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

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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Design, Synthesis, and Biological Activity of Novel Myricetin Derivatives Containing Amide, Thioether, and 1,3,4-Thiadiazole Moieties

Molecules ◽

10.3390/molecules23123132 ◽

2018 ◽

Vol 23 (12) ◽

pp. 3132 ◽

Cited By ~ 5

Author(s):

Xianghui Ruan ◽

Cheng Zhang ◽

Shichun Jiang ◽

Tao Guo ◽

Rongjiao Xia ◽

...

Keyword(s):

Antibacterial Activity ◽

Pathogenic Bacteria ◽

Antibacterial Activities ◽

Xanthomonas Oryzae ◽

Design Synthesis ◽

Antiviral Activities ◽

Potential Alternative ◽

Better Than

A series of myricetin derivatives containing amide, thioether, and 1,3,4-thiadiazole moieties were designed and synthesized, and their antiviral and antibacterial activities were assessed. The bioassays showed that all the title compounds exhibited potent in vitro antibacterial activities against Xanthomonas citri (Xac), Ralstonia solanacearum (Rs), and Xanthomonas oryzae pv. Oryzae (Xoo). In particular, the compounds 5a, 5f, 5g, 5h, 5i, and 5l, with EC50 values of 11.5–27.3 μg/mL, showed potent antibacterial activity against Xac that was better than the commercial bactericides Bismerthiazol (34.7 μg/mL) and Thiodiazole copper (41.1% μg/mL). Moreover, the in vivo antiviral activities against tobacco mosaic virus (TMV) of the target compounds were also tested. Among these compounds, the curative, protection, and inactivation activities of 5g were 49.9, 52.9, and 73.3%, respectively, which were better than that of the commercial antiviral Ribavirin (40.6, 51.1, and 71.1%, respectively). This study demonstrates that myricetin derivatives bearing amide, thioether, and 1,3,4-thiadiazole moieties can serve as potential alternative templates for the development of novel, highly efficient inhibitors against plant pathogenic bacteria and viruses.

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Design, synthesis, and antibacterial activity of novel myricetin derivatives containing sulfonate

Monatshefte für Chemie - Chemical Monthly ◽

10.1007/s00706-021-02739-1 ◽

2021 ◽

Vol 152 (3) ◽

pp. 345-356

Author(s):

Shijun Su ◽

Qing Zhou ◽

Xuemei Tang ◽

Feng Peng ◽

Tingting Liu ◽

...

Keyword(s):

Antibacterial Activity ◽

Biological Activities ◽

Xanthomonas Oryzae ◽

Antibacterial Mechanism ◽

Design Synthesis ◽

Xanthomonas Axonopodis ◽

Scanning Electron ◽

Better Than

AbstractA series of myricetin derivatives containing sulfonate groups were designed and synthesized. Preliminary antibacterial activity showed that most of the target compounds exhibited significant biological activities against Xanthomonas axonopodis pv. Citri (Xac), Ralstonia solanacearum (Rs), and Xanthomonas oryzae pv. Oryzae (Xoo). In particular, the EC50 value of compound 3e was 13.76 μg/cm3 against Xac, which was better than commercial reagents bismerthiazol (50.32 µg/cm3) and thiodiazole copper. (83.27 µg/cm3), and the EC50 value of compound 3j was 11.92 μg/cm3 against Xoo in vitro, The result was better than that of bismerthiazol (72.08 µg/cm3) and thiodiazole copper (99.26 µg/cm3). Compound 3j displayed the better in vivo activity against rice bacterial leaf blight than bismerthiazol and thiodiazole copper. Meanwhile, the antibacterial mechanism of compounds 3e and 3j was studied by scanning electron microscope (SEM). These results suggested that myricetin derivatives containing sulfonate can be considered as a new antibacterial reagents. Graphic abstract

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Synthesis and Antibacterial Evaluation of Novel 1,3,4-Oxadiazole Derivatives Containing Sulfonate/Carboxylate Moiety

Molecules ◽

10.3390/molecules25071488 ◽

2020 ◽

Vol 25 (7) ◽

pp. 1488

Author(s):

Lei Wang ◽

Xia Zhou ◽

Hui Lu ◽

Xianfu Mu ◽

Linhong Jin

Keyword(s):

Antibacterial Activity ◽

Inhibitory Effect ◽

Sem Analysis ◽

Leaf Blight ◽

Xanthomonas Oryzae ◽

Bacterial Leaf Blight ◽

Xanthomonas Axonopodis ◽

Better Than

In order to discover new lead compounds with high antibacterial activity, a series of new derivatives were designed and synthesized by introducing a sulfonate or carboxylate moiety into the 1,3,4-oxadiazole structure. Antibacterial activity against two phytopathogens, Xanthomonas oryzae pv. oryzae (Xoo) and Xanthomonas axonopodis pv. citri (Xac), was assayed in vitro. The preliminary results indicated that ten compounds including 4a-1-4a-4 and 4a-11-4a-16 had good antibacterial activity against Xoo, with EC50 values ranging from 50.1-112.5 µM, which was better than those of Bismerthiazol (253.5 µM) and Thiodiazole copper (467.4 µM). Meanwhile, 4a-1, 4a-2, 4a-3 and 4a-4 demonstrated good inhibitory effect against Xanthomonas axonopodis pv. citri with EC50 values around 95.8-155.2 µM which were better than those of bismerthiazol (274.3 µM) and thiodiazole copper (406.3 µM). In addition, in vivo protection activity of compound 4a-2 and 4a-3 against rice bacterial leaf blight was 68.6% and 62.3%, respectively, which were better than bismerthiazol (49.6%) and thiodiazole copper (42.2%). Curative activity of compound 4a-2 and 4a-3 against rice bacterial leaf blight was 62.3% and 56.0%, which were better than bismerthiazol (42.9%) and thiodiazole copper (36.1%). Through scanning electron microscopy (SEM) analysis, it was observed that compound 4a-2 caused the cell membrane of Xanthomonas oryzae pv. oryzae ruptured or deformed. The present results indicated novel derivatives of 5-phenyl sulfonate methyl 1,3,4-oxadiazole might be potential antibacterial agents.

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

PeerJ ◽

10.7717/peerj.7581 ◽

2019 ◽

Vol 7 ◽

pp. e7581 ◽

Cited By ~ 1

Author(s):

Jinghua Yan ◽

Weijie Si ◽

Haoran Hu ◽

Xu Zhao ◽

Min Chen ◽

...

Keyword(s):

Antimicrobial Activities ◽

Vital Role ◽

X Ray Diffraction ◽

Design Synthesis ◽

H Nmr ◽

Phytopathogenic Microorganisms ◽

High Resolution Mass Spectrometer ◽

Better Than ◽

C Nmr

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 evaluation of ocotillol derivatives with polycyclic nitrogen-containing groups

Future Medicinal Chemistry ◽

10.4155/fmc-2020-0364 ◽

2021 ◽

Author(s):

Yucheng Cao ◽

Kaiyi Wang ◽

Jiali Wang ◽

Haoran Cheng ◽

Mengxin Ma ◽

...

Keyword(s):

Antibacterial Activity ◽

Multidrug Resistant ◽

Inhibitory Effect ◽

Resistant Bacteria ◽

Design Synthesis ◽

In Vitro Antibacterial Activity ◽

Strong Inhibitory Effect ◽

Hospital Acquired ◽

Derivatives Of

Aim: With the increasing abuse of antibacterial drugs, multidrug-resistant bacteria have become a burden on human health and the healthcare system. To find alternative compounds effective against hospital-acquired methicillin-resistant Staphylococcus aureus (HA-MRSA), novel derivatives of ocotillol were synthesized. Methods & Results: Ocotillol derivatives with polycyclic nitrogen-containing groups were synthesized and evaluated for in vitro antibacterial activity. Compounds 36–39 exhibited potent antibacterial activity against hospital-acquired MRSA, with MIC = 8–64 μg/ml. Additionally, a combination of compound 37 and the commercially available antibiotic kanamycin showed synergistic inhibitory effects, with a fractional inhibitory concentration index of ≤0.375. Conclusion: Compound 37 has a strong inhibitory effect, and this derivative has potential for use as a pharmacological tool to explore antibacterial mechanisms.

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Design, Synthesis, and Molecular Docking of 1-(1-(4-Chlorophenyl)-2-(phenylsulfonyl)ethylidene)-2-phenylhydrazine as Potent Nonazole Anticandidal Agent

Journal of Chemistry ◽

10.1155/2014/154357 ◽

2014 ◽

Vol 2014 ◽

pp. 1-8 ◽

Cited By ~ 8

Author(s):

Hazem A. Ghabbour ◽

Maha M. Qabeel ◽

Wagdy M. Eldehna ◽

Abdullah Al-Dhfyan ◽

Hatem A. Abdel-Aziz

Keyword(s):

Human Breast ◽

Binding Interaction ◽

Design Synthesis ◽

Standard Drug ◽

H Nmr ◽

Normal Human Breast ◽

Normal Human ◽

Human Breast Cell Line ◽

Human Breast Cell ◽

C Nmr

1-(1-(4-Chlorophenyl)-2-(phenylsulfonyl)ethylidene)-2-phenylhydrazine (13) was designed and synthesized as potential nonazole anticandidal agent and precisely characterized by IR,1H NMR,13C NMR, and ESI-MS. The anti-Candidaactivity of13was evaluated against fourCandidaspecies (C. albicans, C. krusei, C. parapsilosis, andC. glabrata). Compound13displayed good anticandidal activities (MIC=0.39, 0.195, 0.39, and 1.56 μmol/mL, resp.) in comparison with that of the standard drug fluconazole (MIC=0.195, inactive, 1.56, and 1.56 μmol/mL, resp.) againstC. albicans, C. krusei, C. parapsilosis, andC. glabrata, respectively. A molecular modeling of the newly synthesized compound13was built in order to investigate its mode of action towards the prospective target cytochrome P450-dependent enzyme lanosterol 14α-demethylase (PDB-code: 1EA1). The docking results showed a similar binding interaction of13and fluconazole at the active site of CYT P450 14α-sterol demethylase. Furthermore, compound13showed no cytotoxicity against normal human breast cell line MCF10A.

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Cationic copolymerization of 1,3-pentadiene with α-pinene

Journal of Polymer Engineering ◽

10.1515/polyeng-2014-0062 ◽

2014 ◽

Vol 34 (7) ◽

pp. 583-589 ◽

Cited By ~ 1

Author(s):

Ai-Yuan Li ◽

Xiang-Dong Sun ◽

Hui-Bo Zhang ◽

Yong-Chun Zhang ◽

Bin Wang ◽

...

Keyword(s):

Average Molecular Weight ◽

Gel Permeation Chromatography ◽

Polymerization Temperature ◽

Scanning Calorimetry ◽

Gardner Color ◽

H Nmr ◽

Cationic Copolymerization ◽

Ft Ir ◽

Better Than ◽

C Nmr

Abstract The cationic copolymerization of 1,3-pentadiene (PD) with α-pinene (AP) initiated by aluminum trichloride (AlCl3) was carried out in N-pentane solvent. The effects of the polymerization temperature and the comonomer composition on the yield of the copolymer, softening point, Gardner color scale and number-average molecular weight (Mn) are discussed. The performance of the copolymer was better than that of AP homopolymer (PAP) and PD homopolymer (PPD). The structure of the copolymer was characterized by Fourier transform infrared spectroscopy (FT-IR), 1H-nuclear magnetic resonance (1H-NMR), 13C-NMR, differential scanning calorimetry (DSC) and gel permeation chromatography (GPC). In addition, the reactivity ratios for AP (M1) and PD (M2) determined by the Kelen-Tudos method from low-conversion data are r1=0.58 and r2=5.92, respectively.

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TRANSFORMATION OF ETHYL-P-METHOXYCINNAMATE TO P –METHOXYCINNAMIC ACID FROM KENCUR (Kaempheria galanga L.) AND THEIR ANTIBACTERIAL ACTIVITY

ALCHEMY Jurnal Penelitian Kimia ◽

10.20961/alchemy.13.2.8472.176-190 ◽

2017 ◽

Vol 13 (2) ◽

pp. 176

Author(s):

Muhamad Salman Fareza ◽

Rehana Rehana ◽

Nuryanti Nuryanti ◽

Didin Mujahidin

Keyword(s):

Antibacterial Activity ◽

Antibacterial Properties ◽

Separation And Purification ◽

E Coli ◽

H Nmr ◽

Alkaline Conditions ◽

Methoxycinnamic Acid ◽

Vacuum Liquid Chromatography ◽

Hydrolysis Of ◽

C Nmr

This study aimed to evaluate the antibacterial properties of ethyl-p-methoxycinnamate and p-methoxycinnamate acid from Kaempheria galanga L. Ethyl-p-methoxycinnamate was isolated from the n-hexane rhizome extract of Kaempheria galanga L. Separation and purification of this compound was carried out with vacuum liquid chromatography and column chromatography. Hydrolysis of ethyl-p-methoxycinnamic under alkaline conditions obtained p-methoxycinnamic acid with a good yield of 85 %. The structure of the compounds were charactrized with IR, NMR spectrophotometer (1H-NMR and 13C-NMR) and mass spectrophotometer. The antibacterial properties of the compounds were evaluated using microdilution methods against B. cereus ATCC 11778, L. monocytogenes ATCC 7644, E. coli ATCC 25922, S. enterica sv Typhimurium ATCC 14028, and E. aerogenes ATCC 13048. The compounds showed weak antibacterial properties. Only ethyl p-methoxycinnamate showed the strongest antibacterial activity, especially against B. cereus ATCC 11778 bacteria with MIC values of 62.5 mg /mL. The change of the functional groups provided no significant impact on the antibacterial activity.

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The PAX3 and 7 homeodomains have evolved unique determinants that influence DNA-binding, structure and communication with the paired domain

10.1101/701656 ◽

2019 ◽

Author(s):

Gareth N. Corry ◽

Brian D. Sykes ◽

D. Alan Underhill

Keyword(s):

Dna Binding ◽

Protein Interactions ◽

Ternary Complex ◽

Phylogenetic Analyses ◽

Inhibitory Effect ◽

Binding Assays ◽

Paired Domain ◽

Functional Diversification ◽

H Nmr

ABSTRACTThe PAX (paired box) family is a collection of metazoan transcription factors defined by the paired domain, which confers sequence-specific DNA-binding. Ancestral PAX proteins also contained a homeodomain, which can communicate with the paired domain to modulate DNA-binding. In the present study, we sought to identify determinants of this functional interaction using the paralogous PAX3 and 7 proteins. First, we evaluated a group of heterologous paired domains and homeodomains for the ability to bind DNA cooperatively through formation of a ternary complex (paired domain:homeodomain:DNA). This revealed that capacity for ternary complex formation was unique to the PAX3 and 7 homeodomains and therefore not simply a consequence of DNA-binding. We also found PAX3 and 7 were distinguished by an extended region of conservation N-terminal to the homeodomain (NTE). Phylogenetic analyses established the NTE was restricted to PAX3/7 orthologs of segmented metazoans, indicating it arose in a bilaterian precursor prior to separation of deuterostomes and protostomes. In DNA-binding assays, presence of the NTE caused a decrease in monomeric binding by the PAX3 homeodomain that reflected a lack of secondary structure in 1D-1H-NMR. Nevertheless, this inhibitory effect could be overcome by homeodomain dimerization or cooperative binding with the paired domain, establishing that protein interactions could induce homeodomain folding in the presence of the NTE. Strikingly, the PAX7 counterpart did not impair homeodomain binding, revealing inherent differences that could account for its distinct target profile in vivo. Collectively, these findings identify critical determinants of PAX3 and 7 activity, which contribute to their functional diversification.

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Design, Synthesis, and Biological Activity of Novel penta-1,4-dien-3-one Derivatives Containing a H-phosphonate Scaffold

10.20944/preprints201812.0311.v1 ◽

2018 ◽

Author(s):

Lijuan Chen ◽

Tao Guo ◽

Rongjiao Xia ◽

Xu Tang ◽

Ying Chen ◽

...

Keyword(s):

31P Nmr ◽

Antiviral Agents ◽

Antibacterial Activities ◽

Effective Concentration ◽

Xanthomonas Oryzae ◽

Protective Activity ◽

Design Synthesis ◽

Xanthomonas Axonopodis ◽

Antiviral Activities ◽

Better Than

A series of penta-1,4-dien-3-one containing a H-phosphonate scaffold were designed and synthesized. The structures of all title compounds were determined by 1H-NMR, 13C-NMR, 31P-NMR, and HRMS. Bioassay results showed that several of the title compounds exhibited remarkable antibacterial and antiviral activities. Among these, compounds 3c and 3o exhibited substantial antibacterial activities against Xanthomonas oryzae pv. Oryzae (Xoo) and Xanthomonas axonopodis pv. citri (Xac). In addition, compounds 3c, 3f, and 3r showed remarkable curative activities against tobacco mosaic virus (TMV), with 50% effective concentration (EC50) values of 290.0, 234.0, and 373.6 μg/mL, respectively. These were superior to that of ningnanmycin (386.2 μg/mL). Compound 3r exhibited comparative protective activity against TMV, with an EC50 value of 291.1 μg/mL, which was better than that of ningnanmycin (297.1 μg/mL). Notably, the solubility of all title compounds improved relative to the lead compound curcumin. These results suggest that penta-1,4-dien-3-one containing a H-phosphonate scaffold may be considered as an activator for antibacterial and antiviral agents.

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