- Bioactivity study of thiophene and pyrazole containing heterocycles
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Chalcones 3a-f were prepared by reacting thiophene containing pyrazolyl aldehyde (2) with different 2-hydroxy acetophenones 1a-f. The compounds 3a-f were transformed into different Pyrazolines 4a-f. The formation of chromene derivatives 5a-f occurred from the cyclization of 3a-f, which were then transformed into pyrazole derivatives 6a-f. Newly synthesized compounds have promising antibacterial activity against S. typhii and S. aureus, while weak activity against B. subtilis and E. coli. Compounds 5d and 6d had significant antifungal action towards A. niger, while most of the compounds were moderately active towards T. viride. Some of the synthesized compounds showed promising α-amylase inhibitory activity at 1 mg/mL concentration.
- Athare, Anil E.,Dare, Sushama B.,Kale, Nitin V.,Karale, Bhausaheb K.,Mhaske, Sadhana D.,Salve, Supriya P.,Takate, Sushama J.
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p. 891 - 899
(2021/09/08)
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- Synthesis and Antibacterial Screening of Some New Pyrazolylchromones and Pyrazolylcoumaran-3-ones
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Some new pyrazolylchromones 4a-e (flavone analogs) and pyrazolylcoumaran-3-ones 5a-e (aurone analogs) were synthesized by refluxing chalcones 3a-e in dimethyl sulfoxide/I2 and Pyridine/ Hg(OAc)2, respectively. Spectral techniques such as infrared, proton nuclear magnetic resonance, and mass spectrometry were used to confirm the structures of newly synthesized compounds. These compounds were studied for their antibacterial activities toward Bacillus subtilis, Staphylococcus aureus, Escherichia coli, and Salmonella typhi. Some of these compounds showed promising activity against test organisms.
- Takate, Sushama J.,Salve, Supriya P.,Dare, Sushama B.,Karale, Bhausaheb K.,Akolkar, Hemantkumar N.,Falke, Dnyaneshwar B.,Ghungurde, Rahul B.,Mhaske, Sadhana D.
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p. 525 - 530
(2021/02/02)
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- Iridium-Catalyzed C(sp3)?H Addition of Methyl Ethers across Intramolecular Carbon–Carbon Double Bonds Giving 2,3-Dihydrobenzofurans
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Intramolecular addition of an O-methyl C(sp3)?H bond across a carbon-carbon double bond occurs in the iridium-catalyzed reaction of methyl 2-(propen-2-yl)phenyl ethers. The Ir/(S)-DTBM-SEGPHOS catalyst promotes the reaction efficiently in toluene at 110–135 °C to afford 3,3-dimethyl-2,3-dihydrobenzofurans. Enantioselective C(sp3)?H addition is achieved in the reaction of methyl 2-(1-siloxyethenyl)phenyl ethers, affording enantioenriched 3-hydroxy-2,3-dihydrobenzofuran derivatives with up to 96% ee. (Figure presented.).
- Ohmura, Toshimichi,Kusaka, Satoshi,Torigoe, Takeru,Suginome, Michinori
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supporting information
p. 4448 - 4453
(2019/09/16)
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- Ultrasound-assisted synthesis and antimicrobial activity of tetrazole-based pyrazole and pyrimidine derivatives
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New tetrazole-based pyrazole and pyrimidine derivatives were synthesized by an ultrasound irradiation method. All compounds were characterized by infrared spectroscopy (IR), 1H nuclear magnetic resonance (NMR), 13C NMR, mass spectrometry (MS) and elemental analysis and assessed in vitro for their efficacy as antimicrobial agents against four bacteria (Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Pseudomonas aeruginosa) and two fungi (Candida albicans, Aspergillus Niger). Compounds 8a, 8e, 9a, 9b and 9e show potent activity against the tested strains compared to the reference drugs chloramphenicol and clotrimazole.
- Dofe, Vidya S.,Sarkate, Aniket P.,Shaikh, Zarina M.,Gill, Charansingh H.
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- One-pot two-step synthesis of 3-iodo-4-aryloxy coumarins and their Pd/C-catalyzed annulation to coumestans
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An efficient protocol for the synthesis of various coumestans from the intramolecular annulation of 3-iodo-4-aryloxy coumarins through C-H activation has been developed. When 3-iodo-4-aryloxy coumarins were treated with 10% Pd/C (0.3 mol% Pd) in the presence of sodium acetate, the corresponding coumestans were produced in good to excellent yield. Reusability of the palladium catalyst was investigated in up to three consecutive cycles and it was found that the yield of the reaction was almost unaltered. Sequential iodination and O-arylation of 4-hydroxy coumarins leading to the 3-iodo-4-aryloxy coumarins were also achieved in a one-pot two-step process starting from aryl iodides in high yield. Pivalic acid was revealed to be the most effective additive for the later method to produce 3-iodo-4-phenoxy coumarins. Different functional groups bearing electron-donating as well as withdrawing groups are also tolerant to the reaction conditions.
- Panda, Niranjan,Mattan, Irshad
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p. 7716 - 7725
(2018/03/01)
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- Synthesis, antimicrobial activity and anti-biofilm activity of novel tetrazole derivatives
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In the development of antimicrobial agents, we designed and synthesized novel tetrazole derivatives. The structures of compounds 6a-f and 7a-f were characterized by IR, 1H NMR, 13C NMR, MS and elemental analysis. These compounds were tested for their antimicrobial activity against a series of strains Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Pseudomonas aeruginosa and for antifungal activity against the strains Candida albicans, Candida glabrata, and Candida tropicalis. Compounds 6e, 6f, 7a, and 7f exhibit potent antimicrobial activities compared to the reference drugs streptomycin and miconazole. Tetrazole derivatives 7a-f also inhibit biofilm formation and compound 7f exhibits best anti-biofilm activity with a biofilm inhibitory concentration (BIC) as low as 0.9 μm.
- Dofe, Vidya S.,Sarkate, Aniket P.,Kathwate, Santosh H.,Gill, Charansingh H.
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p. 325 - 330
(2017/08/18)
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- synthesis of some 4-methyl-2-(3-methylbenzofuran-2- yl)quinoline -3-carboxylic acids
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In the present investigation, one-pot synthetic route for the synthesis of 4-methyl-2-(3- methylbenzofuran-2-yl)quinoline-3-carboxylic acids 3a-f has been described, involving the reaction of ethyl 2- (chloromethyl)-4-methylquinoline-3-carboxylate (1) with various 1-(2-hydroxyphenyl)ethanones 2a-f in refluxing MeCN with the presence of K2 CO3 as base and PEG-400 as phase transfer catalyst. The structures of all the newly- 2 3 synthesized compounds were confirmed by IR, 1H NMR, 13C NMR and HRMS.
- Fu, Xin B.,Li, Yang,Gao, Wen T.
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- 2,2,6,6-Tetramethylpiperidine-catalyzed, ortho-selective chlorination of phenols by sulfuryl chloride
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2,2,6,6-Tetramethylpiperidine (TMP)-catalyzed (1- 10%) chlorinations of phenols by SO2Cl2 in aromatic solvents are more ortho selective than with primary and less hindered secondary amine catalysts. Ortho-selective chlorination is successful even with electron deficient phenols such as 2-hydroxybenzaldehyde and 2'- hydroxyacetophenone. Notably, ortho selectivity increases with the reaction temperature. On the other hand, tetraalkylammonium chloride-catalyzed chlorinations are moderately para selective.
- Saper, Noam I.,Snider, Barry B.
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p. 809 - 813
(2014/04/03)
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- Use of transesterified 1,3-diketoesters in the synthesis of trisubstituted pyrazoles and their biological screening
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Starting from 2-acetylbenzofuran derivatives 1a-d, methyl/ethyl 4-substituted/unsubstituted benzofuran-2-yl)-2,4-dioxobutanoate 2a-d and 3a-d have been synthesized by Claisen's condensation reaction with diethyloxalate. The transesterified product, 1,3-diketoester 2a-d on condensation with phenyl hydrazine undergo cyclization to afford the corresponding methyl 5-(substituted/unsubstituted benzofuran-2-yl)-1-phenyl- 1H-pyrazole-3- carboxylate 4a-d, which upon further condensation with hydrazine hydrate yielded 5- (substituted/unsubstituted benzofuran-2-yl)-1-phenyl-1H-pyrazole-3- carbohydrazide 5a-d. The structures of the newly synthesized compounds 2a-d, 3a-d, 4a-d and 5a-d were characterized by their elemental analysis and spectral studies such as IR, 1H NMR, 13C NMR and MS. All the synthesized compounds were screened for their antimicrobial activity. Most of the synthesized compounds showed high sensitivity against the selected bacteria and fungi at various concentrations.
- Siddiqui, Naqui-Jahan,Idrees, Mohammad,Khati, Niraj T.,Dhonde, Madhukar G.
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- Synthesis and antibacterial studies of chloro-substituted 1,3-thiazines
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Thiazines are very useful units in the fields of medicinal and pharmaceutical chemistry and have been reported to exhibit a variety of biological activities. This has directed us to synthesize chloro-substituted thiazines from 2'-hydroxy-3',5'-dichloro-4-
- Rajput, P. R.,Gajbhiye, A. V.,Bhade, M. W.
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p. 5699 - 5701,3
(2020/09/15)
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- Cu-Mn spinel oxide catalyzed regioselective halogenation of phenols and N-heteroarenes
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A novel simple, mild chemo- and regioselective method has been developed for the halogenation of phenols using Cu-Mn spinel oxide as a catalyst and N-halosuccinimide as halogenating agent. In the presence of Cu-Mn spinel oxide B, both electron-withdrawing and electron-donating groups bearing phenols gave monohalogenated products in good to excellent yields with highest para-selectivity. The para-substituted phenol gave monohalogenated product with good yield and ortho-selectivity. N-Heteroarenes such as indoles and imidazoles also gave monohalogenated products with high selectivity. Unlike the copper-catalyzed halogenation, the present method works well with electron-withdrawing group bearing phenols and gives comparatively better yields and selectivity. The Cu-Mn spinel catalyst is robust and reused three times under optimized conditions without any loss in catalytic activity. Nonphenolics did not undergo this transformation.
- Singh, Parvinder Pal,Thatikonda, Thanusha,Kumar, K. A. Aravinda,Sawant, Sanghapal D.,Singh, Baldev,Sharma, Amit Kumar,Sharma,Singh, Deepika,Vishwakarma, Ram A.
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scheme or table
p. 5823 - 5828
(2012/09/05)
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- Synthesis of 3-(3-alkyl-5-thioxo-1H-4,5-dihydro-1,2,4-triazol-4-yl) aminocarbonylchromones
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A series of 3-(3-alkyl-5-thioxo-1H-4,5-dihydro-1,2,4-triazol-4-yl) aminocarbonylchromones has been prepared by oxidation of 3-formylchromone with Jones' reagent followed by reaction with 3-alkyl-4-amino-4,5-dihydro-1,2,4- triazole-5(1H)-thione in the presence of POCl3. The structures of the compounds were confirmed by IR, LC-MS, and 1H NMR spectra and elemental analyses.
- Cao, Linghua,Zhang, Lin,Cui, Pengyuan
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p. 635 - 640
(2007/10/03)
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- Sodium perborate: A facile synthesis of 1,2-benzisoxazole 2- oxides
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An efficient and convenient methodology has been developed for the conversion of 2-hydroxy phenyl ketoxime to 1,2- benzisoxazole 2-oxide with sodium perborate (SPB) in glacial acetic acid under mild reaction conditions. Interestingly when the reaction was carried out under reflux condition deoximation was observed in quantitative yield.
- Jadhav, Vidyadhar K.,Deshmukh, Anjali P.,Wadagaonkar, Prakash P.,Salunkhe, Manikrao M.
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p. 1521 - 1527
(2007/10/03)
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- A facile synthetic method of herbicidal 2,-dihydro-3-methylene-2-substituted - phenyl-1hisoindol-1-one derivatives
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Herbicidal 2,3-dihydro-3-methylene-2-substitutedphenyl-1 H-isoindol-1-one derivatives 7 have been synthesized. They were prepared from the easily available phenol derivatives 1 in 5 steps in moderate yields.
- Kim, Jae Nyoung,Ryu, Eung K.
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- Treatment of animals with 2,6-bis(2-hydroxybenzyl)phenols to eradicate trematodes
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A process for killing internal parasites of warm blooded animals which process comprises treating the infected animal with an effective amount of a composition comprising as active ingredient a compound of the general formula I: STR1 wherein R1
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- Substituted alkylaryl ketones and methods of use as herbicides
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Ring and side chain substituted alkylaryl ketones are useful in controlling the growth of germinating and seedling weed grasses and germinating and seedling broadleaf weeds.
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