ChemInform Abstract: STUDIES ON ANTITUBERCULAR AND ANTIBACTERIAL AGENTS: PREPARATION OF 1‐(4‐AMINOBENZOYL)‐2‐BENZALHYDRAZINE AND 1‐(4‐(PHENYLTHIOUREIDO)BENZOYL)‐2‐SUBSTITUTED‐BENZALHYDRAZINE

Patel, J. M.; Dave, M. P.; Langalia, N. A.; Thaker, K. A.

doi:10.1002/chin.198526173

Cited by 4 publications

(5 citation statements)

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“…In details, reaction of ester 1 with hydrazine hydrate gave hydrazide 2 as described previously [ 57 , 65 ]. Hydrazones 3a – 3d were obtained through acid- catalyzed condensation of 2 with the corresponding aromatic aldehydes [ 66 – 70 ]. The final compounds 4a – 4i were prepared by treatment of 3a – 3d with different aromatic isocyanates or phenyl isothiocyanate [ 57 ].…”

Section: Methodsmentioning

confidence: 99%

“…The final compounds 4a – 4i were prepared by treatment of 3a – 3d with different aromatic isocyanates or phenyl isothiocyanate [ 57 ]. Synthesis and anti-bacterial activity of compound 4b have been reported earlier [ 66 ].…”

Section: Methodsmentioning

confidence: 99%

“…One-way ANOVA analysis with Tukey post test was performed [57,65]. Hydrazones 3a-3d were obtained through acidcatalyzed condensation of 2 with the corresponding aromatic aldehydes [66][67][68][69][70]. The final compounds 4a-4i were prepared by treatment of 3a-3d with different aromatic isocyanates or phenyl isothiocyanate [57].…”

Section: Chemistrymentioning

confidence: 99%

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Design and synthesis of novel ureido and thioureido conjugated hydrazone derivatives with potent anticancer activity

et al. 2022

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Background Compounds possessing urea/thiourea moiety have a wide range of biological properties including anticancer activity. On the other hand, taking advantage of the low toxicity and structural diversity of hydrazone derivatives, they are presently being considered for designing chemical compounds with hydrazone moiety in the field of cancer treatment. With this in mind, a series of novel ureido/thioureido derivatives possessing a hydrazone moiety bearing nitro and chloro substituents (4a–4i) have been designed, synthesized, characterized and evaluated for their in vitro cytotoxic effect on HT-29 human colon carcinoma and HepG2 hepatocarcinoma cell lines. Results Two compounds (4c and 4e) having the chloro phenylurea group hybridized with phenyl hydrazone bearing nitro or chloro moieties demonstrated potent anticancer effect with the IC50 values between 2.2 and 4.8 µM at 72 h. The mechanism of action of compound 4c was revealed in hepatocellular carcinoma cells as an inducer of apoptosis in a caspase-independent pathway. Conclusion Taken together, the current work presented compound 4c as a potential lead compound in developing future hepatocellular carcinoma chemotherapy drugs. Methods The compounds were synthesized and then characterized by physical and spectral data (FT-IR, 1H-NMR, 13C-NMR, Mass). The anticancer activity was assessed using MTT assay, flowcytometry, annexin-V, DAPI staining and Western blot analysis. Graphical Abstract

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Design and synthesis of novel ureido and thioureido conjugated hydrazone derivatives with potent anticancer activity

et al. 2022

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“…This drug plays an important role as a prophylactic agent against several viral diseases. Antitubercular effects have been shown with various 4-aminobenzoic acid substituted benzalhydrazones (5). Sriram and co-workers have recently reported antitubercular activity of several thiourea derivatives obtained from isonicotinoyl hydrazone (6).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and evaluation of antiviral, antitubercular and anticancer activities of some novel thioureas derived from 4-aminobenzohydrazide hydrazones

Çikla¹

2010

mpj

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“…Hydrazide hydrazone derivatives have been reported to have a wide variety of pharmacological activities, such as antibacterial, antifungal, antihelmintic, antitubercular, anticonvulsant and anti-inflammatory (1)(2)(3)(4)(5)(6)(7)(8)(9). According to the literature, the in vivo and in vitro metabolic pathways of hydrazide hydrazones have not been investigated in detail (10)(11)(12).…”

Section: Introductionmentioning

confidence: 99%

In vivo metabolism of 4-fluorobenzoic acid [(5-nitro-2-furanyl) methylene] hydrazide in rats

Gulerman

Oruç

Kartal

et al. 2000

Eur. J. Drug Metab. Pharmacokinet.

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It is known that substituted hydrazide hydrazone derivatives have several biological and pharmacological activities; there is limited literature on the metabolism of hydrazide hydrazones in rats. In our previous study, 4-fluorobenzoic acid [(5-nitro-2-furanyl)methylene]hydrazide (S) was found active against Staphylococcus aureus ATCC 29213. Therefore, we planned to study the in vivo metabolism of S in rats. The substrate was administered in doses of 50 mg/kg or 100 mg/kg intraperitoneally. Blood samples were collected at 0, 5, 15, 30, 45 min and 1, 1.5, 2, 4, 8, 12, 24, 48 h after administration. The substrate and its potential metabolites were separated using HPLC on a reverse phase system. 4-Fluorobenzoic acid and one unidentified metabolite were detected together with substrate.

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ChemInform Abstract: STUDIES ON ANTITUBERCULAR AND ANTIBACTERIAL AGENTS: PREPARATION OF 1‐(4‐AMINOBENZOYL)‐2‐BENZALHYDRAZINE AND 1‐(4‐(PHENYLTHIOUREIDO)BENZOYL)‐2‐SUBSTITUTED‐BENZALHYDRAZINE

Abstract: Das Hydrazid (I) reagiert mit den Aldehyden (II) zu den Hydrazonen (IIIa), die mit Phenylisothiocyanat zu den Thioharnstoffen (IIIb) umgesetzt werden.

Cited by 4 publications

References 0 publications

Design and synthesis of novel ureido and thioureido conjugated hydrazone derivatives with potent anticancer activity

Design and synthesis of novel ureido and thioureido conjugated hydrazone derivatives with potent anticancer activity

Synthesis and evaluation of antiviral, antitubercular and anticancer activities of some novel thioureas derived from 4-aminobenzohydrazide hydrazones

In vivo metabolism of 4-fluorobenzoic acid [(5-nitro-2-furanyl) methylene] hydrazide in rats

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