Products Cited in Publications Worldwide Arylnitro monocarbonyl curcumin analogues: Synthesis and in vitro antitubercular evaluation

Arylnitro monocarbonyl curcumin analogues: Synthesis and in vitro antitubercular evaluation

du Preez, Charne; Legoabe, Lesetja J.; Jordaan, Audrey; Jesumoroti, Omobolanle J.; Warner, Digby F.; Beteck, Richard M.

DOI: PMID:

Abstract

Curcumin is a natural product that has been reported to exhibit myriad pharmacol. properties, one of which is antitubercular activity. It demonstrates antitubercular activity by directly inhibiting Mycobacterium tuberculosis (M.tb) and also enhances immune responses that ultimately lead to the elimination of M.tb by macrophages. This natural product is, however, unstable, and several analogs, noticeably monocarbonyl analogs, have been synthesized to overcome this challenge. Curcumin and its monocarbonyl analogs reported so far exhibit moderate antitubercular activity in the range of 7 to 16 μM. Herein, we report a straightforward synthesis of novel monocarbonyl curcumin analogs, their antitubercular activity, and the structure-activity relationship. The hit compound from this study, 3a, exhibits potent MIC90 values in the range of 0.2 to 0.9 μM in both ADC and CAS media.

Keywords

analogues ; aryl nitro ; curcumin ; synthesis ; tuberculosis

Purchased from AmBeed

2-Nitrobenzaldehyde

A135348552-89-698%

2-Nitrobenzaldehyde

18.0/25g

Detail
Curcumin

A147405458-37-798%

Curcumin

15.0/25g

Detail
5-Nitro-2-furaldehyde

A169721698-63-598%

5-Nitro-2-furaldehyde

10.0/5g

Detail
3-Nitrobenzaldehyde

A19281799-61-697%

3-Nitrobenzaldehyde

21.0/100g

Detail

A114785430626-03-097%

(E)-4-(4-Chlorophenyl)but-3-en-2-one

280.0/100g

Detail

A150084730625-98-095%

(E)-4-(4-Nitrophenyl)but-3-en-2-one

171.0/1g

Detail

A16582491675220-86-698%

4-(3,5-Dichlorophenyl)but-3-en-2-one

/

Detail

A194629330625-99-198%

(E)-4-(3-Nitrophenyl)but-3-en-2-one

/

Detail