Recent advances in the chemistry of 2-chloroquinoline-3-carbaldehyde and related analogs

Hamama, Wafaa S.; Ibrahim, Mona E.; Gooda, Ayaa A.; Zoorob, Hanafi H.

doi:10.1039/c7ra11537g

Cited by 48 publications

(34 citation statements)

References 90 publications

(111 reference statements)

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“…1 HNMR spectra of compounds 3-10 showed the presence of the (NH) proton and azomethine (CH═N) proton signals at the expected regions. 1 HNMR spectra of compounds 3-10 Showed singlet signals at the ranges δ 13.3-11.2 ppm corresponding to NH protons and singlet signals at the ranges δ 9.0-8.49 ppm corresponding to the azomthine protons. Furthermore, derivatives 4, 5, and 12 showed singlet signals at the ranges δ 3.02-3.8 ppm due to methyl group protons.…”

Section: Resultsmentioning

confidence: 99%

“…IR spectra were recorded on a BRUKER Vector 22 Germany spectrometer (KBr). 1 H NMR spectra were recorded on (Bruker) 400 MHz spectrometer using TMS as an internal reference. The Electron Impact mass spectra were obtained at 70 eV using Shimadzu QP-2010 Plus mass spectrometer.…”

Section: Generalmentioning

confidence: 99%

“…The chemistry of quinoline derivatives has been of increasing interest due to their vast chemical reactivity, biological and pharmaceutical activities [1][2][3][4][5]. It has been reported that these derivatives possesses anti-tuberculosis [6,7], Antiplasmodial [4], Antibacterial [5], antihistamine [6], anticancer [11][12][13][14], anti-hypertensive [9], antifungal [10], antimalarial [11], anti-HIV [12] and antioxidant activities [13].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Characterization and Evaluation of Anti-inflammatory and Analgesic Activity of Some Novel Quinoline Based Thiazolidinone Heterocycles

et al. 2018

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not only essential for survival but also at the same time is one of the major causes of human mortality [25,26]. It's known that, non-steroidal anti-inflammatory drugs (NSAIDs) are used to treat a wide variety of illnesses and diseases, such as inflammation [24], cancers [25] and the peripheral and central nervous system diseases [26]. The anti-inflammatory effect of NSAIDs arises from their ability to inhibit both COX-1 and COX-2 isoforms of cyclooxygenase (COX) enzyme [27]. Literature survey revealed that some of the synthesized derivatives having quinoline ring or bearing thiazole ring have significant antiinflammatory and analgesic activity [31-33, 20, 21]. In the light of above mentioned facts and our interest in designing new biologically active molecules, our efforts were directed towards I N this paper we report the synthesis of some quinoline based thiazolidinone derivatives (13-22) in a three-step process. Condensation of 2-hydrazinylquinoline 2 with different aromatic aldehydes gave the corresponding Schiff bases 3-10 which in turn were reacted with thioglycolic acid to furnish the corresponding thiazolidinone derivatives 13-20. Reaction of compound 2 with isatin or methyl isatin gave 1-sustituted-3-(2-(quinolin-2-yl)hydrazono) indolin-2-ones 11 and 12, which were converted to 1-substituted 3'-(quinolin-2-ylamino) spiro[indoline-3,2'-thiazolidine]-2,4'-dione 21 and 22 by cyclocondensation with thioglycolic acid. All newly synthesized compounds have been characterized by means of elemental analyses, IR, 1 H NMR and MS. Furthermore, all new thiazolidinone derivatives were evaluated for their anti-inflammatory and analgesic activity. The Study results revealed that the highest anti-inflammatory potency was gained by 6 derivatives according to the following order 22 > 17 >13 > 14 > 21 > 15, showing a good edema inhibition compared to the reference drug indomethacin. Compound 22 carrying indole ring system inhibited the edema volume significantly at the 1 st h post administration, and the activity was enhanced up to the 4 th h giving a promising edema volume inhibition compared to that produced by indomethacin. The longest duration of analgesic action up to 90 min post compounds administration was obtained by the compounds 13, 17 and 22, they exhibited potent analgesia compared to that obtained by aspirin.

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Section: Resultsmentioning

confidence: 99%

Section: Generalmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis, Characterization and Evaluation of Anti-inflammatory and Analgesic Activity of Some Novel Quinoline Based Thiazolidinone Heterocycles

et al. 2018

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“…It can be found in a variety of synthetic and natural antifungal drugs such as sitafloxacin and ciprofloxacin ( Figure ), suggesting the preference of nature for this scaffold and identifying it as one of medicinal chemistry's privileged structures. Specially, 2‐chloroquinoline based molecules are well‐known to exhibit various biological properties such as antimicrobial, anticancer, antifungal, antitubercular, DNA binding and photonuclease activity …”

Section: Introductionmentioning

confidence: 99%

“…It can be found in a variety of synthetic and natural antifungal drugs such as sitafloxacin and ciprofloxacin (Figure 2), suggesting the preference of nature for this scaffold and identifying it as one of medicinal chemistry's privileged structures. Specially, 2-chloroquinoline based molecules [34] are well-known to exhibit various biological properties such as antimicrobial, [35,36] anticancer, [37] antifungal, [38] antitubercular, [39] DNA binding and photonuclease activity. [40] Under this context and as a part of our ongoing research in the synthesis and biological evaluation of monocarbonyl curcumin analogs, [41][42][43] we would like to report herein the synthesis of 2-chloroquinolene based monocarbonyl curcumin analogs and their in vitro fungicidal and antioxidant activities.…”

Section: Introductionmentioning

confidence: 99%

Quinoline Based Monocarbonyl Curcumin Analogs as Potential Antifungal and Antioxidant Agents: Synthesis, Bioevaluation and Molecular Docking Study

Nagargoje

Akolkar

Siddiqui

et al. 2020

Chemistry & Biodiversity

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In search for new fungicidal and free radical scavenging agents, we synthesized a focused library of 2‐chloroquinoline based monocarbonyl analogs of curcumin (MACs). The synthesized MACs were evaluated for in vitro antifungal and antioxidant activity. The antifungal activity was evaluated against five different fungal strains such as Candida albicans, Fusarium oxysporum, Aspergillus flavus, Aspergillus niger, and Cryptococcus neoformans, respectively. Most of the synthesized MACs displayed promising antifungal activity compared to the standard drug Miconazole. Furthermore, molecular docking study on a crucial fungal enzyme sterol 14α‐demethylase (CYP51) could provide insight into the plausible mechanism of antifungal activity. MACs were also screened for in vitro radical scavenging activity using butylated hydroxytoluene (BHT) as a standard. Almost all MACs exhibited better antioxidant activity compared to BHT.

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Rhodium‐Catalyzed Selective C−H Bond Functionalization of Quinolines

et al. 2020

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In the last two decades, rhodium-based catalysts have been used extensively for the sp 2 and sp 3 CÀ H bond activation/functionalization of various arenes, heteroarenes, and aliphatic compounds, respectively. For quinoline functionalization rhodium has been used significantly as compared to other transition metals such as cobalt, copper, ruthenium, palladium and iridium. In this Minireview the progress on rhodium-catalyzed selective functionalization of quinoline N-oxides and 8-methylquinolines via sp 2 and sp 3 CÀ H bond activation, respectively have been highlighted. The main focus is on reaction mechanism, substrate scope, and positional selectivity.

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Recent advances in the chemistry of 2-chloroquinoline-3-carbaldehyde and related analogs

Abstract: This review describes the recent publications reported on the chemistry of 2-chloroquinoline-3-carbaldehydes. Heterocyclic quinoline ring systems are binary and fused cycles.

Cited by 48 publications

References 90 publications

Synthesis, Characterization and Evaluation of Anti-inflammatory and Analgesic Activity of Some Novel Quinoline Based Thiazolidinone Heterocycles

Synthesis, Characterization and Evaluation of Anti-inflammatory and Analgesic Activity of Some Novel Quinoline Based Thiazolidinone Heterocycles

Quinoline Based Monocarbonyl Curcumin Analogs as Potential Antifungal and Antioxidant Agents: Synthesis, Bioevaluation and Molecular Docking Study

Rhodium‐Catalyzed Selective C−H Bond Functionalization of Quinolines

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