- Synthesis of a Series of Novel 2-Amino-5-substituted 1,3,4-oxadiazole and 1,3,4-thiadiazole Derivatives as Potential Anticancer, Antifungal and Anti-bacterial Agents
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Objective: The objective of the present study was to prepare the 5-substituted 2-amino-1,3,4-oxadiazole and 2-amino-1,3,4-thiadiazole derivatives and evaluate their potential anticancer, antibac-terial and antifungal activities. Methods: Twenty-seven derivatives were synthesized by iodine-mediated cyclization of semicarba-zones or thiosemicarbazones obtained from condensation of semicarbazide or thiosemicarbazide and aldehydes. The structures were confirmed by1H-NMR,13C-NMR and MS spectra. The antibacterial and antifungal activities were evaluated by diffusion method and the anticancer activities were evaluated by MTT assay. Results: Twenty-seven derivatives have been synthesized in moderate to good yields. A number of derivatives exhibited potential antibacterial, antifungal and anticancer activities. Conclusion: Compounds (1b, 1e and 1g) showed antibacterial activity against Streptococcus faecal-is, MSSA and MRSA with MIC value ranging between 4 to 64 μg/mL. Compound (2g) showed anti-fungal activity against Candida albicans (8 μg/mL) and Aspergillus niger (64 μg/mL). Compound (1o) exhibited high cytotoxic activity against HepG2 cell line (IC50 value 8.6 μM) which is compara-ble to the activity of paclitaxel, and is non-toxic on LLC-PK1 normal cell line. The structure activity relationship and molecular docking study of the synthesized compounds have also been reported.
- Do, tuoi thi Hong,Dong, Nguyen Hanh,Vo, Duy Duc,pham, Em canh,truong, tuyen Ngoc
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p. 558 - 573
(2022/03/09)
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- The design, synthesis, and: In vitro trypanocidal and leishmanicidal activities of 1,3-thiazole and 4-thiazolidinone ester derivatives
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Chagas and leishmaniasis are both neglected tropical diseases, whose inefficient therapies have made them remain the cause for millions of deaths worldwide. Given this, we synthesized 27 novel 1,3-thiazoles and 4-thiazolidinones using bioisosteric and est
- Haroon, Muhammad,De Barros Dias, Mabilly Cox Holanda,Santos, Aline Caroline da Silva,Pereira, Valéria Rêgo Alves,Freitas, Luiz Alberto Barros,Balbinot, Rodolfo Bento,Kaplum, Vanessa,Nakamura, Celso Vataru,Alves, Luiz Carlos,Brayner, Fábio André,Leite, Ana Cristina Lima,Akhtar, Tashfeen
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p. 2487 - 2500
(2021/01/29)
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- Synthesis, anti-HIV activity, molecular modeling study and QSAR of new designed 2-(2-arylidenehydrazinyl)-4-arylthiazoles
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Taking into consideration the eminence of 1,3-thiazoles in medicinal chemistry and in a view of procuring more pronounced biological contour, the synthesis of 2-(2-arylidenehydrazinyl)-4-arylthiazoles 6–43 was made possible by the cyclization reaction of thiosemicarbazones and α-bromoacetophenones. The thiosemicarbazones 5a-m were in turn synthesized from substituted benzaldehydes or acetophenones and thiosemicarbazide. Optimization of the reaction conditions was carried out in order to attain the target molecules in good yields. All the new compounds were evaluated in vitro for their antiviral activity against the replication of HIV-1 and HIV-2 in MT4 cells using a MTT assay. Screening results indicated that compounds 32–34 are the only compounds in the series inhibiting HIV-1 and HIV-2 replication in cell cultures with IC50 of >2.71, >2.19 and > 1.71 μM, respectively. The molecular docking of compounds 32 and 34 with some amino acids of human immunodeficiency virus reverse transcriptase (HIV RT) were also studied. The preliminary quantum structure-activity relationship (QSAR) among the newly synthesized congeners was obtained by two methods, Multiple Linear Regression (MRL) and Genetic Function Approximation (GFA).
- Rauf, Amna,Kashif, Muhammad K.,Saeed, Bahjat A.,Al-Masoudi, Najim A.,Hameed, Shahid
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- Synthesis and antifungal activities of drimane-amide derivatives from sclareol
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Aim and Objective: Plant diseases are caused by fungal pathogens lead to severe economic losses in many agriculture crops. And the increasing resistance of many fungi to commonly used antifungal agents necessitates the discovery and development of new fungicides. So this study was focused on synthesizing novel skeleton compounds to effectively control plant diseases. Materials and Methods: A series of drimane-amide derivatives were designed, synthesized by aminolysis reaction of amine with intermediate sclareolide which was prepared from sclareol. The structures of all the synthesized compounds were confirmed using1H NMR,13C NMR, and HR-MS (ESI) spectroscopic data. Their in vitro antifungal activity were preliminarily evaluated by using the mycelium growth rate method against five phytopathogenic fungi: Botrytis cinerea, Glomerella cingulata, Alternaria alternate, Alternaria brassicae, and Fusarium graminearum. Results: 23 target compounds were successfully obtained in yields of 52-95%. Compounds358 A2 and A3 displayed favorable inhibitory potency against B. cinerea, G. cingulata and A. brassicae with IC50 values ranging from 3.18 to 10.48 μg/mL. These two compounds displayed higher fungicidal activity than sclareol against all the tested phytopathogenic fungi, and were more effective than the positive control thiabendazole against A. alternate and A. brassicae. The structure-activity relationship studies of compounds A1-10 indicated that both the position and type of substituent on the phenyl ring had significant effects on antifungal activity. Conclusion: The drimane-amide derivatives A2 and A3 were the most promising derivatives and should be selected as new templates for the potential antifungal agents.
- Ma, Miaofeng,Feng, Jili,Wang, Dezhi,Chen, Shu-Wei,Xu, Hui
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p. 501 - 509
(2018/12/13)
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- Regioselective N(2)-H-functionalization of thiosemicarbazones of aromatic and heteroaromatic aldehydes with acrylonitrile
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Regioselective N(2)-H-cyanoethylation of thiosemicarbazones of aromatic and heteroaromatic aldehydes with acrylonitrile proceeds under mild conditions (14% KOH, acetone/H2O, 35 °C, 6–21 h) to afford 1-(2-сyanoethyl)-2-[(E)-aryl(heteroaryl)methylidene]-1-hydrazinecarbothioamides in up to 74% yields. The synthesized thioamides are promising precursors of novel families of functionalized thiosemicarbazones as exemplified by hydrolysis of their cyano group to the corresponding amido function (46.5–60% yields).
- Mal’kina, Anastasiya G.,Nosyreva, Valentina V.,Albanov, Alexander I.,Afonin, Andrei V.,Vashchenko, Alexander V.,Amosova, Svetlana V.,Trofimov, Boris A.
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supporting information
p. 159 - 168
(2017/01/10)
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- Synthesis and antimicrobial evaluation of novel 3-(arylideneamino)-3a,8a-dihydroxy-1,3,3a,8a-tetrahydroindeno[1,2-d]imidazole-2,8-diones and their 2-thioxo analogues
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The preparation of some novel 3-(arylideneamino)-3a,8a-dihydroxy-1,3,3a,8a-tetrahydroindeno[1,2-d]imidazole-2,8-diones 8(i–xiv) and 3-(arylideneamino)-3a,8a-dihydroxy-2-thioxo-1,3,3a,8a-tetrahydroindeno[1,2-d]imidazol-8(2H)-ones 9(i–xiv) have been reported through one-pot catalyst-free reaction of aldehydes, semicarbazide hydrochloride/thiosemicarbazide with ninhydrin. All the synthesized compounds have been screened for antimicrobial activity and some of them were observed to possess broad spectrum antibacterial potential as well as significant antagonistic potential against fungal pathogens.
- Saini, Yeshwinder,Khajuria, Rajni,Kaur, Ramneet,Kaul, Sanjana,Sharma, Tanwi,Gupta, Suruchi,Gupta, Vivek K.,Kant, Rajni,Kapoor, Kamal K.
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supporting information
p. 1159 - 1168
(2017/06/09)
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- Synthesis, biological evaluation and quantitative structure-active relationships of 1,3-thiazolidin-4-one derivatives. A promising chemical scaffold endowed with high antifungal potency and low cytotoxicity
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With reference to recent studies reporting on the various biological properties of the thiazolidinone scaffold, we synthesized more than a hundred compounds characterized by a 1,3-thiazolidin-4-one nucleus derivatised at the C2 with a hydrazine bridge linked to (cyclo)aliphatic or hetero(aryl) moieties, and their N-benzylated derivatives. These molecules were assayed as potential anti-Candida agents and they were shown to possess comparable, and in some cases higher biological activity than well-established topical and systemic antimycotic drugs (i.e. clotrimazole, fluconazole, ketoconazole, miconazole, tioconazole, amphotericin B). Compounds endowed with the lowest MICs underwent further testing in order to assess their cytotoxic effect (CC50) on Hep2 cells, which demonstrated their relative safety. Finally, QSAR and 3-D QSAR models were used to predict putative chemical modifications of the 1,3-thiazolidin-4-one scaffold in order to design new and potential more active compounds against Candida spp.
- Carradori, Simone,Bizzarri, Bruna,D'Ascenzio, Melissa,De Monte, Celeste,Grande, Rossella,Rivanera, Daniela,Zicari, Alessanda,Mari, Emanuela,Sabatino, Manuela,Patsilinakos, Alexandros,Ragno, Rino,Secci, Daniela
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p. 274 - 292
(2017/10/05)
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- Inhibitory effect of synthetic aromatic heterocycle thiosemicarbazone derivatives on mushroom tyrosinase: Insights from fluorescence, 1H NMR titration and molecular docking studies
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Three structurally similar aromatic heterocyclic compounds 2-thiophenecarboxaldehyde (a), 2-furaldehyde (b), 2-pyrrolecarboxaldehyde (c) were chosen and a series of their thiosemicarbazone derivatives(1a-3a, 1b-3b and 1c-3c) were synthesized to evaluate t
- Xie, Juan,Dong, Huanhuan,Yu, Yanying,Cao, Shuwen
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p. 709 - 716
(2015/06/16)
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- Anti-Candida activity and cytotoxicity of a large library of new N-substituted-1,3-thiazolidin-4-one derivatives
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On the basis of the recent findings about the biological properties of thiazolidinones and taking into account the encouraging results about the antifungal activity of some (thiazol-2-yl)hydrazines, new N-substituted heterocyclic derivatives were designed combining the thiazolidinone nucleus with the hydrazonic portion. In details, 1,3-thiazolidin-4-ones bearing (cyclo)aliphatic or (hetero)aromatic moieties linked to the N1-hydrazine at C2 were synthesized and classified into three series according to the aromatic or bicyclic rings connected to the lactam nitrogen of the thiazolidinone. These molecules were assayed for their anti-Candida effects in reference to the biological activity of the conventional topic (clotrimazole, miconazole, tioconazole) and systemic drugs (fluconazole, ketoconazole, amphotericin B). Finally, we investigated the selectivity against fungal cells by testing the compounds endowed with the best MICs on Hep2 cells in order to assess their cell toxicity (CC50) and we noticed that two derivatives were less cytotoxic than the reference drug clotrimazole. Moreover, a preliminary molecular modelling approach has been performed against lanosterol 14-α demethylase (CYP51A1) to rationalize the activity of the tested compounds and to specify the target protein or enzyme.
- De Monte, Celeste,Carradori, Simone,Bizzarri, Bruna,Bolasco, Adriana,Caprara, Federica,Mollica, Adriano,Rivanera, Daniela,Mari, Emanuela,Zicari, Alessandra,Akdemir, Atilla,Secci, Daniela
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- Efficient "on water" green route heterocyclization of thiosemicarbazones with DMAD
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A simple, efficient, and eco-friendly procedure for the synthesis of thiazolidin-4-one derivatives in water from cyclocondensation reaction of thiosemicarbazone derivatives and dimethylacetylene dicarboxylate (DMAD) in good yield is reported. The regiochemistry of the cyclized products is established by elemental analysis, IR, NMR, and mass spectral data. A single crystal X-ray diffraction study of a representative compound, 3f, is reported.
- Singla, Rohit,Gautam, Deepika,Gautam, Poonam,Chaudhary
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p. 740 - 745
(2016/05/09)
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- 5-aryl-1,3,4-thiadiazole-based hydroxamic acids as histone deacetylase inhibitors and antitumor agents: Synthesis, bioevaluation and docking study
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The search for newer histone deacetylase (HDAC) inhibitors has attracted a great deal of interest of medicinal chemists worldwide, especially after the first HDAC inhibitor (Zolinza , widely known as SAHA or Suberoylanilide hydroxamic acid) was approved by the FDA for the treatment of Tcell lymphoma in 2006. As a continuity of our ongoing research in this area, we designed and synthesized a series of 5-aryl-1,3,4-thiadiazole-based hydroxamic acids as analogues of SAHA and evaluated their biological activities. Most of the compounds in this series, e.g. compounds with 5-aryl moiety being 2-furfuryl (5a), 5-bromofuran-2-yl (5b), 5-methylfuran-2-yl (5c), thiophen-2-yl (5d), 5-methylthiophen-2-yl (5f) and pyridyl (5g-i), were found to have potent anticancer cytotoxicity with IC50 values of generally 5-to 10-fold lower than that of SAHA in 4 human cancer cell lines assayed. Those compounds with potent cytotoxicity were also found to have strong HDAC inhibition effects. Docking studies revealed that compounds 5a and 5d displayed high affinities towards HDAC2 and 8.
- Huong, Tran Thi Lan,Dung, Do Thi Mai,Oanh, Dao Thi Kim,Lan, Tran Thi Bich,Dung, Phan Thi Phuong,Loi, Vu Duc,Kim, Kyung Rok,Han, Byung Woo,Yun, Jieun,Kang, Jong Soon,Kim, Youngsoo,Han, Sang-Bae,Nam, Nguyen-Hai
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p. 296 - 304
(2016/03/22)
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- Novel 5-Aryl-1,3,4-Thiadiazole-Based Hydroxamic Acids and Anti-Cancer Composition Comprising the Same As Active Ingredient
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The present invention relates to novel 5-aryl-1,3,4-thiadiazole-based hydroxamic acid, and an anti-cancer composition containing the same as an active ingredient. The hydroxamic acid compound of the present invention shows strong activities of inhibiting histone deacetylase (HDAC) and cytotoxicity against various cancer cells, thereby being able to be developed into an active component of strong anticancer drugs.COPYRIGHT KIPO 2016
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-
Paragraph 0069-0071
(2016/11/14)
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- Synthesis of bis-thiazoles, bis-pyrazoles, bis-hydrazonates, and bis-triazolothiadiazoles based on bis-hydrazonoyl and bis-hydrazones
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A facile synthesis of bis-thiazoles, bis-pyrazoles, and bis-hydrazonates from the reaction of bis-hydrazonoyl dichlorides with different moieties is described. Bis-triazolothiadiazoles were synthesized via oxidative cyclization of bis-hydrazones. Structures of the final product were elucidated by elemental analyses and spectral data.
- Sayed, Abdelwahed
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p. 600 - 609
(2015/08/06)
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- Synthesis and pharmacological screening of a large library of 1,3,4-thiadiazolines as innovative therapeutic tools for the treatment of prostate cancer and melanoma
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Antimitotic agents are widely used in cancer chemotherapy but the numerous side effects and the onset of resistance limit their clinical efficacy. Therefore, with the purpose of discovering more selective and efficient anticancer agents to be administered alone or in combination with traditional drugs, we synthesized a large library of 1,3,4-thiadiazoline analogues, maintaining the pharmacophoric structure of an antiproliferative compound known as K858: this is a new inhibitor of kinesin Eg5, able to induce the mitotic arrest in colorectal cancer cells and in xenograft ovarian cancer cells. We screened 103 compounds to assess their antiproliferative activity on PC3 prostate cancer cell line. Two derivatives, compounds 32 (corresponding to K858) and 33, have shown to be the most effective against prostate tumor cells and also towards two melanoma cell lines (SK-MEL-5 and SK-MEL-28) at low micromolar concentrations, confirming the pharmacological activity of this scaffold and revealing the potential role of 1,3,4-thiadiazolines in the management of cancer.
- De Monte, Celeste,Carradori, Simone,Secci, Daniela,D'Ascenzio, Melissa,Guglielmi, Paolo,Mollica, Adriano,Morrone, Stefania,Scarpa, Susanna,Aglianò, Anna Maria,Giantulli, Sabrina,Silvestri, Ida
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p. 245 - 262
(2015/11/03)
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- In vitro and in silico antimalarial activity of 2-(2-hydrazinyl)thiazole derivatives
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A series of 2-(2-hydrazinyl)thiazole derivatives with a wide range of substitutions at 2-, 4- and 5-positions were synthesized, characterized and evaluated their inhibitory potentials against plasmodium falciparum, NF54, by in vitro blood stage assay. The compounds, ethyl-4-methyl-2-[(E)-2-[1-(pyridin-2- yl)ethylidene]hydrazin-1-yl]-1,3-thiazole-5-carboxylate, 4d, and 1-{4-methyl-2-[(E)-2-[1-(pyridin-2-yl)ethylidene]hydrazin-1-yl]-1, 3-thiazol-5-yl}ethan-1-one, 5d showed significant antimalarial activity with IC50 values of 0.725 μM and 0.648 μM respectively. To understand the mechanism, the binding interactions between 2-(2-hydrazinyl) thiazole derivatives and trans-2-enoyl acyl carrier protein reductase of P. falciparum were studied through docking studies. The half maximal inhibitory concentration (IC50) through docking studies for the compounds, 4d and 5d were found to be 22.88 μM and 631.84 μM respectively.
- Makam, Parameshwar,Thakur, Prasoon Kumar,Kannan, Tharanikkarasu
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p. 138 - 145
(2014/01/06)
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- Synthesis of a novel series of thiazole-based histone acetyltransferase inhibitors
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Acetylation, which targets a broad range of histone and non-histone proteins, is a reversible mechanism and plays a critical role in eukaryotic genes activation/deactivation. Acetyltransferases are very well conserved through evolution. This allows the use of a simple model organism, such as budding yeast, for the study of their related processes and to discover specific inhibitors. Following a simple yeast-based chemogenetic approach, we have identified a novel HAT (histone acetyltransferase) inhibitor active both in vitro and in vivo. This new synthetic compound, 1-(4-(4-chlorophenyl)thiazol-2- yl)-2-(propan-2-ylidene)hydrazine, named BF1, showed substrate selectivity for histone H3 acetylation and inhibitory activity in vitro on recombinant HAT Gcn5 and p300. Finally, we tested BF1 on human cells, HeLa as control and two aggressive cancer cell lines: a neuroblastoma from neuronal tissue and glioblastoma from brain tumour. Both global acetylation of histone H3 and specific acetylation at lysine 18 (H3AcK18) were lowered by BF1 treatment. Collectively, our results show the efficacy of this novel HAT inhibitor and propose the utilization of BF1 as a new, promising tool for future pharmacological studies.
- Secci, Daniela,Carradori, Simone,Bizzarri, Bruna,Bolasco, Adriana,Ballario, Paola,Patramani, Zoi,Fragapane, Paola,Vernarecci, Stefano,Canzonetta, Claudia,Filetici, Patrizia
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p. 1680 - 1689
(2014/03/21)
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- Evaluation of a large library of (thiazol-2-yl)hydrazones and analogues as histone acetyltransferase inhibitors: Enzyme and cellular studies
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Recently we described some (thiazol-2-yl)hydrazones as antiprotozoal, antifungal and anti-MAO agents as well as Gcn5 HAT inhibitors. Among these last compounds, CPTH2 and CPTH6 showed HAT inhibition in cells and broad anticancer properties. With the aim to identify HAT inhibitors more potent than the two prototypes, we synthesized several new (thiazol-2-yl)hydrazones including some related thiazolidines and pyrimidin-4(3H)-ones, and we tested the whole library existing in our lab against human p300 and PCAF HAT enzymes. Some compounds (1x, 1c', 1d', 1i' and 2m) were more efficient than CPTH2 and CPTH6 in inhibiting the p300 HAT enzyme. When tested in human leukemia U937 and colon carcinoma HCT116 cells (100 μM, 30 h), 1x, 1i' and 2m gave higher (U937 cells) or similar (HCT116 cells) apoptosis than CPTH6, and were more potent than CPTH6 in inducing cytodifferentiation (U937 cells).
- Carradori, Simone,Rotili, Dante,De Monte, Celeste,Lenoci, Alessia,D'Ascenzio, Melissa,Rodriguez, Veronica,Filetici, Patrizia,Miceli, Marco,Nebbioso, Angela,Altucci, Lucia,Secci, Daniela,Mai, Antonello
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p. 569 - 578
(2014/06/09)
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- Design, synthesis and biological characterization of thiazolidin-4-one derivatives as promising inhibitors of Toxoplasma gondii
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We designed and synthesized a large number of novel thiazolidin-4-one derivatives for the evaluation of their anti-Toxoplasma gondii activity. This scaffold was functionalized at the N1-hydrazine portion with aliphatic, cycloaliphatic and (hetero)aromatic moieties. Then, a benzyl pendant was introduced at the lactamic NH of the core nucleus to evaluate the influence of this chemical modification on biological activity. The compounds were subjected to several in vitro assays to assess their anti-parasitic efficacy, cytotoxicity on fibroblasts, inhibition of tachyzoite invasion/attachment and replication after treatment. Results showed that fourteen of these thiazole-based compounds compare favorably to control compound trimethoprim in terms of parasite growth inhibition.
- D'Ascenzio, Melissa,Bizzarri, Bruna,De Monte, Celeste,Carradori, Simone,Bolasco, Adriana,Secci, Daniela,Rivanera, Daniela,Faulhaber, Nathan,Bordón, Claudia,Jones-Brando, Lorraine
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-
- Synthesis and selective human monoamine oxidase b inhibition of heterocyclic hybrids based on hydrazine and thiazole scaffolds
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A new scaffold of hydrazothiazoles has been designed as monoamine oxidase (MAO) inhibitors combining the hydrazine moiety of iproniazid and the thiazole nucleus of glitazones, a class of peroxisome proliferator-activated receptor (PPAR)γ agonists recently co-crystallized with human MAO-B. The resulting derivatives were synthesized and assayed to evaluate their in vitro activity against both the A and B isoforms of hMAO. All compounds were shown to be selective hMAO-B inhibitors with IC50 values in the low micromolar/high nanomolar range. Such results suggest that the hydrazothiazole scaffold could be considered as an interesting pharmacophore for the future design of new lead compounds as coadjuvants for the treatment of neurodegenerative diseases. The hydrazothiazole scaffold has been designed combining the hydrazide moiety of iproniazid and the thiazole nucleus of glitazones, a class of peroxisome proliferator-activated receptor γ agonists recently co-crystallized with human monoamine oxidase B (hMAO-B). The resulting derivatives were assayed to evaluate their in vitro inhibitory activity against both the A and B isoforms of hMAO. All compounds were shown to be selective and potent hMAO-B inhibitors in the low micromolar/high nanomolar range. Copyright
- Carradori, Simone,D'Ascenzio, Melissa,De Monte, Celeste,Secci, Daniela,Yá?ez, Matilde
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- Synthesis and anti-Candida activity of novel 2-hydrazino-1,3-thiazole derivatives
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Eighteen new hydrazino-1,3-thiazole derivatives were evaluated against 8 strains of multi-resistant Candida spp. Introduction of an indolyl moiety linked to the hydrazone function enhanced the in vitro anti-Candida activity, with an activity spectrum towards Candida albicans strains. Introduction of a (S)-2-aminoethyl chain on the thiazole nucleus largely enhanced the in vitro antifungal activity, with a selectivity oriented towards non-C. albicans species.
- Maillard, Ludovic T.,Bertout, Sébastien,Quinonéro, Ophélie,Akalin, Gül?en,Turan-Zitouni, Gülhan,Fulcrand, Pierre,Demirci, Fatih,Martinez, Jean,Masurier, Nicolas
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supporting information
p. 1803 - 1807
(2013/04/10)
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- Synthesis and biological evaluation of some novel [4-(1H-Benzoimidazol-2- yl)-thiazol-2-yl]-benzylidene-amines and N-[4-(1H-Benzoimidazol-2-yl)-thiazol-2- yl]-N'-benzylidene-hydrazines
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A new family of thiazole heterocycles, namely [4-(1H-benzoimidazol-2-yl)- thiazol-2-yl]-benzylidene-amines has been synthesized by the condensation of 4-(1H-Benzoimidazol-2-yl)-thiazol-2-ylamine with various aromatic aldehydes and N-[4-(1H-benzoimidazol-2-yl)-thiazol-2-yl]-N'-benzylidene-hydrazines through the cyclization of 1-(1H-benzoimidazol-2-yl)-2-bromo-ethanone with arylthiosemicarbazones. The target compounds are achieved by using 1-(1H-Benzoimidazol-2-yl)-ethanone as starting material. The chemical structures of all newly synthesized compounds were confirmed by their IR, 1H NMR and Mass spectral data. Further the compounds were used to evaluate their antimicrobial activity and found that the appreciable antimicrobial activity by some of the title compounds.
- Mekala, Raghu Vardhan Reddy,Danda, Ravinder Reddy,Gadegoni, Hemalatha
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- Synthesis, anti-Candida activity, and cytotoxicity of new (4-(4-iodophenyl)thiazol-2-yl)hydrazine derivatives
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Novel (4-(4-iodophenyl)-thiazol-2-yl)hydrazine derivatives were assayed for their in vitro anti-Candida activity, compared to topical and systemic antifungal drugs, against twenty-seven clinical isolates. The presence of aliphatic chains or specific heteroaromatic rings on hydrazone moiety at position C2 and a 4-iodophenyl at C4 of the thiazole ring gave a promising inhibitory activity especially against Candida albicans and Candida krusei. The most active compounds have been also evaluated for their cytotoxicity and in association with clotrimazole for anti-Candida activity.
- Secci, Daniela,Bizzarri, Bruna,Bolasco, Adriana,Carradori, Simone,D'Ascenzio, Melissa,Rivanera, Daniela,Mari, Emanuela,Polletta, Lucia,Zicari, Alessandra
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experimental part
p. 246 - 253
(2012/08/28)
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- Recent advances in the development of selective human MAO-B inhibitors: (Hetero)arylidene-(4-substituted-thiazol-2-yl)hydrazines
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A large series of (4-substituted-thiazol-2-yl)hydrazine derivatives was synthesized in good yield and assayed for their in vitro human monoamine oxidase (hMAO) inhibitory activity and selectivity. Most of them showed inhibitory activity in the nanomolar range and hMAO-B selective inhibition higher than reference drugs, demonstrating our interest in this privileged scaffold. The structure-activity relationship of the different rings on the N1-hydrazine position indicated that a pyridine ring was preferred with the presence of electron-withdrawing substituents on the aryl group at C4 of the thiazole nucleus. The substituent on the α-carbon to the N1-hydrazine moiety (methyl or hydrogen) had a great influence on the activity and hMAO-B selectivity. Moreover, the reversibility of the enzyme inhibition for the best active compound was reported.
- Secci, Daniela,Bolasco, Adriana,Carradori, Simone,D'Ascenzio, Melissa,Nescatelli, Riccardo,Yá?ez, Matilde
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p. 405 - 417
(2013/02/21)
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- Refinement of arylthiosemicarbazone pharmacophore in inhibition of mushroom tyrosinase
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Melanin play a major role in human skin protection and their biosynthesis is vital. Due to their color, they contribute to the skin pigmentation. Tyrosinase is a key enzyme involved in the first stage of melanin biosynthesis, it catalyzes the transformation of tyrosine into l-dopaquinone. The aim of the present study was to study molecules able to inhibit tyrosinase to be used in treating depigmentation-related disorders. In this study, we targeted arylthiosemicarbazone analogs with the aim to contribute to the identification of the optimal aryl ring to be linked to the thiosemicarbazone moiety. The biological activity was evaluated on commercial mushroom tyrosinase which was purified prior use. The results demonstrated that several of our compounds (1a-h, 1j, 1r and 5) had more potent inhibitory activities than kojic acid which was used as the reference inhibitor.
- Yi, Wei,Dubois, Carole,Yahiaoui, Samir,Haudecoeur, Romain,Belle, Catherine,Song, Huacan,Hardre, Renaud,Reglier, Marius,Boumendjel, Ahcne
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experimental part
p. 4330 - 4335
(2011/11/06)
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- A convenient and efficient synthesis of heteroaromatic hydrazone derivatives via cyclization of thiosemicarbazone with ω-bromoacetophenone
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The synthesis of hydrazone derivatives containing thiazole unit was achieved with condensation of thiosemicarbazones and ω-bromoacetophenone at room temperature. This mild, convenient, and efficient method affords the desired products with good to excelle
- Liu, Weiwei,Tao, Chuanzhou,Tang, Lijuan,Li, Jie,Jin, Yan,Zhao, Yueqiang,Hu, Hongwen
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experimental part
p. 361 - 364
(2011/06/21)
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- Synthesis and biological evaluation of novel 2,4-disubstituted-1,3- thiazoles as anti-Candida spp. agents
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A new series of [4-(4′-substituted-phenyl)thiazol-2-yl]hydrazine derivatives were synthesized in good yield (86-99%) and characterized by elemental analysis, IR, 1H NMR, and mass spectral studies. The compounds were assayed for their in vitro broad-spectrum antifungal activity, compared to clotrimazole and fluconazole, against 20 clinical isolates of pathogenic Candida spp., representing five different species. The results showed that the presence of heterocyclic or bicyclic rings on hydrazone moiety in position C2 of thiazole revealed a promising selective inhibitory activity especially against Candida albicans and Candida glabrata.
- Chimenti, Franco,Bizzarri, Bruna,Bolasco, Adriana,Secci, Daniela,Chimenti, Paola,Granese, Arianna,Carradori, Simone,D'Ascenzio, Melissa,Lilli, Daniela,Rivanera, Daniela
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experimental part
p. 378 - 382
(2011/02/25)
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- Investigations on the 2-thiazolylhydrazyne scaffold: Synthesis and molecular modeling of selective human monoamine oxidase inhibitors
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A new series of [4-(3-methoxyphenyl)-thiazol-2-yl]hydrazyne derivatives were synthesized in good yield (71-99%) and characterized by elemental analysis and 1H NMR studies. The compounds were assayed for their in vitro human monoamine oxidase (hMAO) inhibitory activity and selectivity and most of them showed IC50 values in the nanomolar range, thus demonstrating our interest in this privileged scaffold. The most active and selective derivative (20), bearing a pyridine moiety on the CN, displayed IC50 = 3.81 ± 0.12 nM and selectivity ratio = 119 toward hMAO-B. Molecular modeling studies were carried out on recent and high resolution hMAO-A and hMAO-B crystallographic structures to better justify the enzyme-inhibitor interaction toward hMAO isoforms and to explain the structure-activity relationship of this kind of inhibitors.
- Chimenti, Franco,Bolasco, Adriana,Secci, Daniela,Chimenti, Paola,Granese, Arianna,Carradori, Simone,Yanez, Matilde,Orallo, Francisco,Ortuso, Francesco,Alcaro, Stefano
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experimental part
p. 5715 - 5723
(2010/09/09)
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- Synthesis and anti-Helicobacter pylori activity of 4-(coumarin-3-yl) thiazol-2-ylhydrazone derivatives
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A novel class of coumarin-thiazole conjugated systems (1-31) were synthesized by Hantzsch condensation between α-bromo-3-acetyl coumarin and several thiosemicarbazone intermediates. This scaffold was also evaluated for selective antibacterial activity against 20 isolates of H. pylori clinical strains, including four metronidazole resistant ones.
- Chimenti, Franco,Bizzarri, Bruna,Bolasco, Adriana,Secci, Daniela,Chimenti, Paola,Granese, Arianna,Carradori, Simone,D'Ascenzio, Melissa,Scaltrito, M. Maddalena,Sisto, Francesca
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experimental part
p. 1269 - 1274
(2011/01/05)
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- Design, synthesis and biological evaluation of hydroxy- or methoxy-substituted phenylmethylenethiosemicarbazones as tyrosinase inhibitors
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A series of hydroxy- or methoxy-substituted phenylmethylenethiosemicarbazones were designed, synthesized and evaluated as mushroom tyrosinase inhibitors. The results demonstrated that most of target compounds had remarkable inhibitory activities on mushroom tyrosinase. Interestingly, compound 2h was found to be the most potent tyrosinase inhibitor with IC50 value of 0.18 μM. The possible interaction mode between compound 2h and tyrosinase was proposed. In addition, the 1,1-diphenyl-2- picrylhydrazyl (DPPH) radical scavenging activities of select compounds (IC 5010.0 μM) were also investigated. Compounds 2d, 2e, 2h, 2i and 2l exhibited more potent DPPH radical scavenging activity than well-known antioxidants ascorbic acid (Vc) and tertiary butyl hydroquinone (TBHQ). These results suggested that such compounds might be utilized for the development of new candidate for treatment of dermatological disorders.
- Yi, Wei,Cao, Ri-Hui,Chen, Zhi-Yong,Yu, Liang,Ma, Lin,Song, Hua-Can
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experimental part
p. 1273 - 1277
(2010/05/19)
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- Synthesis and evaluation of 4-acyl-2-thiazolylhydrazone derivatives for anti-Toxoplasma efficacy in vitro
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A new series of 4-acyl-2-thiazolylhydrazone derivatives was synthesized and screened for its in vitro activity against Toxoplasma gondii. We evaluated parasite growth inhibition and cytotoxicity, inhibition of replication, and inhibition of parasite invasion of host cells. The biological results indicated that some substances had an antiproliferative effect against intracellular T. gondii tachyzoites cultivated in vitro.
- Chimenti, Franco,Bizzarri, Bruna,Bolasco, Adriana,Secci, Daniela,Chimenti, Paola,Carradori, Simone,Granese, Arianna,Rivanera, Daniela,Frishberg, Nathan,Bordón, Claudia,Jones-Brando, Lorraine
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supporting information; experimental part
p. 4574 - 4577
(2010/02/16)
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- From chemistry to biology: Furanic complexes as samples
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In order to demonstrate the links between chemistry and biology, some biological properties of a few furanic compounds have been described, starting from the synthesis and the structural characteristics. Also some features of the furan compounds with oximes; semicarbazones and thiosemicarbazones have been pointed out.
- Bouet, Gilles
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scheme or table
p. 111 - 118
(2010/10/01)
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- Furannic thiosemicarbazone complexes of Co(II), Ni(II), and Cu(II) in ethanol solutions and of Co(II) in the solid state
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Thiosemicarbazone complexes with cobalt(II), nickel(II), and copper(II) metal ions are studied in ethanol solutions. The stability constants of all the identified complexes are calculated, and we found that stability increases from cobalt to copper. The stability of the complex is increased by the presence of a donor group like methyl, whereas it is not affected by the length of the thiosemicarbazone side chain. A further study of the cobalt(II) complexes in the solid state permits the identification of the coordinating atoms. With the help of additional results from electronic spectra structures of the cobalt(II) complexes are proposed. Copyright Taylor & Francis Group, LLC.
- Jouad, El Mostapha,Bouet, Gilles M.,Khan, Mustayeen Ahmed,Dogaru, Diana,Mateescu, Constantin
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p. 2705 - 2718
(2008/03/11)
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- Synthesis of Thiosemicarbazones under Microwave Irradiation
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Thiosemicarbazones (3) are effectively synthesized in a few minutes by the condensation reaction of aldehydes with thiosemicarbazide under microwave irradiation.
- Cun-De, Wang,Jun, Lu,Xin-Zhong, Shi,Yun-Hua, Feng
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p. 3057 - 3062
(2007/10/03)
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- Symmetrisation, isomerism and structural studies on novel phenylmercury(II) thiosemicarbazonates: correlation of the energy barrier to rotation of the amino group with the bonding parameters of the thioamide group
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The reactions of phenylmercury(II) acetate with a series of alkyl, aryl and heterocyclic thiosemicarbazones in ethanol formed novel phenylmercury(II) derivatives of stoichiometry 3N2HC1(S)N1H2=cyclopentanone 1, cyclohexanone 2, benzaldehyde 3, 2-hydroxybenzaldehyde 4, 4-methoxybenzaldehyde 5, pyrrole-2-carbaldehyde 6, thiophene-2-carbaldehyde 7 or furan-2-carbaldehyde 8 thiosemicarbazone>, characterised with the help of analytical data, physical properties, IR, far-IR, multinuclear NMR (1H, 13C, 199Hg) spectroscopy and X-ray crystallography of complexes 1,5 and 6.The 1H and 13C NMR data suggest that the N2H group is deprotonated during reaction with phenylmercury(II) acetate and co-ordination occurs via the N3,S atoms in a chelating mode.The 199Hg NMR data suggest symmetrisation phenomenon for complexes 3 and 5, 2HgPh2 + , which is supported also by 1H and 13C NMR data.The δ(Hg) values reveal that shielding of Hg with the change of organic group in the thiosemicarbazones decreases in the order: 2-hydroxybenzene>>>furan>benzene>4-methoxybenzene>>thiophene ca. cyclohexanone ca. cyclopentanone>pyrrole and the Lewis basicity of the thiosemicarbazones varies in the opposite order.The 1H and 13C NMR data reveal that 7 and 8 show isomerism.There are two strong and one weak bond 3 2.489(6) 1, 2.611(7) 5, 2.492(9) Angstroem 6>, with CPh-Hg-S bond angles of 162.9(2), 174.2(3), 165.8(3) deg, respectively.The weak intermolecular interactions via Hg...N2 in 1 and via Hg...S in 5 and 6 form centrosymmetric dimers and Hg formally acquires four-co-ordination with two strong (Hg-C, Hg-S), one weak Hg...N3) and one secondary (Hg...N2 or S) bonds.The preferred dimer formation via N2 nitrogen in 1, rather than via sulfur atoms (5 and 6) despite Hg...S affinity represents an unusual bonding mode.From the low-temperature 1H NMR studies of some selected complexes, the energy barrier (ΔGTc*, Tc is coalescence temperature) to rotation of the amono group about the C1-N1 bond was calculated and correlated with bonding parameters of the thioamide group in the solid state.
- Lobana,Tarlok S.,Sanchez, Agustin,Casas, Jose S.,Castineiras, Alfonso,Sordo, Jose,et al.
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p. 4289 - 4300
(2007/10/03)
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- Synthesis and Spectral Studies on Metal Chelates of Heterocyclic Carboxaldehyde Thiosemicarbazones
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Spuare-planar neutral metal chelates of aldehyde thiosemicarbazones of the type ML2, where M=NiII, PdII or PtII and HL=thiosemicarbazone or 4-phenyl- or 4-methylthiosemicarbazone of 2-furaldehyde or thiophene-2-carboxaldeh
- Umapathy, P.,Budhkar, A. P.,Dorai, C. S.
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p. 714 - 721
(2007/10/02)
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