Design, synthesis and antimicrobial activities of novel 1,3,5-thiadiazine-2-thione derivatives containing a 1,3,4-thiadiazole group

A series of novel 1,3,5-thiadiazine-2-thione derivatives containing a 1,3,4-thiadiazole group was designed and synthesized. The structures of all the compounds were well characterized using 1H NMR, 13C NMR and high-resolution mass spectrometer, and further confirmed by the X-ray diffraction analysis of 8d. The antimicrobial activities of all the target compounds against Xanthomonas oryzae pv. oryzicola, X. oryzae pv. oryzae, Rhizoctonia solani and Fusarium graminearum were evaluated. The in vitro antimicrobial bioassays indicated that some title compounds exhibited noteworthy antimicrobial effects against the above strains. Notably, the compound N-(5-(ethylthio)-1,3,4-thiadiazol-2-yl)-2-(5-methyl-6-thioxo-1,3,5-thiadiazinan-3-yl)acetamide (8a) displayed obvious antibacterial effects against X. oryzae pv. oryzicola and X. oryzae pv. oryzae at 100 μg/mL with the inhibition rates of 30% and 56%, respectively, which was better than the commercial bactericide thiodiazole-copper. In addition, the anti-R. solani EC50 value of 8a was 33.70 μg/mL, which was more effective than that of the commercial fungicide hymexazol (67.10 μg/mL). It was found that the substitutes in the 1,3,5-thiadiazine-2-thione and the 1,3,4-thiadiazole rings played a vital role in the antimicrobial activities of the title compounds. More active title compounds against phytopathogenic microorganisms might be obtained via further structural modification.

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Design, Synthesis and Antibacterial Activity of Novel Pyrimidine-Containing 4H-Chromen-4-one Derivatives

10.21203/rs.3.rs-92183/v1 ◽

2020 ◽

Author(s):

Shijun Su ◽

Mei Chen ◽

Xuemei Tang ◽

Feng Peng ◽

Tingting Liu ◽

...

Keyword(s):

Antibacterial Activity ◽

Inhibitory Effect ◽

Xanthomonas Oryzae ◽

Design Synthesis ◽

H Nmr ◽

Half Maximal Effective Concentration ◽

Bacterial Cell Membrane ◽

Better Than ◽

C Nmr

Abstract A series of pyrimidine-containing 4H-chromen-4-one derivatives were designed and synthesized by combining bioactive substructures. All compounds were characterized using 1H NMR, 13C NMR, 19F NMR and HRMS. Preliminary biological activity results showed that most of title compounds displayed significant inhibitory activity against Xanthomonas axonopodis pv. Citri (Xac), Xanthomonas oryzae pv. oryzae (Xoo) and Ralstonia solanacearum (Rs). In particular, compound 4c demonstrated a good inhibitory effect against Xac and Xoo, with half-maximal effective concentration(EC50) values of 15.5 and 14.9 μg/mL respectively, and that of compound 4h showed the best antibacterial activity against Rs with an EC50 value of 14.7 μg/mL, These results were better than both bismerthiazol (BT, 51.7, 70.1 and 52.7 μg/mL, respectively) and thiodiazole copper (TC, 77.9, 95.8 and 72.1 μg/mL respectively). In vivo antibacterial activity results indicated that compound 4c displayed better curative(42.4%) and protective (49.2%) activities for reducing rice bacterial leaf blight than both BT (35.2, 39.1%) and TC (30.8, 27.3%). The mechanism of compound 4c against Xoo was analysed through scanning electron microscopy (SEM). Results showed that the compound destroied the bacterial cell membrane structure. These results indicated that pyrimidine-containing 4H-chromen-4-one derivatives are valuable in the research of new agrochemicals.

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Regio- and stereoselective synthesis of [1,3]thiazolo[3,2-b][1,2,4]triazol-7-ium salts via electrophilic heterocyclization of 3-S-propargylthio-4Н-1,2,4-triazoles and their antimicrobial activity

Heterocyclic Communications ◽

10.1515/hc-2016-0233 ◽

2017 ◽

Vol 23 (2) ◽

pp. 109-113 ◽

Cited By ~ 9

Author(s):

Mikhailo Slivka ◽

Nataliya Korol ◽

Valerij Pantyo ◽

Vjacheslav Baumer ◽

Vasil Lendel

Keyword(s):

Antimicrobial Activity ◽

Diffraction Analysis ◽

Stereoselective Synthesis ◽

Geometric Isomers ◽

X Ray Diffraction ◽

X Ray ◽

H Nmr ◽

Electrophilic Heterocyclization ◽

Better Than ◽

C Nmr

AbstractA procedure for the preparation of the title salts via regioselective halocyclization of 3-S-propargylthio-4Н-1,2,4-triazoles is reported. Stereoselectivity of electrophilic heterocyclization depends on the nature of the electrophilic reagent: bromination is better than iodobromination and iodination. The heterocyclization with tellurium tetrahalogenides leads to the formation of a mixture of geometric isomers of the salts. Their structure was confirmed by 1H NMR, 13C NMR, НМВС and single crystal X-ray diffraction analysis.

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Synthesis, Characterization and Antimicrobial Activity of a New Preservative, 6-O-Chitosan Ester of P-Hydroxybenzoic Acid

Advanced Materials Research ◽

10.4028/www.scientific.net/amr.189-193.1049 ◽

2011 ◽

Vol 189-193 ◽

pp. 1049-1055

Author(s):

Xi Rong Zhao

Keyword(s):

Antimicrobial Activity ◽

Water Solubility ◽

Antimicrobial Activities ◽

Amic Acid ◽

Amino Group ◽

Gram Positive Bacteria ◽

H Nmr ◽

Escherchia Coli ◽

Better Than ◽

C Nmr

A new chitosan ester derivative, chitosan p-hydroxybenzoate is synthesized, which is expected to have antimicrobial activity similar to parabens. The amino group of chitosan reacts well with acyl chloride to prepare a N-amic acid-chitosan. The amino group of chitosan must be protected before synthesizing a 6-O-chitosan ester. Phthalic anhydride is selected to react with chitosan to form N-phthalimide chitosan whose free amino group is protected. By six steps chitosan p-hydroxybenzoate is synthesized. FTIR,1H NMR and13C NMR spectra show that the ester bond is formed between p-hydroxybenzonic acid and chitosan. Water solubility of the ester is slightly better than that of heptyl p-hydroxybenzoate, and its solubility in alcohol is greatly improved. Chitosan p-hydroxybenzoate showes broader spectrum antimicrobial activities. It has strong antimicrobial effects against Gram-negative, Gram-positive bacteria and yeasts. The MICs of chitosan p-hydroxybenzoate for Staphylococcus aureus and Escherchia coli are 0.01% and 0.025%, respectively.

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Synthesis, structure and in vitro cytotoxicity testing of some 2-aroylbenzofuran-3-ols

Acta Crystallographica Section C Structural Chemistry ◽

10.1107/s2053229620011018 ◽

2020 ◽

Vol 76 (9) ◽

pp. 874-882

Author(s):

Nguyen Tien Cong ◽

Huynh Thi Xuan Trang ◽

Pham Duc Dung ◽

Tran Hoang Phuong ◽

Vu Quoc Trung ◽

...

Keyword(s):

Human Cancer ◽

In Vitro Cytotoxicity ◽

X Ray Diffraction ◽

Hep G2 ◽

Hep G2 Cells ◽

X Ray ◽

Human Cancer Cell Lines ◽

H Nmr ◽

C Nmr

Five 2-aroyl-5-bromobenzo[b]furan-3-ol compounds (two of which are new) and four new 2-aroyl-5-iodobenzo[b]furan-3-ol compounds were synthesized starting from salicylic acid. The compounds were characterized by mass spectrometry and 1H NMR and 13C NMR spectroscopy. Single-crystal X-ray diffraction studies of four compounds, namely, (5-bromo-3-hydroxybenzofuran-2-yl)(4-fluorophenyl)methanone, C15H8BrFO3, (5-bromo-3-hydroxybenzofuran-2-yl)(4-chlorophenyl)methanone, C15H8BrClO3, (5-bromo-3-hydroxybenzofuran-2-yl)(4-bromophenyl)methanone, C15H8Br2O3, and (4-bromophenyl)(3-hydroxy-5-iodobenzofuran-2-yl)methanone, C15H8BrIO3, were also carried out. The compounds were tested for their in vitro cytotoxicity on the four human cancer cell lines KB, Hep-G2, Lu-1 and MCF7. Six compounds show good inhibiting abilities on Hep-G2 cells, with IC50 values of 1.39–8.03 µM.

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Novel Fluorinated 7-Hydroxycoumarin Derivatives Containing an Oxime Ether Moiety: Design, Synthesis, Crystal Structure and Biological Evaluation

Molecules ◽

10.3390/molecules26020372 ◽

2021 ◽

Vol 26 (2) ◽

pp. 372

Author(s):

Qing-Qing Wang ◽

Shu-Guang Zhang ◽

Jian Jiao ◽

Peng Dai ◽

Wei-Hua Zhang

Keyword(s):

Antifungal Activity ◽

Positive Control ◽

Biological Evaluation ◽

Gibberella Zeae ◽

X Ray Diffraction ◽

Oxime Ether ◽

Design Synthesis ◽

Antifungal Activities ◽

Better Than

A series of fluorinated 7-hydroxycoumarin derivatives containing an oxime ether moiety have been designed, synthesized and evaluated for their antifungal activity. All the target compounds were determined by 1H-NMR, 13C-NMR, FTIR and HR-MS spectra. The single-crystal structures of compounds 4e, 4h, 5h and 6c were further confirmed using X-ray diffraction. The antifungal activities against Botrytis cinerea (B. cinerea), Alternariasolani (A. solani), Gibberella zeae (G. zeae), Rhizoctorzia solani (R. solani), Colletotrichum orbiculare (C. orbiculare) and Alternaria alternata (A. alternata) were evaluated in vitro. The preliminary bioassays showed that some of the designed compounds displayed the promising antifungal activities against the above tested fungi. Strikingly, the target compounds 5f and 6h exhibited outstanding antifungal activity against B. cinerea at 100 μg/mL, with the corresponding inhibition rates reached 90.1 and 85.0%, which were better than the positive control Osthole (83.6%) and Azoxystrobin (46.5%). The compound 5f was identified as the promising fungicide candidate against B. cinerea with the EC50 values of 5.75 μg/mL, which was obviously better than Osthole (33.20 μg/mL) and Azoxystrobin (64.95 μg/mL). Meanwhile, the compound 5f showed remarkable antifungal activities against R. solani with the EC50 values of 28.96 μg/mL, which was better than Osthole (67.18 μg/mL) and equivalent to Azoxystrobin (21.34 μg/mL). The results provide a significant foundation for the search of novel fluorinated 7-hydroxycoumarin derivatives with good antifungal activity.

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Design, Synthesis, and In Vitro Antimicrobial Evaluation of Fused Pyrano[3,2-e]tetrazolo[1,5-c]pyrimidines and Diazepines

ISRN Organic Chemistry ◽

10.1155/2013/635384 ◽

2013 ◽

Vol 2013 ◽

pp. 1-9 ◽

Cited By ~ 1

Author(s):

Sankari Kanakaraju ◽

P. Sagar Vijay Kumar ◽

Bethanamudi Prasanna ◽

G. V. P. Chandramouli

Keyword(s):

Carbon Disulfide ◽

Phenacyl Bromide ◽

Mass Spectral Data ◽

Design Synthesis ◽

Mass Spectral ◽

H Nmr ◽

Elemental Analyses ◽

Antimicrobial Evaluation ◽

C Nmr

A series of novel pyranochromene-containing tetrazoles fused with pyrimidinethiones, pyrimidines, and diazepines 3a–f, 4a–f, and 5a–f were synthesized by condensation of the corresponding tetrazoles 2a–f with carbon disulfide, benzaldehyde, and 4-methoxy phenacyl bromide, respectively. The compound 2a–f was obtained by reaction of pyrano[3,2-c]chromenes 1a–f with sodium azide. The structures of the newly synthesized compounds 2a–f to 5a–f were established on the basis of their elemental analyses, IR, 1H NMR, 13C NMR, and mass spectral data. All of the title compounds were subjected to in vitro antibacterial testing against four pathogenic strains and antifungal screening against two fungi. Preliminary results indicate that some of them exhibited promising activities and that they deserve more consideration as potential antimicrobials.

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Design, synthesis, and insecticidal activity of novel 1-alkoxy-2-nitroguanidines

RSC Advances ◽

10.1039/c7ra11454k ◽

2018 ◽

Vol 8 (4) ◽

pp. 1838-1845 ◽

Cited By ~ 1

Author(s):

Dongyan Yang ◽

Chuan Wan ◽

Yumei Xiao ◽

Chuanliang Che ◽

Changhui Rui ◽

...

Keyword(s):

High Resolution ◽

Insecticidal Activity ◽

X Ray Diffraction ◽

Design Synthesis ◽

X Ray ◽

H Nmr ◽

Lead Compounds ◽

Alkoxy Groups ◽

C Nmr

In searching for new insecticidal lead compounds, a series of novel 1-alkoxy-2-nitroguanidine, guadipyr analogues bearing alkoxy groups were designed, synthesized and confirmed by 1H NMR, 13C NMR, high-resolution MS and X-ray diffraction.

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Synthesis, structure and in vitro cytotoxicity testing of some 1,3,4-oxadiazoline derivatives from 2-hydroxy-5-iodobenzoic acid

Acta Crystallographica Section C Structural Chemistry ◽

10.1107/s2053229618008719 ◽

2018 ◽

Vol 74 (7) ◽

pp. 839-846 ◽

Cited By ~ 2

Author(s):

Cong Nguyen Tien ◽

Thin Nguyen Van ◽

Giang Le Duc ◽

Manh Vu Quoc ◽

Trung Vu Quoc ◽

...

Keyword(s):

Human Cancer ◽

In Vitro Cytotoxicity ◽

X Ray Diffraction ◽

Hep G2 ◽

X Ray ◽

Human Cancer Cell Lines ◽

Π Interactions ◽

H Nmr ◽

C Nmr

The syntheses of nine new 5-iodosalicylic acid-based 1,3,4-oxadiazoline derivatives starting from methyl salicylate are described. These compounds are 2-[4-acetyl-5-methyl-5-(3-nitrophenyl)-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate (6a), 2-[4-acetyl-5-methyl-5-(4-nitrophenyl)-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate (6b), 2-(4-acetyl-5-methyl-5-phenyl-4,5-dihydro-1,3,4-oxadiazol-2-yl)-4-iodophenyl acetate, C19H17IN2O4 (6c), 2-[4-acetyl-5-(4-fluorophenyl)-5-methyl-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate, C19H16FIN2O4 (6d), 2-[4-acetyl-5-(4-chlorophenyl)-5-methyl-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate, C19H16ClIN2O4 (6e), 2-[4-acetyl-5-(3-bromophenyl)-5-methyl-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate (6f), 2-[4-acetyl-5-(4-bromophenyl)-5-methyl-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate (6g), 2-[4-acetyl-5-methyl-5-(4-methylphenyl)-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate (6h) and 2-[5-(4-acetamidophenyl)-4-acetyl-5-methyl-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate (6i). The compounds were characterized by mass, 1H NMR and 13C NMR spectroscopies. Single-crystal X-ray diffraction studies were also carried out for 6c, 6d and 6e. Compounds 6c and 6d are isomorphous, with the 1,3,4-oxadiazoline ring having an envelope conformation, where the disubstituted C atom is the flap. The packing is determined by C—H...O, C—H...π and I...π interactions. For 6e, the 1,3,4-oxadiazoline ring is almost planar. In the packing, Cl...π interactions are observed, while the I atom is not involved in short interactions. Compounds 6d, 6e, 6f and 6h show good inhibiting abilities on the human cancer cell lines KB and Hep-G2, with IC50 values of 0.9–4.5 µM.

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SYNTHESIS AND STRUCTURAL ELUCIDATION OF AMINO ACETYLENIC AND THIOCARBAMATES DERIVATIVES FOR 2-MERCAPTOBENZOTHIAZOLE AS ANTIMICROBIAL AGENTS

International Journal of Pharmacy and Pharmaceutical Sciences ◽

10.22159/ijpps.2017v9i2.15760 ◽

2017 ◽

Vol 9 (2) ◽

pp. 192

Author(s):

Aseel Alsarahni ◽

Zuhair Muhi Eldeen ◽

Elham Al-kaissi ◽

Ibrahim Al- Adham ◽

Najah Al-muhtaseb

Keyword(s):

Antimicrobial Activity ◽

Elemental Analysis ◽

Antimicrobial Agents ◽

Diffusion Method ◽

Benzothiazole Derivatives ◽

H Nmr ◽

Ft Ir ◽

Potential Antimicrobial Activity ◽

C Nmr

Objective: To design and synthesize amino acetylenic and thiocarbonate of 2-mercapto-1,3-benthiazoles as potential antimicrobial agents.Methods: A new series of 2-{[4-(t-amino-1-yl) but-2-yn-1-yl] sulfanyl}-1,3-benzothiazole derivatives (AZ1-AZ6), and S-1,3-benzothiazol-2-yl-O-alkyl carbonothioate derivatives were synthesised, with the aim that the target compounds show new and potential antimicrobial activity. The elemental analysis was indicated by the EuroEA elemental analyzer, and biological characterization was via IR, 1H-NMR, [13]C-NMR, DSC were determined with the aid of Bruker FT-IR and Varian 300 MHz spectrometer using DMSO-d6 as a solvent. In vitro antimicrobial activity, evaluation was done for the synthesised compounds, by agar diffusion method and broth dilution test. The minimum inhibitory concentration (MIC) and the minimum bactericidal concentration (MBC) were determined. Results: The IR, 1H-NMR, 13C-NMR, DSC and elemental analysis were consistent with the assigned structures. Compound of 2-{[4-(4-methylpiperazin-1-yl)but-2-yn-1-yl] sulfanyl}-1,3-benzothiazole (AZ1), 2-{[4-(2-methylpiperidin-1-yl)but-2-yn-1-yl]sulfanyl}-1,3-benzothiazole (AZ2), 2-{[4-(piperidin-1-yl) but-2-yn-1-yl]sulfanyl}-1, 3-benzothiazole (AZ6), S-1,3-benzothiazol-2-yl-O-ethyl carbonothioate (AZ7), and S-1,3-benzothiazol-2-yl-O-(2-methylpropyl) carbonothioate (AZ9) showed the highest antimicrobial activity against Pseudomonas aeruginosa (P. aeruginosa), AZ-9 demonstrated the highest antifungal activity against Candida albicans (C. albicans), with MIC of 31.25 µg/ml.Conclusion: These promising results promoted our interest to investigate other structural analogues for their antimicrobial activity further.

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A series of Mn(i) photo-activated carbon monoxide-releasing molecules with benzimidazole coligands: synthesis, structural characterization, CO releasing properties and biological activity evaluation

RSC Advances ◽

10.1039/c9ra01370a ◽

2019 ◽

Vol 9 (36) ◽

pp. 20505-20512 ◽

Cited By ~ 1

Author(s):

Mixia Hu ◽

YaLi Yan ◽

Baohua Zhu ◽

Fei Chang ◽

Shiyong Yu ◽

...

Keyword(s):

Carbon Monoxide ◽

Biological Activity ◽

Activated Carbon ◽

Fluorescence Spectroscopy ◽

Single Crystal ◽

Structural Characterization ◽

X Ray Diffraction ◽

X Ray ◽

H Nmr ◽

C Nmr

Five Mn(i) photo-activated carbon monoxide-releasing molecules were synthesized by reactions of MnBr(CO)5 with L1–L4, and characterized via single crystal X-ray diffraction, 1H-NMR, 13C-NMR, IR, UV-vis and fluorescence spectroscopy.

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