Antimicrobial and Antileishmanial Studies of Novel (2E)-3-(2-Chloro-6-methyl/methoxyquinolin-3-yl)-1-(Aryl)prop-2-en-1-ones

Rizvi, Syed Umar Farooq; Siddiqui, Hamid Latif; Parvez, Masood; Ahmad, Matloob; Siddiqui, Waseeq Ahmad; Yasinzai, Muhammad Masoom

doi:10.1248/cpb.58.301

Cited by 22 publications

(11 citation statements)

References 43 publications

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“…In another study, focused on diphenylpropenones, derivatives with 3,5-dibromo or 3,5-bis(trifluoromethyl) substitution were the most active compounds [38]. In agreement with the positive effect of chlorine substitution in our series, the most antifungal and antibacterial substance in a 3-quinolinyl-1-thienyl propenones had so far three chlorine atoms [39]. Polyhalogenation of 3-phenyl-1-pyrrol-2-ylpropenones also positively reflected in their antimicrobial activity [40].…”

Section: Resultssupporting

confidence: 76%

Novel Halogenated Pyrazine-Based Chalcones as Potential Antimicrobial Drugs

et al. 2016

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Chalcones, i.e., compounds with the chemical pattern of 1,3-diphenylprop-2-en-1-ones, exert a wide range of bio-activities, e.g., antioxidant, anti-inflammatory, anticancer, anti-infective etc. Our research group has been focused on pyrazine analogues of chalcones; several series have been synthesized and tested in vitro on antifungal and antimycobacterial activity. The highest potency was exhibited by derivatives with electron withdrawing groups (EWG) in positions 2 and 4 of the ring B. As halogens also have electron withdrawing properties, novel halogenated derivatives were prepared by Claisen-Schmidt condensation. All compounds were submitted for evaluation of their antifungal and antibacterial activity, including their antimycobacterial effect. In the antifungal assay against eight strains of selected fungi, growth inhibition of Candida glabrata and Trichophyton interdigitale (formerly T. mentagrophytes) was shown by non-alkylated derivatives with 2-bromo or 2-chloro substitution. In the panel of selected bacteria, 2-chloro derivatives showed the highest inhibitory effect on Staphylococcus sp. In addition, all products were also screened for their antimycobacterial activity against Mycobacterium tuberculosis H37RV My 331/88, M. kansasii My 235/80, M. avium 152/80 and M. smegmatis CCM 4622. Some of the examined compounds, inhibited growth of M. kansasii and M. smegmatis with minimum inhibitory concentrations (MICs) comparable with those of isoniazid.

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Section: Resultssupporting

confidence: 76%

Novel Halogenated Pyrazine-Based Chalcones as Potential Antimicrobial Drugs

et al. 2016

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“…28. Recent work has confirmed the interesting antileishmanial properties of other quinoline series (2,6,18). In addition, quinolines have recently been found to inhibit leishmanial GDP-mannose-pyrophosphorylase, an enzyme system producing a range of mannose-rich glycoconjugates that are essential for parasite survival and virulence (7).…”

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confidence: 81%

In Vitro Activities of New 2-Substituted Quinolines against Leishmania donovani

Loiseau

Gupta

Verma

et al. 2011

Antimicrob Agents Chemother

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A series of 9 quinolines and 18 styrylquinolines was evaluated for the drugs' in vitro antileishmanial activities and cytotoxicities. The 7-aroylstyrylquinoline scaffold appeared to be the most promising one, with the most interesting compound, no. 35, exhibiting a 50% inhibitory concentration (IC 50 ) of 1.2 M and a selectivity index value of 121.5. Compound 35 was 10-fold and 8-fold more active than miltefosine and sitamaquine, the reference compounds, with selectivity indexes 607-fold and 60-fold higher, respectively.Leishmaniasis is a family of parasitic diseases that affect about 12 million people in tropical and subtropical areas in the form of three clinical expressions: visceral leishmaniasis, which is fatal in the absence of treatment; muco-cutaneous leishmaniasis; and cutaneous leishmaniasis, which is often selfcuring. Classical drugs such as antimonials (Pentostam and Glucantime) are toxic, and drug resistance is increasing dangerously in the field (3). A liposomal amphotericin B formulation (AmBisome) less toxic than amphotericin B deoxycholate is gradually becoming the first-line therapy, especially in immunocompromised patients, but this drug must be administered by a parenteral route (11). Miltefosine (Impavido) was the first drug registered against visceral leishmaniasis in the last decade; however, its toxicity and the appearance of drug resistance justify the search for new chemical series in order to find an orally safe and active drug (8).Quinolines substituted at the 2-position have shown in vivo activities against Leishmania donovani, and many compounds have been synthesized over the last decade (14). The Drug for Neglected Diseases Initiative (DNDi) has been considering this series for evaluation in preclinical development for about a year and a half. However, although promising, the series still requires improvements, and here we report the in vitro antileishmanial evaluation of new quinoline derivatives, including 2-[2-aryl(ethenyl)]-substituted quinoline (2-styrylquinolines) bearing additional aroyl/acyl groups at the C-7 position. In addition, some compounds within this series were recently shown to display substantial antiviral activity in HIV-infected cells (13,22).The synthesis of most of the compounds has been previously reported. Briefly, Kolbe carbonation of 8-hydroxyquinaldine afforded the pivotal hydroxyacid compound 1 (9), which was further elaborated into the 5-iodoquinaldine compound 12 and amide compound 17 (13). Similarly, bromination of the C-5 position and protection of the salicylic moiety provided 5-bromoquinaldine compound 2, which was engaged in a modified Suzuki cross-coupling reaction to give 5-arylated derivatives 14 to 16 (19). Styrylquinoline compounds 19 to 27 were prepared from the corresponding quinaldine compound 3 by Perkin-type condensation in refluxing acetic anhydride, followed by hydrolysis in a pyridine-water mixture (10,16,21,22). Finally, the 7-aroyl-stryryquinoline derivatives 28 to 35 were obtained via the 7-bromostyrylquinoline compound 5 accordin...

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“…Recently, the antibacterial activity of chalcones has been increasingly documented. Many research groups synthesized novel chalcones that possess antibacterial activity (Batovska et al, 2009;Nowakowska et al, 2008;Liu et al, 2008;Avila et al, 2008;Nielsen et al, 2005;Rizvi et al, 2010).…”

Section: Antibacterial Activitymentioning

confidence: 99%

Synthesis and crystal structure of chalcones as well as on cytotoxicity and antibacterial properties

Cai²,

Peng³

et al. 2011

Med Chem Res

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A series of chalcones derivatives were synthesized and evaluated for cytotoxic and antibacterial activities in vitro. These modifications changed their bioactivity profile and indicated a combination of SAR analysis toward the substituents in rings A and B of chalcones. Compounds 2, 6-8, 14-17, and 32 exhibited good cytotoxic properties against two human cancer cell lines HT29 and SGC7901. Compounds 16 and 17 showed high antibacterial activity toward 14 clinically isolated multidrugresistant strains. Subsequently, the structure of bi-bioactive compound 16 was determined using single-crystal X-ray diffraction. This study presents a few novel leading compounds for the development of potential antitumor and antibacterial agents.

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Antimicrobial and Antileishmanial Studies of Novel (2E)-3-(2-Chloro-6-methyl/methoxyquinolin-3-yl)-1-(Aryl)prop-2-en-1-ones

Cited by 22 publications

References 43 publications

Novel Halogenated Pyrazine-Based Chalcones as Potential Antimicrobial Drugs

Novel Halogenated Pyrazine-Based Chalcones as Potential Antimicrobial Drugs

In Vitro Activities of New 2-Substituted Quinolines against Leishmania donovani

Synthesis and crystal structure of chalcones as well as on cytotoxicity and antibacterial properties

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