Abstract:The present article describes a series of 21 N '-benzylidene-2-oxo-2H-chromene-3-carbohydrazides 4a-4v, which were synthesized and evaluated for their cell viabilities in non-infected and Mycobacterium bovis Bacillus Calmette-Guerin-infected macrophages. Subsequently, the non-cytotoxic compounds 4c, 4g, 4h, 4j, 4l and 4t were assessed against Mycobacterium tuberculosis ATCC 27294 using the microplate Alamar Blue assay and the activity expressed as the minimum inhibitory concentration in μg/mL. These compounds … Show more
“…We have identified another main product, confirmed as malohydrazide ( 4 ), besides salicylaldehyde azine ( 3 ) which was reported by Soliman et al in 1985 [ 38 ] as the sole product of the title reaction. Whereas the observations of this investigation have confirmed the identity of salicylaldehyde azine ( 3 ) and malonohydrazide ( 4 ), as the compounds produced through the reaction of ester 1 with hydrazine hydrate, the structures of products claimed to be formed from hydrazide 2 in investigations reported over the last two decades [ 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 ] need to be reassigned. Moreover, we described an efficient synthetic route for our targeted hydrazones 6a – f .…”
Section: Discussionmentioning
confidence: 61%
“…The contradictory data reported in last two decades [ 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 ], alerted us to be careful in our preparation of hydrazide 2 , for instance the hours of reflux used in the title reaction were 2 h [ 28 , 33 ], 3 h [ 29 ], 4 h [ 30 ], 6 h [ 27 , 36 ] and 10 h [ 26 , 34 ], and afforded different yields of the claimed hydrazide 2 : 99% [ 25 ], 90% [ 26 ], 80% [ 27 , 28 , 29 , 30 ], 72% [ 32 ], 65% [ 31 ] and 62% [ 34 ]. Moreover, different melting points have been reported for the claimed hydrazide 2 (m.p.…”
Section: Resultsmentioning
confidence: 99%
“…On the other hand, there is a great deal of interest in chromene-2-ones, especially 3-substituted derivatives, due to their important pharmacological effects, including analgesic, anti-arthritis, anti-inflammatory, anti-pyretic, anti-viral, anti-cancer and anticoagulant properties [ 13 , 14 , 15 ]. In the light of previous data and in continuation of our interest in the chemistry of hydrazides [ 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 ], our efforts targeted the synthesis of hydrazide 2 through the title reaction according to the literature methods [ 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 ], with the intention of subsequently treating hydrazide 2 with different aldehydes to obtain hydrazones 6a – f for our biological screening program. We report herein the results achieved to this end.…”
Although salicylaldehyde azine (3) was reported in 1985 as the single product of the reaction of ethyl 2-oxo-2H-chromene-3-carboxylate (1) with hydrazine hydrate, we identified another main reaction product, besides 3, which was identified as malono-hydrazide (4). In the last two decades, however, some articles have claimed that this reaction afforded exclusively hydrazide 2 and they have reported the use of this hydrazide 2 as a precursor in the syntheses of several heterocyclic compounds and hydrazones 6. We reported herein a study of the formation of 2 and a facile route for the synthesis of the target compounds N'-arylidene-2-oxo-2H-chromene-3-carbohydrazides 6a–f.
“…We have identified another main product, confirmed as malohydrazide ( 4 ), besides salicylaldehyde azine ( 3 ) which was reported by Soliman et al in 1985 [ 38 ] as the sole product of the title reaction. Whereas the observations of this investigation have confirmed the identity of salicylaldehyde azine ( 3 ) and malonohydrazide ( 4 ), as the compounds produced through the reaction of ester 1 with hydrazine hydrate, the structures of products claimed to be formed from hydrazide 2 in investigations reported over the last two decades [ 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 ] need to be reassigned. Moreover, we described an efficient synthetic route for our targeted hydrazones 6a – f .…”
Section: Discussionmentioning
confidence: 61%
“…The contradictory data reported in last two decades [ 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 ], alerted us to be careful in our preparation of hydrazide 2 , for instance the hours of reflux used in the title reaction were 2 h [ 28 , 33 ], 3 h [ 29 ], 4 h [ 30 ], 6 h [ 27 , 36 ] and 10 h [ 26 , 34 ], and afforded different yields of the claimed hydrazide 2 : 99% [ 25 ], 90% [ 26 ], 80% [ 27 , 28 , 29 , 30 ], 72% [ 32 ], 65% [ 31 ] and 62% [ 34 ]. Moreover, different melting points have been reported for the claimed hydrazide 2 (m.p.…”
Section: Resultsmentioning
confidence: 99%
“…On the other hand, there is a great deal of interest in chromene-2-ones, especially 3-substituted derivatives, due to their important pharmacological effects, including analgesic, anti-arthritis, anti-inflammatory, anti-pyretic, anti-viral, anti-cancer and anticoagulant properties [ 13 , 14 , 15 ]. In the light of previous data and in continuation of our interest in the chemistry of hydrazides [ 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 ], our efforts targeted the synthesis of hydrazide 2 through the title reaction according to the literature methods [ 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 ], with the intention of subsequently treating hydrazide 2 with different aldehydes to obtain hydrazones 6a – f for our biological screening program. We report herein the results achieved to this end.…”
Although salicylaldehyde azine (3) was reported in 1985 as the single product of the reaction of ethyl 2-oxo-2H-chromene-3-carboxylate (1) with hydrazine hydrate, we identified another main reaction product, besides 3, which was identified as malono-hydrazide (4). In the last two decades, however, some articles have claimed that this reaction afforded exclusively hydrazide 2 and they have reported the use of this hydrazide 2 as a precursor in the syntheses of several heterocyclic compounds and hydrazones 6. We reported herein a study of the formation of 2 and a facile route for the synthesis of the target compounds N'-arylidene-2-oxo-2H-chromene-3-carbohydrazides 6a–f.
“…reported a series of N -benzylidene-2-oxo-2H-chromene-3-carbohydrazides as substituents at the third position of coumarin, and examined their non-infected cell viabilities and anti-TB performance against M. tb , and the results are compared to pyrazinamide (PZA), which is a first-line anti-TB drug. Compound ( 5 ) in figure 1 exhibited an antimycobacterial activity at 50 mg ml −1 and was found more active than the reference drug PZA [ 42 ]. Figure 1.…”
Recently, heterogeneous catalysts have been explored eximiously in the synthesis of heterocyclic compounds. Therefore, here we used solid-supported heterogeneous silica sulfuric acid as a catalyst for the synthesis of Schiff's base of 3-chloroformylcoumarin in view of simplified procedure, reusability and acceptable efficiency, which are required in organic synthesis. An efficient and facile methodology is preferred for synthesis of a class of chromeno-3-substituted derivatives (1a–1l) with good yields. The molecular docking results showed excellent binding interactions with the Mycobacterium tuberculosis InhA-D148G mutant (PDB: 4DQU). The same biomolecules were screened for their in vitro anti-tubercular activity against the M.tb H37Rv strain and antimicrobial studies. Physico-chemistry, toxicity prediction with IC50 value and bioactivity score were also calculated for title compounds. Most active compounds were further tested for cytotoxicity studies and exhibited low-level cytotoxicity against Vero cells. The suggested conjugates are promising lead compounds for the subsequent investigation in search of new anti-tubercular agents. All the conjugates were obtained within the range and followed the Lipinski rule of 5, indicating more ‘drug-like’ nature.
“…possessing hydrazone moiety, akin to naturally occurring calanolide (8), have recently been screened against M. tuberculosis (9). Biodegradation of 2H-chromen-2-ones leads to in situ generation of carboxylic and phenolic -OH groups that might facilitate the penetration through the cell wall of the bacterial species (10).…”
1,4-Disubstituted bis-chromenyl triazole hybrids 5a-m have been synthesized in a three-step reaction sequence from 4-(bromomethyl)-2H-chromen-2-ones 3a-m. The intermediate azides 4a-m underwent a regioselective 1,3-dipolar cycloaddition with a 2H-chromen-2-one linked acetylenic dipolarophile in the presence of Cu (II)/ascorbate/ water/n-butanol reaction medium. Three compounds 5h-j exhibited 6.25 lg/mL MIC against M. tuberculosis. Among the compounds screened for antifungal activity, lowest MIC of 6.25 lg/mL was observed for 5c against A. niger that also exhibited DNA cleavage observed by agarose gel electrophoresis. All the compounds were moderately active against both Gram-positive and Gramnegative bacterial strains. The cytotoxic effect of potent compounds on normal cells (V79 and HBL100) was assessed by MTT assay.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.
