded variants of the hit, 4b, 4h, and 4k, bearing modified A- and B-rings as potent inhibitors of both MtMetAPs. Except methanimidamide 4h that showed a moderate Mtb inhibition, a desirable minimum inhibitory concentration (MIC) was not obtained with the current set of MtMetAP inhibitors. However, the SAR data generated thus far may prove valuable for further tuning of this class of inhibitors as effective anti-tuberculosis agents.

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