Synthesis and Fungicidal Activity of Novel N-Nitro-2-Pyrimidinamine Derivatives

2013 ◽  
Vol 634-638 ◽  
pp. 1184-1191
Author(s):  
Wen Yan Qu ◽  
Jian Zhao ◽  
Bei Bei Gao ◽  
Shuo Chen ◽  
Zhi Fu Jiang ◽  
...  
Keyword(s):  
Ethyl Acetoacetate ◽  
Fungicidal Activity ◽  
High Efficiency ◽  
Fungal Species ◽  
Dimethyl Malonate ◽  
Mycelium Growth ◽  
Structure Activity ◽  
Relationship Of

Two series of novel N-nitro-2-pyrimidinamine derivatives were synthesized from ethyl acetoacetate, dimethyl malonate and nitroguanidine with good yields and high efficiency. The fungicidal activities of the synthesized compounds against nine fungal species were studied both in vitro and in vivo. Some of these compounds like 4,6-dihydr oxy -N-nitro-2-pyrimidinamine and 4,6-dihydroxy-5-isopentyl-N-nitro-2-pyrimidinamine showed obvious inhibitory of the mycelium growth at 50 mg/L. The structure-activity relationship of these compounds was also discussed.

Discovery and Structure−Activity Relationship of Antagonists of B-Cell Lymphoma 2 Family Proteins with Chemopotentiation Activity in Vitro and in Vivo

2006 ◽  
Vol 49 (3) ◽  
pp. 1165-1181 ◽  
Author(s):  
Michael D. Wendt ◽  
Wang Shen ◽  
Aaron Kunzer ◽  
William J. McClellan ◽  
Milan Bruncko ◽  
...  
Keyword(s):  
B Cell ◽  
Cell Lymphoma ◽  
B Cell Lymphoma ◽  
Structure Activity Relationship ◽  
Activity Relationship ◽  
Structure Activity ◽  
Relationship Of

STEROID AND PHYTO-OESTROGEN BINDING TO SHEEP UTERINE RECEPTORS IN VITRO

1972 ◽  
Vol 52 (2) ◽  
pp. 299-310 ◽  
Author(s):  
D. A. SHUTT ◽  
R. I. COX
Keyword(s):  
Binding Sites ◽  
Biochanin A ◽  
Hydroxyl Group ◽  
Binding Affinities ◽  
Structure Activity ◽  
Biological Potency ◽  
Competitive Protein Binding ◽  
Relationship Of

SUMMARY The binding affinities and receptor specificity of sheep uterine cytosol for steroid oestrogens and also for weak plant oestrogens of the isoflavone and coumestan groups and some synthetic compounds were studied. The binding affinities of the weak oestrogens fall within a range which has usually been neglected. Relative molar binding (RMB) affinities for the steroid oestrogens confirmed the importance of the phenolic 3-hydroxyl group and the influence of substitutions at C-16 and C-17, as seen with uterine cytosols from other species. Relative molar binding affinities were very much lower when the oestrogens were present as sulphate esters, glucosiduronate and methyl ether derivatives; acetates showed similar RMB affinities to their parent compounds. Phyto-oestrogens were found to compete with oestradiol for binding sites. Coumestrol and miroestrol had the highest RMB affinities of about 5 (oestradiol-17β = 100) when incubated at 25 °C, and values for genistein, equol, daidzein and O-desmethylangolensin lay between 1 and 0·05. The mono-methoxy compounds, biochanin A, formononetin and 4′-methoxy-coumestrol had RMB affinities of less than 0·01. Incubation at 37, 25 and 4 °C showed that RMB affinities were greater at the lower temperatures. Relative molar binding affinities of the phyto-oestrogens in vitro compared with their oestrogenic potencies in vivo showed that the ranking of most of the compounds by these two criteria was similar. Structure-activity correlations were deduced from the results. A similar relationship of RMB affinity to biological potency was also noted for the steroid oestrogens and a homologous series of stilbenediols. The results obtained are relevant to competitive protein-binding analyses and to the mechanism of action of oestrogens and phyto-oestrogens.

scholarly journals Synthesis, Fungicidal Activity and SAR of 2-Thiazolamide/Pyrazolamide-Cyclohexylsulfonamides against Botrytis cinerea

Molecules ◽  
2019 ◽  
Vol 24 (14) ◽  
pp. 2607
Author(s):  
Zhang ◽  
Meng ◽  
Xie ◽  
Yang ◽  
Zhang ◽  
...  
Keyword(s):  
Fungicidal Activity ◽  
Condensation Reaction ◽  
Effective Concentration ◽  
Single Crystal Diffraction ◽  
X Ray ◽  
Structure Activity ◽  
Median Effective Concentration ◽  
Germination Experiment

In order to explore more efficient sulfonamides against Botrytis cinereal, 36 novel cyclohexylsulfonamides were synthesized by N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide (EDCI) and 1-hydroxybenzotriazole (HOBt) condensation reaction using chesulfamide as a lead compound, introducing thiazole and pyrazole active groups. Their structures were characterized by 1H-NMR, 13C-NMR, mass spectrum (MS), and elemental analysis. Compound III -31 was further confirmed by X-ray single crystal diffraction. The in vitro and in vivo fungicidal activities against B. cinerea were evaluated by three bioassay methods. The results of mycelial growth demonstrated that median effective concentration (EC50) values of nine compounds were close to boscalid (EC50 = 1.72 µg/mL) and procymidone (EC50 = 1.79 µg/mL) against B. cinerea (KZ-9). In the spore germination experiment, it was found that compounds III-19 and III-31 inhibited germination 93.89 and 98.00%, respectively; at 10 µg/mL, they approached boscalid (95.97%). In the tomato pot experiment, the control effects of two compounds (III-21 and III-27) were 89.80 and 87.90%, respectively, at 200 µg/mL which were significantly higher than boscalid (81.99%). The structure–activity relationship (SAR) was also discussed, which provided a valuable idea for developing new fungicides.

scholarly journals Antioxidant, Antifungal and Insecticidal Activity of Triterpenoids Spinasterol, 22,23-Dihydrospinasterol Isolated from Colocynthis (Citrullus colocynthis L.) Leaves.

2020 ◽  
Author(s):  
Maqsood Ahmed ◽  
Ji Mingshan ◽  
Peiwen Qin
Keyword(s):  
Antioxidant Activity ◽  
Insecticidal Activity ◽  
Magnaporthe Grisea ◽  
Fungicidal Activity ◽  
Biological Activities ◽  
Citrullus Colocynthis ◽  
Mycelium Growth ◽  
Growth Inhibition Assay

Abstract Terpenoids from natural plants resources are valuable for diverse biological activities which exhibited important part in medical and agrochemicals industry. This study aimed to assess the antioxidant, antifungal and insecticidal activity of a mixture of Spinasterol, 22,23-dihydrospinasterol isolated from Citrullus colocynthis leaves. 1, 1-diphenyl-2-picrylhydrazyl (DPPH) was used to assess the antioxidant activity whereas, antifungal activity was tested by mycelium growth inhibition assay on three pathogenic fungi Magnaporthe grisea, Rhizoctonia solani and Phytophthora infestans. Insecticidal activity against Brevicoryne brassicae was also determined by using In-vitro and In-vivo assays. The outcome of the study exposed that Spinasterol, 22, 23-dihydrospinasterol afforded prominent antioxidant activity even at lower concentrations i.e. 19.98, 31.52, 36.61 and 49.76% at 0.78, 3.0, 12.5 and 50µgmL-1 respectively. However, moderate fungicidal activity of Spinasterol, 22; 23-dihydrospinasterol was recorded as being EC50 values 129.5 and 206.1µgmL-1 against R. solani and M. grisea respectively. On the other hand, Boscalid and Carbendazim being a positive control proved highly effective against all fungi except for M. grisea and P. infestans with EC50 values 868 and 272109µgmL-1 respectively. The pronounced insecticidal activity of Spinasterol, 22,23-dihydrospinasterol was afforded via residual as well as greenhouse assay being LC50 values as 42.46, 54.86, 180.9 µgmL-1 and 32.71, 42.46 and 173.8µgmL-1 at 72, 48 and 24 h respectively. The study concluded that isolated compound Spinasterol, 22,23-dihydrospinasterol possess promising antioxidant and aphicidal activity with moderate fungicidal activity which could be a suitable candidate as an alternative to synthetic pesticidal agents.

scholarly journals Structure-In Vitro Activity Relationships of Pentamidine Analogues and Dication-Substituted Bis-Benzimidazoles as New Antifungal Agents

1998 ◽  
Vol 42 (10) ◽  
pp. 2495-2502 ◽  
Author(s):  
Maurizio Del Poeta ◽  
Wiley A. Schell ◽  
Christine C. Dykstra ◽  
Susan Jones ◽  
Richard R. Tidwell ◽  
...  
Keyword(s):  
Fungicidal Activity ◽  
Antifungal Agents ◽  
In Vitro Activity ◽  
Primary Metabolites ◽  
Structure Activity ◽  
Fluconazole Resistant ◽  
Resistant Strains ◽  
Clinical Potential

ABSTRACT Twenty analogues of pentamidine, 7 primary metabolites of pentamidine, and 30 dicationic substituted bis-benzimidazoles were screened for their inhibitory and fungicidal activities againstCandida albicans and Cryptococcus neoformans. A majority of the compounds had MICs at which 80% of the strains were inhibited (MIC80s) comparable to those of amphotericin B and fluconazole. Unlike fluconazole, many of these compounds were found to have potent fungicidal activity. The most potent compound against C. albicans had an MIC80 of ≤0.09 μg/ml, and the most potent compound against C. neoformans had an MIC80 of 0.19 μg/ml. Selected compounds were also found to be active againstAspergillus fumigatus, Fusarium solani,Candida species other than C. albicans, and fluconazole-resistant strains of C. albicans and C. neoformans. It is clear from the data presented here that further studies on the structure-activity relationships, mechanisms of action and toxicities, and in vivo efficacies of these compounds are warranted to determine their clinical potential.

Structure−Activity Relationship of 2-[[(2-Pyridyl)methyl]thio]-1H- benzimidazoles as AntiHelicobacter pyloriAgents in Vitro and Evaluation of their in Vivo Efficacy

1998 ◽  
Vol 41 (11) ◽  
pp. 1777-1788 ◽  
Author(s):  
Thomas C. Kühler ◽  
Marianne Swanson ◽  
Vladimir Shcherbuchin ◽  
Håkan Larsson ◽  
Björn Mellgård ◽  
...  
Keyword(s):  
Structure Activity Relationship ◽  
Activity Relationship ◽  
In Vivo Efficacy ◽  
Structure Activity ◽  
Relationship Of

Neurotoxicity of Pesticides: The Roadmap for the Cubic Mode of Action

2020 ◽  
Vol 27 (1) ◽  
pp. 54-77 ◽  
Author(s):  
Bogdan Bumbăcilă ◽  
Mihai V. Putz
Keyword(s):  
Biological Activity ◽  
Wiener Index ◽  
Laboratory Animals ◽  
Covalent Bonds ◽  
Organophosphate Compounds ◽  
Sar Studies ◽  
Structure Activity ◽  
Cubic Structure

Pesticides are used today on a planetary-wide scale. The rising need for substances with this biological activity due to an increasing consumption of agricultural and animal products and to the development of urban areas makes the chemical industry to constantly investigate new molecules or to improve the physicochemical characteristics, increase the biological activities and improve the toxicity profiles of the already known ones. Molecular databases are increasingly accessible for in vitro and in vivo bioavailability studies. In this context, structure-activity studies, by their in silico - in cerebro methods, are used to precede in vitro and in vivo studies in plants and experimental animals because they can indicate trends by statistical methods or biological activity models expressed as mathematical equations or graphical correlations, so a direction of study can be developed or another can be abandoned, saving financial resources, time and laboratory animals. Following this line of research the present paper reviews the Structure-Activity Relationship (SAR) studies and proposes a correlation between a topological connectivity index and the biological activity or toxicity made as a result of a study performed on 11 molecules of organophosphate compounds, randomly chosen, with a basic structure including a Phosphorus atom double bounded to an Oxygen atom or to a Sulfur one and having three other simple covalent bonds with two alkoxy (-methoxy or -ethoxy) groups and to another functional group different from the alkoxy groups. The molecules were packed on a cubic structure consisting of three adjacent cubes, respecting a principle of topological efficiency, that of occupying a minimal space in that cubic structure, a method that was called the Clef Method. The central topological index selected for correlation was the Wiener index, since it was possible this way to discuss different adjacencies between the nodes in the graphs corresponding to the organophosphate compounds molecules packed on the cubic structure; accordingly, "three dimensional" variants of these connectivity indices could be considered and further used for studying the qualitative-quantitative relationships for the specific molecule-enzyme interaction complexes, including correlation between the Wiener weights (nodal specific contributions to the total Wiener index of the molecular graph) and the biochemical reactivity of some of the atoms. Finally, when passing from SAR to Q(uantitative)-SAR studies, especially by the present advanced method of the cubic molecule (Clef Method) and its good assessment of the (neuro)toxicity of the studied molecules and of their inhibitory effect on the target enzyme - acetylcholinesterase, it can be seen that a predictability of the toxicity and activity of different analogue compounds can be ensured, facilitating the in vivo experiments or improving the usage of pesticides.

Synthesis and Antitumor Activity Evaluation of New Phenanthrene-Based Tylophorine Derivatives

2019 ◽  
Vol 16 (6) ◽  
pp. 462-467
Author(s):  
Songtao Li ◽  
Hongling Zhao ◽  
Zhifeng Yin ◽  
Shuhua Deng ◽  
Yang Gao ◽  
...  
Keyword(s):  
Antitumor Activity ◽  
Cell Lines ◽  
Antitumor Activities ◽  
Human Carcinoma ◽  
Carcinoma Cell Lines ◽  
Structure Activity ◽  
Human Carcinoma Cell ◽  
Ic50 Values ◽  
Relationship Of

A series of new phenanthrene-based tylophorine derivatives (PBTs) were synthesized in good yield and their structures were characterized by 1H-NMR spectroscopy and ESI MS. In vitro antitumor activity of these compounds against five human carcinoma cell lines, including HCT116 (colorectal), BGC-823 (gastric), HepG-2 (hepatic), Hela (cervical) and H460 (lung) cells, was evaluated by MTT assay. Among these PBTs, compound 6b showed the highest antitumor activities against HCT116 and HepG-2 cell lines with IC50 values of 6.1 and 6.4 μM, respectively, which were comparable to that of adriamycin hydrochloride. The structure-activity relationship of these compounds was also discussed based on the results of their antitumor activity.

scholarly journals A Peptide Found in Human Serum, Derived from the C-Terminus of Albumin, Shows Antifungal Activity In Vitro and In Vivo

2020 ◽  
Vol 8 (10) ◽  
pp. 1627
Author(s):  
Tecla Ciociola ◽  
Pier Paolo Zanello ◽  
Tiziana D’Adda ◽  
Serena Galati ◽  
Stefania Conti ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Human Serum ◽  
Fungicidal Activity ◽  
Galleria Mellonella ◽  
Serum Proteins ◽  
Morphological Alterations ◽  
C Terminus ◽  
Different Sources

The growing problem of antimicrobial resistance highlights the need for alternative strategies to combat infections. From this perspective, there is a considerable interest in natural molecules obtained from different sources, which are shown to be active against microorganisms, either alone or in association with conventional drugs. In this paper, peptides with the same sequence of fragments, found in human serum, derived from physiological proteins, were evaluated for their antifungal activity. A 13-residue peptide, representing the 597–609 fragment within the albumin C-terminus, was proved to exert a fungicidal activity in vitro against pathogenic yeasts and a therapeutic effect in vivo in the experimental model of candidal infection in Galleria mellonella. Studies by confocal microscopy and transmission and scanning electron microscopy demonstrated that the peptide penetrates and accumulates in Candida albicans cells, causing gross morphological alterations in cellular structure. These findings add albumin to the group of proteins, which already includes hemoglobin and antibodies, that could give rise to cryptic antimicrobial fragments, and could suggest their role in anti-infective homeostasis. The study of bioactive fragments from serum proteins could open interesting perspectives for the development of new antimicrobial molecules derived by natural sources.

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