Design and synthesis of some novel 7-substituted thiosemicarbazinyl-quinolines via Ullmann coupling reaction and examination of their antimicrobial activities

Patel, Jankiben J.; Patel, Anuj P.; Chikhalia, Kishor H.

doi:10.1007/s11164-017-3136-8

Cited by 6 publications

(6 citation statements)

References 29 publications

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“…The thio‐semi‐carbazinyl‐quinolines series synthesis was done by Patel and coworkers through a modified Ullmann reaction. They performed in‐vitro studies in which compound 71 showed better antibacterial activities with MIC value of 62.5 μg/ml against S. pyogenus Gram‐positive bacteria and antifungal activity with MIC value of 100 μg/ml against C. Albicans (Patel et al, 2018). El‐Shershaby et al synthesized new quinoline derivative molecules, among them compound 72 displayed effective broad‐spectrum antimicrobial activity against the majority of the tested strains, such as microbes including two Gram‐positive bacteria ( S. pneumoniae and B. subtilis ), two Gram‐negative bacteria ( P. aeruginosa and E. coli ), and four fungal strains ( A. fumigatus , S. racemosum , G. candidum , and C. albicans ) with reported MIC values ranging from 0.66 to 3.98 μg/ml (El‐Shershaby et al, 2021).…”

Section: Biological Activitiesmentioning

confidence: 99%

Quinoline‐derivatives as privileged scaffolds for medicinal and pharmaceutical chemists: A comprehensive review

et al. 2022

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The quinoline scaffolds are privileged for their numerous biological activities in the pharmaceutical field. This moiety constitutes a well‐known space in several marketed preparations. The quinoline scaffolds gained attention in modern days being an important chemical moiety in the identification, designing, and synthesis of novel potent derivatives. The current review is developed to shine the light on critical and significant insights on the quinoline derivatives possessing diverse biological activities such as analgesic, anti‐inflammatory, antialzheimer, anti‐convulsant, anti‐oxidant, antimicrobial, anti‐cancer activities and so on. A detailed summary of quinoline ring from its origin to the recent advancements regarding its synthesis, green chemistry approaches, patented methods, and its marketed drugs is presented in the review. We attempted to review the literature compiling the critical information that has potential to encourage fellow researchers and scientists for the design and development of quinoline scaffold based active molecules that have improved therapeutic performance along with profound pharmacological properties.

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Section: Biological Activitiesmentioning

confidence: 99%

Quinoline‐derivatives as privileged scaffolds for medicinal and pharmaceutical chemists: A comprehensive review

et al. 2022

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“…Thiosemicarbazide at quinoline 7‐position in addition to morpholin‐1‐yl ring at 4‐position led to noteworthy antibacterial drug molecules. [ 25 ] In total, 10 derivatives have been prepared, wherein compound bearing phenyl ring via semicarbazide functionality has exhibited slightly reduced potency (MIC = 62.5 µg/ml) against S. aureus MTCC 96, compared with ciprofloxacin (MIC = 50 µg/ml), whereas its chloro analog resulted in a similar inhibitory property in case of S. pyogenus MTCC 443. Fortunately, compound 22 (Figure 5) possessing 3‐methylphenyl ring has exhibited the finest E. coli MTCC 442 inhibitory property as good as ciprofloxacin (MIC = 25 µg/ml).…”

Section: Antibacterial Activitymentioning

confidence: 99%

“…Good‐to‐potent antifungal activities have been exhibited by the 4‐morpholinoquinoline molecules derivatized with substituted aryl moieties tethered to quinoline 7‐position through thiosemicarbazide functionality. [ 25 ] The antifungal potencies of the evaluated derivatives revealed compound 110 (Figure 16) to possess a 3‐chlorophenyl ring as a significant C. albicans MTCC 227 inhibitor, comparable with nystatin (MIC = 100 µg/ml), whereas diminished inhibitory properties are noticed for the screened molecules against A. niger MTCC 282 and Aspergillus clavatus MTCC 1323 strains.…”

Section: Antifungal Activitymentioning

confidence: 99%

Recent update on antibacterial and antifungal activity of quinoline scaffolds

Dorababu¹

2020

Archiv der Pharmazie

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Although most of the heterocycles have been reported to possess a significant pharmacological activity, only a few of them, namely quinoline derivatives, have exhibited the finest biological activities. Despite the few medicinal properties of the plain quinoline molecule, its derivatives exhibit diverse pharmacological properties such as anticancer, anti‐inflammatory, antibacterial, antiviral, antifungal, antiprotozoal activities, and so on. The potential antimicrobial properties of the quinoline derivatives are evident from the decades of research on these derivatives. Owing to limitations like drug resistance, high cost, severe side effects, and less bioavailability of previously synthesized antimicrobial agents, these drugs have become obsolete in recent years. Hence, the design of more efficient antimicrobial drugs must be given topmost priority. A breakthrough in drug discovery is a must to prevent malevolent microbial diseases. Addressing all these issues, researchers have been continuously contributing to antimicrobial drug discovery. Herein, a short description of the pharmacology of antimicrobial agents such as antibacterials and antifungals synthesized recently is provided. The versatile derivatization of the quinoline moiety leading to significant antimicrobial potencies is discussed, considering the structure–activity relationship.

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“…On the other hand, 4-(6-amidoquinolin-2-yl)morpholine B is a potent MCH1R antagonist, implicated in body weight (obesity) regulation, a major contributor to the development of diseases, including type 2 diabetes mellitus, coronary heart disease, certain forms of cancer, and osteoarthritis [9]. Additionally, 4-(quinolin-4-yl)morpholine C exhibited some in vitro antibacterial activity [15].…”

Section: Introductionmentioning

confidence: 99%

Three-Step Synthesis of N-(7-chloro-4-morpholinoquinolin-2-yl)benzamide from 4,7-Dichloroquinoline

Aparicio Acevedo,

Ortiz Villamizar,

Kouznetsov

2024

Molbank

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The quinoline derivative, N-(7-chloro-4-morpholinoquinolin-2-yl)benzamide, was synthesized in a conventional three-step procedure from 4,7-dichloroquinoline using a N-oxidation reaction/C2-amide formation reaction/C4 SNAr reaction sequence. The structure of the compound was fully characterized by FT-IR, 1H-, 13C-NMR, DEPT-135°, and ESI-MS techniques. Its physicochemical parameters (Lipinski’s descriptors) were also calculated using the online SwissADME database. Such derivatives are relevant therapeutic agents exhibiting potent anticancer, antibacterial, antifungal, and antiparasitic properties.

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Design and synthesis of some novel 7-substituted thiosemicarbazinyl-quinolines via Ullmann coupling reaction and examination of their antimicrobial activities

Cited by 6 publications

References 29 publications

Quinoline‐derivatives as privileged scaffolds for medicinal and pharmaceutical chemists: A comprehensive review

Quinoline‐derivatives as privileged scaffolds for medicinal and pharmaceutical chemists: A comprehensive review

Recent update on antibacterial and antifungal activity of quinoline scaffolds

Three-Step Synthesis of N-(7-chloro-4-morpholinoquinolin-2-yl)benzamide from 4,7-Dichloroquinoline

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