New azetidine-3-carbonyl-N-methyl-hydrazino derivatives of fluoroquinolones: synthesis and evaluation of antibacterial and anticancer properties

Rajulu, G. Govinda; Naik, H.S. Bhojya; Kumar, Goutam; Sivakumar, Ramaraj; Sambasivam, Ganesh; Koppolu, Kesavan Poonimangadu

doi:10.1007/s00044-013-0873-0

Cited by 20 publications

(12 citation statements)

References 12 publications

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“…Compound 6h showed more potency against the MCF‐7 cell line with 56% growth inhibition as compared with the standard drugs ciprofloxacin (41% growth inhibition) and SAHA (33% growth inhibition). [ 42 ]…”

Section: Therapeutic Importance Of Molecules Containing the Azetidine Heterocyclementioning

confidence: 99%

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Azetidines of pharmacological interest

Parmar

Soni²,

Guduru

et al. 2021

Archiv der Pharmazie

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Azetidines are almost unexplored among nitrogen‐containing saturated heterocycles due to difficulties associated with their synthesis. However, over the past few years, attempts have been made by scientists to advance their synthetic feasibility. Compounds with the azetidine moiety display an important and diverse range of pharmacological activities, such as anticancer, antibacterial, antimicrobial, antischizophrenic, antimalarial, antiobesity, anti‐inflammatory, antidiabetic, antiviral, antioxidant, analgesic, and dopamine antagonist activities, and are also useful for the treatment of central nervous system disorders and so forth. Owing to its satisfactory stability, molecular rigidity, and chemical and biological properties, azetidine has emerged as a valuable scaffold and it has drawn the attention of medicinal researchers. The present review sheds light on the traditional method of synthesis of azetidine and advancements in synthetic methodology over the past few years, along with its application with various examples, and its biological significance.

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Section: Therapeutic Importance Of Molecules Containing the Azetidine Heterocyclementioning

confidence: 99%

“…However, all other compounds were less active than the standard drug SAHA in A549 and HCT‐116 cell lines and were more potent than ciprofloxacin in A549 and HCT‐116. [ 42 ]…”

Section: Therapeutic Importance Of Molecules Containing the Azetidine Heterocyclementioning

confidence: 99%

Azetidines of pharmacological interest

Parmar

Soni²,

Guduru

et al. 2021

Archiv der Pharmazie

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“…The fluoroquinolone series, substituted with N-(substituted azetidine-3-carbonyl)-N-methylhydrazino derivatives showed cytotoxic activity toward Breast cancer cell line, MCF-7, Colon cancer cell line, HCT-116, and Lung adenocarcinoma cell line, A549, and some of them exhibited higher activity than ciprofloxacin and the positive control drug SAHA. Compound 69 exhibited the highest activity among this series against MCF-7 breast cancer cell line with GI% range, 23-56 % at a concentration range 1-50 μM [103]. The norfloxacin analogs substituted at N-7 with benzo[d]thiazolyl moiety through butyramide linker were evaluated for the cytotoxic activities against A549, lung cancer cell line.…”

Section: Modifications Of Fluoroquinolones At 7positionmentioning

confidence: 99%

Recent Strategies in Design of Antitumor and Antibacterial Fluoroquinolones

Samir

Ramadan

Hamed

et al. 2021

Journal of advanced Biomedical and Pharmaceutical Sciences

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Fluoroquinolones are known widely used synthetic antibacterial agents. Generally, there were some obstacles associated with their therapeutic use. Moreover, many research studies all over the world proved the variable biological effects of fluoroquinolones such as antituberculosis, anticancer, or even antiviral activities. The current review is focused on modifications that occurred in the fluoroquinolone scaffold for their repositioning from antibacterial into anticancer agents especially modifications at C-7 or at the carboxylic C-3 groups. In addition, it includes the recent research studies carried out to improve the potency, spectrum of activity, or pharmacokinetics of antibacterial fluoroquinolones. Hence, this review may be useful for researchers in the design and synthesis of new fluoroquinolones with improved biological activities.

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“…Some derivatives revealed an activity more than the reference drug SAHA, which was used as a positive control. Compound 13 was among the most potent derivatives and exhibited the highest activity against the breast carcinoma MCF‐7 cell line with a percent growth inhibition 23–56% at a concentration range 1–50 µM . Derivatives of ciprofloxacin and norfloxacin substituted at the piperazinyl N‐ 4 with N‐ (benzo[ d ]thiazol‐2‐yl)butyramide substituents were tested for cytotoxicity using the human lung cancer cell lines A549.…”

Section: Fluoroquinolone Derivatives With Anticancer Activitymentioning

confidence: 99%

Towards anticancer fluoroquinolones: A review article

Abdel-AAl

Abdel‐Aziz

Shaykoon

et al. 2019

Archiv der Pharmazie

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Different studies about the anticancer potential of several medically used antibacterial fluoroquinolones have been established. Fluoroquinolone derivatives, like some anticancer drugs, such as doxorubicin, can achieve antitumor activity via poisoning of type II human DNA topoisomerases. Interestingly, structural features required for the anticancer activity of quinolones have been determined. Most of the chemical modifications required to convert antibacterially acting fluoroquinolones into their anticancer analogs were at position 7 and the carboxylic group at position 3. This review highlights the antitumor potential of fluoroquinolones in general and summarizes the chemical modifications carried out on fluoroquinolones to become anticancer agents. Moreover, the review gives a quick recap on metal ion chelates with fluoroquinolones and their substantial role in topoisomerase poisoning and antitumor potential improvement. Hence, it should be highly interesting for researchers attempting to design and synthesize novel anticancer fluoroquinolone candidates. K E Y W O R D S anticancer, DNA topoisomerase, metal ion complexes, quinolones Arch Pharm Chem Life Sci. 2019;352:1800376.wileyonlinelibrary.com/journal/ardp

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New azetidine-3-carbonyl-N-methyl-hydrazino derivatives of fluoroquinolones: synthesis and evaluation of antibacterial and anticancer properties

Cited by 20 publications

References 12 publications

Azetidines of pharmacological interest

Azetidines of pharmacological interest

Recent Strategies in Design of Antitumor and Antibacterial Fluoroquinolones

Towards anticancer fluoroquinolones: A review article

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