Journal articles: 'Imidazo[2,1-b][1,3,4]thiadiazole derivative'

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Singh, Satvir, Divya Bhandari, Monika Gupta, Chamanpreet Kaur, Anju Rani, and Sunita Devi. "SYNTHESIS, SPECTRAL STUDIES AND BIOLOGICAL ACTIVITY OF SOME IMIDAZO [2, 1-B] [1, 3, 4] THIADIAZOLE DERIVATIVES." Indian Drugs 59, no. 01 (March 7, 2022): 23–27. http://dx.doi.org/10.53879/id.59.01.12612.

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Benzoic acid substituted imidazo[2,1-b][1,3,4]thiadiazoles were synthesized using appropriate reaction scheme. The synthesized derivatives were then purified and elucidated for their structure by measuring their melting points, infra-red spectra and proton NMR spectra. The progress of the reaction was determined by using thin layer chromatography technique. The antimicrobial potential of the synthesized derivatives was evaluated against S. aureus and E. coli. The zone of inhibition (mm) was measured. Reported derivatives showed good to moderate antibacterial activity

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Abu-Hashem, Ameen Ali, and Sami A. Al-Hussain. "Design, Synthesis of New 1,2,4-Triazole/1,3,4-Thiadiazole with Spiroindoline, Imidazo[4,5-b]quinoxaline and Thieno[2,3-d]pyrimidine from Isatin Derivatives as Anticancer Agents." Molecules 27, no. 3 (January 27, 2022): 835. http://dx.doi.org/10.3390/molecules27030835.

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The current work aims to design and synthesis a new series of isatin derivatives and greatly enhances their cytotoxic activity. The derivatives 3-((bromophenyl) imino)-1-(morpholino (pyridine) methyl) indolin-2-one, 2-((oxoindoline) amino) benzoic acid, 3-(thiazolo-imino) indolinone, ethyl-2-((oxoindolin-3-ylidene)amino)-benzothiophene-3-carboxylate, 1-(oxoindoline)-benzo[4,5] thieno [2,3-d]pyrimidin-4(1H)-one, ethyl-2-(2-oxoindoline) hydrazine-1-carboxylate, N-(mercapto-oxo-pyrimidine)-2-(oxoindoline) hydrazine-1-carboxamide, N-(oxo-thiazolo[3,2-a] pyrimidine)-2-(oxoindolin-ylidene) hydrazine-carboxamide, 3-((amino-phenyl) amino)-3-hydroxy- indolinone, 3-((amino-phenyl) imino)-indolinone, 2-(2-((oxoindoline) amino) phenyl) isoindolinone, 2-(oxoindoline) hydrazine-carbothioamide, 5′-thioxospiro[indoline-3,3′-[1,2,4]triazolidin]-one, 5′-amino-spiro[indoline-3,2′-[1,3,4]thiadiazol]-2-one and 3-((2-thioxo-imidazo[4,5-b]quinoxaline) imino) indolinone were synthesized from the starting material 1-(morpholino (pyridine) methyl) indoline-2,3-dione and evaluated for their in vitro cytotoxic activity against carcinogenic cells. The new chemical structures were evidenced using spectroscopy (IR, NMR and MS) and elemental analysis. The results show that compounds imidazo[4,5-b]quinoxaline-indolinone, thiazolopyrimidine-oxoindoline, pyrimidine-oxoindoline-hydrazine-carboxamide, spiro[indoline-3,2′-[1,3,4] thiadiazol]-one and spiro[indoline-3,3′-[1,2,4]triazolidin]-one have excellent anti-proliferative activities against different human cancer cell lines such as gastric carcinoma cells (MGC-803), breast adenocarcinoma cells (MCF-7), nasopharyngeal carcinoma cells (CNE2) and oral carcinoma cells (KB).

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Rajeswar Rao, V., M. S. Rao, and T. V. Padmanabha Rao. "A novel synthesis of thiazolyl, imidazothiadiazolyl, and thiadiazinyl-2H-1-benzopyran-2-ones." Collection of Czechoslovak Chemical Communications 51, no. 10 (1986): 2214–21. http://dx.doi.org/10.1135/cccc19862214.

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3-Acetylcoumarins I with arylthiourea in the presence of iodine gave substituted 3-(2-arylamino-4-thiazolyl)-2H-1-benzopyran-2-ones (IIa-IIc). The structures of these products have been confirmed and they were converted into acetyl derivatives (IId-IIf). Condensation of various 3-(2-bromoacetyl)-2H-1-benzopyran-2-ones (III) with 2-amino-6-substituted thiadiazoles IV in the presence of ethanol and dimethylformamide yielded substituted 3-(2-substituted imidazo[2,1-b]thiadiazol-6-yl)-2H-1-benzopyran-2-ones (VI). Reaction of III with 3-substituted 4-amino-5-mercapto-S-triazole VII resulted in the formation of VIII in a single step.

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Haggam, Reda Ahmed, Mohamed Gomma Assy, Mohamed Hassan Sherif, and Mohamed Mohamed Galahom. "A series of 1,3-imidazoles and triazole-3-thiones based thiophene-2-carboxamides as anticancer agents: Synthesis and anticancer activity." European Journal of Chemistry 9, no. 2 (June 30, 2018): 99–106. http://dx.doi.org/10.5155/eurjchem.9.2.99-106.1701.

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By addition of semicarbazide or phenylhydrazine hydrochloride to thienoylisothiocyanate (1) resulted in building of thiosemicarbazide derivative (2), triazole derivative (4) and thiophene-2-carboxamide (5), respectively. Basic cyclization of compound 2 led to formation of oxadiazine (3). Synthesis of thiadiazine derivative (6) was achieved via reaction of compound 5 and maleic anhydride in triethyl amine. Heating of compound 5 with ethyl chloroacetate or sodium ethoxide produced thiadiazine derivative (7) and triazolethione (8), respectively. Thiosemicarbazide derivative 11 was synthesized by addition of nicotinic hydrazide to compound 1. Refluxing of compound 11 with lead acetate afforded triazole (13). Moreover, acid and base mediated cyclizations of compound 11 gave thiadiazole (12) and 1,2,4-triazolethione (14) throughout thiophene intermediate, respectively. Addition of ethyl 2-aminothiophene-3-carboxylate to compound 1 formed thiourea (15) which was refluxed with ethoxide giving thiophene-3-carboxylic acid (16). Lastly, nucleophilic addition of amino phenol or ethylene diamine to compound 1 yielded oxazine structure (18) and imidazole derivative (19), respectively. The yields of the synthesized compounds were 61-95%. The detailed synthesis and spectroscopic data of the new compounds are reported.

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Sowmya, A., G. N. Anil Kumar, Sujeet Kumar, and Subhas S. Karki. "The crystal structure of 6-(4-chlorophenyl)-2-(4-methylbenzyl)imidazo[2,1-b][1,3,4]thiadiazole-5-carbaldehyde." Acta Crystallographica Section E Crystallographic Communications 72, no. 10 (September 23, 2016): 1460–62. http://dx.doi.org/10.1107/s2056989016014754.

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In the title imidazo[2,1-b][1,3,4]thiadiazole derivative, C19H14ClN3OS, the 4-methylbenzyl and chlorophenyl rings are inclined to the planar imidazo[2,1-b][1,3,4]thiadiazole moiety (r.m.s. deviation = 0.012 Å) by 64.5 (1) and 3.7 (1)°, respectively. The molecular structure is primarily stabilized by a strong intramolecular C—H...O hydrogen bond, leading to the formation of a pseudo-seven-memberedS(7) ring motif, and a short intramolecular C—H...N contact forming anS(5) ring motif. In the crystal, molecules are linked by pairs of C—H...S hydrogen bonds, forming inversion dimers. The dimers are linked by C—H...O and C—H...π interactions, forming chains propagating along [110].

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Ibrahim, Yusria R. "Synthesis of imidazo- and pyrazolothiadiazoles from dithiobiureas and dimethyl ethynedicarboxylate." Journal of Chemical Research 2009, no. 10 (October 2009): 602–6. http://dx.doi.org/10.3184/030823409x12510192920270.

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Microwave irradiation of 1-substituted-2, 5-dithiobiureas and 1, 6-disubstituted-2, 5-dithiobiureas with dimethyl ethynedicarboxylate gave methyl 2-{6-oxo-2-(substituted amino)imidazo-[2, 1- b][1, 3, 5]thiadiazol-5(6 H)-ylidene} acetate and methyl 7-oxo-1, 3-bis(substituted imino)-3, 7-dihydro-1 H-pyrazolo[1, 2- c][1, 3, 4]thiadiazole-5-carboxylate. Rationales for these transformations are presented.

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Gad-Elkareem, Mohamed A. M., Azza M. Abdel-Fattah, and Mohamed A. A. Elneairy. "Pyrazolo[3,4-b]pyridine in heterocyclic synthesis: synthesis of new pyrazolo[3,4-b]pyridines, imidazo[1',2':1,5]pyrazolo[3,4-b]pyridines, and pyrido[2',3':3,4]pyrazolo[1,5-a]pyrimidines." Canadian Journal of Chemistry 85, no. 9 (September 1, 2007): 592–99. http://dx.doi.org/10.1139/v07-089.

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Pyrazolo[3,4-b]pyridine derivatives 7 and 9 were synthesized via the reaction of 3-amino-1H-pyrazolo-[3,4-b]pyridine derivative 2 with ω-bromoacetophenones. Reaction of 7 and 9 with Ac2O afforded the imidazo[1',2':1,5]py razolo[3,4-b]pyridine derivative 8 and pyrazolo[3,4-b]pyridine derivative 10, respectively. Reaction of 2 with chloroacetonitrile followed by DMF-DMA gave imidazo[1',2':1,5]pyrazolo[3,4-b]pyridines 4 and 5, respectively. Acetyl acetone and 1,1-dicyano-2,2-dimethylthioethene were reacted with 2 to afford the pyrido[2',3':3,4]pyrazolo-[1,5-a]-pyrimidines 11 and 14, respectively. Also, 2 reacted with DMF-DMA to yield the formamidine 15, which in turn, reacted with active methylene reagents, yielding the corresponding pyrido[2',3':3,4]pyrazolo[1,5-a]pyrimidines 18 and 23a-23d.Key words: 1H-pyrazolo[3,4-b]pyridines, imidazo[1',2':1,5]pyrazolo[3,4-b]pyridines, pyrido[2',3':3,4]pyrazolo[1,5-a]pyrimidines.

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Praveen, Aletti S., Hemmige S. Yathirajan, Manpreet Kaur, Badiadka Narayana, Eric C. Hosten, Richard Betz, and Christopher Glidewell. "Different patterns of supramolecular assembly in constitutionally similar 6-arylimidazo[2,1-b][1,3,4]thiadiazoles." Acta Crystallographica Section C Structural Chemistry 70, no. 9 (August 28, 2014): 920–26. http://dx.doi.org/10.1107/s2053229614018762.

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Four imidazo[2,1-b][1,3,4]thiadiazoles containing a simply-substituted 6-aryl group have been synthesized by reaction of 2-amino-1,3,4-thiadiazoles with bromoacetylarenes using microwave irradiation and brief reaction times. 6-(2-Chlorophenyl)imidazo[2,1-b][1,3,4]thiadiazole, C10H6ClN3S, (I), 6-(2-chlorophenyl)-2-methylimidazo[2,1-b][1,3,4]thiadiazole, C11H8ClN3S, (II), 6-(3,4-dichlorophenyl)imidazo[2,1-b][1,3,4]thiadiazole, C10H5Cl2N3S, (III), and 6-(4-fluoro-3-methoxyphenyl)-2-methylimidazo[2,1-b][1,3,4]thiadiazole, C12H10FN3OS, (IV), crystallize withZ′ values of 2, 1, 1 and 2 respectively. The molecular skeletons are all nearly planar and the dihedral angles between the imidazole and aryl rings are 1.51 (8) and 7.28 (8)° in (I), 9.65 (7)° in (II), 10.44 (8)° in (III), and 1.05 (8) and 7.21 (8)° in (IV). The molecules in (I) are linked by three independent C—H...N hydrogen bonds to form ribbons containing alternatingR22(8) andR44(18) rings, and these ribbons are linked into a three-dimensional array by three independent π-stacking interactions. Both (II) and (III) contain centrosymmetric dimers formed by π-stacking interactions but hydrogen bonds are absent, and the molecules of (IV) are linked into centrosymmetricR22(8) dimers by C—H...N hydrogen bonds. Comparisons are made with a number of related compounds.

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Dubey, Sonal, and Pradnya A. Bhosle. "Quantitative Structure Activity Relationship of 2, 5, 6–Trisubstituted imidazo (2, 1-b)-1, 3, 4–Thiadiazole as Anticancer Compunds." Indian Journal of Pharmaceutical Education and Research 50, no. 1 (January 1, 2016): 198–204. http://dx.doi.org/10.5530/ijper.50.1.24.

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Hassaneen, Huwaida M. E., and Richard M. Pagni. "Synthesis of New 3-Substituted Indole Derivatives." Zeitschrift für Naturforschung B 65, no. 12 (December 1, 2010): 1491–97. http://dx.doi.org/10.1515/znb-2010-1213.

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Treatment of 3-cyanoacetyl-2-methylindole (1) with phenyl isothiocyanate gave the corresponding thioacetanilide derivative 3. The thioacetanilide 3 was utilized as the key intermediate for the synthesis of some new 1,3,4-thiadiazole (6a, b and 9a - e), thiophene (11a, b), thiazolidin-4-one (4), thiazole (12 and 13), and benzothiazole (15) derivatives. The structures of the new compounds were elucidated on the basis of elemental analyses and spectral data.

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Singh, Yashveer, Baljeet Kaur, Amandeep Kaur, Vivek Kumar Gupta, and Monika Gupta. "Synthesis, spectral studies and biological activity of 2, 3-disubstituted imidazo [2, 1-b] benzothiazole derivatives." Indian Journal of Pharmaceutical and Biological Research 6, no. 01 (March 25, 2018): 01–08. http://dx.doi.org/10.30750/ijpbr.6.1.1.

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Benzothiazole is a heterocyclic compound formed by the fusion of benzene and thiazole ring. The moiety had been reported to act via competing with ATP binding site at the catalytic domain of tyrosine kinase. The present work involves the synthesis and biological evaluation of 4, 5 disubstituted imidazo [2, 1-b] benzothiazole derivatives. The antimicrobial activity of the synthesized derivatives was carried out against Gram + ve bacteria Staphylococcus aureus (MTCC 3160) and Gram –ve bacteria Bordetella bronchiseptica (MTCC 6838), Pseudomonas aeruginosa (T11) and fungal strains Candida albicans (MTCC 1637). Ciprofloxacin and Fluconazole were used as standard drug for antibacterial and antifungal activity respectively. The compounds 6a1, 6a2, 6a3, 6b1 and 8a1 exhibited good antimicrobial activity against all the strains. The derivative 8a1 was further screened for anticancer activity against MCF-7 cell line using Doxorubicin as standard. The structures of the synthesized compounds were established by IR and NMR spectral studies.

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Štefan, Leo, Ana Čikoš, Robert Vianello, Ivica Đilović, Dubravka Matković-Čalogović, and Miljenko Dumić. "Chemistry of Spontaneous Alkylation of Methimazole with 1,2-Dichloroethane." Molecules 26, no. 22 (November 21, 2021): 7032. http://dx.doi.org/10.3390/molecules26227032.

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Spontaneous S-alkylation of methimazole (1) with 1,2-dichloroethane (DCE) into 1,2-bis[(1-methyl-1H-imidazole-2-yl)thio]ethane (2), that we have described recently, opened the question about its formation pathway(s). Results of the synthetic, NMR spectroscopic, crystallographic and computational studies suggest that, under given conditions, 2 is obtained by direct attack of 1 on the chloroethyl derivative 2-[(chloroethyl)thio]-1-methyl-1H-imidazole (3), rather than through the isolated stable thiiranium ion isomer, i.e., 7-methyl-2H, 3H, 7H-imidazo[2,1-b]thiazol-4-ium chloride (4a, orthorhombic, space group Pnma), or in analogy with similar reactions, through postulated, but unproven intermediate thiiranium ion 5. Furthermore, in the reaction with 1, 4a prefers isomerization to the N-chloroethyl derivative, 1-chloroethyl-2,3-dihydro-3-methyl-1H-imidazole-2-thione (7), rather than alkylation to 2, while 7 further reacts with 1 to form 3-methyl-1-[(1-methyl-imidazole-2-yl)thioethyl]-1H-imidazole-2-thione (8, monoclinic, space group P 21/c). Additionally, during the isomerization of 3, the postulated intermediate thiiranium ion 5 was not detected by chromatographic and spectroscopic methods, nor by trapping with AgBF4. However, trapping resulted in the formation of the silver complex of compound 3, i.e., bis-{2-[(chloroethyl)thio]-1-methyl-1H-imidazole}-silver(I)tetrafluoroborate (6, monoclinic, space group P 21/c), which cyclized upon heating at 80 °C to 7-methyl-2H, 3H, 7H-imidazo[2,1-b]thiazol-4-ium tetrafluoroborate (4b, monoclinic, space group P 21/c). Finally, we observed thermal isomerization of both 2 and 2,3-dihydro-3-methyl-1-[(1-methyl-1H-imidazole-2-yl)thioethyl]-1H-imidazole-2-thione (8), into 1,2-bis(2,3-dihydro-3-methyl-1H-imidazole-2-thione-1-yl)ethane (9), which confirmed their structures.

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Wang, Xiu-Yan, Yu He, and Fei-Fei Liu. "Two New Cd(II) and Co(II) Coordination Polymers Based on a 1,10- Phenanthroline Derivative and Tri- or Tetra-Carboxylates: Syntheses, Structures and Photoluminesce." Zeitschrift für Naturforschung B 67, no. 5 (May 1, 2012): 459–64. http://dx.doi.org/10.5560/znb.2012-0029.

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Two new coordination polymers constructed with the 1,10-phenanthroline derivative 2-(2-chloro- 6-fluorophenyl)-1H-imidazo[4,5-f][1,10]-phenanthroline (L) and different carboxylates, namely, [Cd2(L)2(1,3,5-BTC)(Cl)]·H2O (1) and [Co2(L)2(1,2,4,5-BTC)(H2O)2] (2), have been synthesized under hydrothermal conditions (1,3,5-BTC = 1,3,5-benzenetricarboxylate anion and 1,2,4,5-BTC = 1,2,4,5-benzenetetracarboxylate anion). Crystal data for 1: C47H25Cd2Cl3F2N8O7, triclinic, space group P¯1, a = 10:1084(5), b = 14:9285(7), c = 15:2930(4)Å , α = 72:1050(10), β = 86:160(2), γ = 79:6000(10)°, V = 2159:88(16) °A3, Z = 2. Crystal data for 2: C24H13ClCoFN4O5, triclinic, space group P1¯, a = 7:4767(15), b = 10:094(2), c = 14:772(3)Å , α = 91:23(3), β = 100:95(3), γ = 106:57(3)°, V = 1045:8(4) Å3, Z = 2. Their crystal structures have been determined by singlecrystal X-ray diffraction analyses, and the compounds further characterized by physico-chemical and spectroscopic methods. In 1, each 1,3,5-BTC anion connects five Cd(II) atoms to form a double chain. These chains are extended into 2D supramolecular networks through μ - μ interactions. N-H...Cl, N - H...O and O - H...N hydrogen bonding interactions further stabilize the network of 1. In 2, each 1,2,4,5-BTC anion bridges four Co(II) atoms to yield a chain. μ-μ interactions among adjacent chains result in a 2D supramolecular architecture.

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A. Khalil, Mohamed, Samia M. Sayed, and Mohamed A. Raslan. "Reactivity of 2-Cyano-N-(4-(1-Methyl-1H-benzo[d]imidazol-2-yl)-3-(Methylthio)-1-Phenyl-1H-Pyrazol-5-yl)Acetamide: A Facile Synthesis of Pyrazole, Thiazole, 1,3,4-Thiadiazole and Polysubstituted Thiophene Derivatives." American Journal of Organic Chemistry 2, no. 6 (December 1, 2012): 161–70. http://dx.doi.org/10.5923/j.ajoc.20120206.06.

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Dróżdż, Agnieszka, Adrianna Sławińska-Brych, Dominika Kubera, Magdalena Kimsa-Dudek, Joanna Magdalena Gola, Jolanta Adamska, Celina Kruszniewska-Rajs, et al. "Effect of Antibiotic Amphotericin B Combinations with Selected 1,3,4-Thiadiazole Derivatives on RPTECs in an In Vitro Model." International Journal of Molecular Sciences 23, no. 23 (December 3, 2022): 15260. http://dx.doi.org/10.3390/ijms232315260.

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4-(5-methyl-1,3,4-thiadiazole-2-yl) benzene-1,3-diol (C1) and 4-[5-(naphthalen-1-ylmethyl)-1,3,4-thiadiazol-2-yl] benzene1,3-diol (NTBD) are representative derivatives of the thiadiazole group, with a high antimycotic potential and minimal toxicity against normal human fibroblast cells. The present study has proved its ability to synergize with the antifungal activity of AmB. The aim of this work was to evaluate the cytotoxic effects of C1 or NTBD, alone or in combination with AmB, on human renal proximal tubule epithelial cells (RPTECs) in vitro. Cell viability was assessed with the MTT assay. Flow cytometry and spectrofluorimetric techniques were used to assess the type of cell death and production of reactive oxygen species (ROS), respectively. The ELISA assay was performed to measure the caspase-2, -3, and -9 activity. ATR-FTIR spectroscopy was used to evaluate biomolecular changes in RPTECs induced by the tested formulas. The combinations of C1/NTBD and AmB did not exert a strong inhibitory effect on the viability/growth of kidney cells, as evidenced by the negligible changes in the apoptotic/necrotic rate and caspase activity, compared to the control cells. Both NTBD and C1 displayed stronger anti-oxidant activity when combined with AmB. The relatively low nephrotoxicity of the thiadiazole derivative combinations and the protective activity against AmB-induced oxidative stress may indicate their potential use in the therapy of fungal infections.

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Wang, Xiu-Yan, Jia Guo, Hui-Lian Wang, and Qing-Wei Wang. "Synthesis and Crystal Structure of a New Pb(II) Coordination Polymer Constructed by a 1,10-Phenanthroline Derivative and a Flexible Dicarboxylate." Zeitschrift für Naturforschung B 66, no. 6 (June 1, 2011): 647–50. http://dx.doi.org/10.1515/znb-2011-0614.

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The new coordination polymer, [Pb(L)(trans-1,4-chdc)] 1 (L = 1-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)- naphthalen-2-ol and trans-1,4-H2chdc = trans-1,4-cyclohexanedicarboxylic acid), has been hydrothermally synthesized and characterized by elemental analysis, IR spectroscopy and single-crystal X-ray diffraction. Crystal data: C31H24N4O5Pb, monoclinic, space group P21/c, a = 13.579(2), b = 9.7831(15), c = 19.958(3) Å, β = 105.058(2)°, V = 2560.3(7) Å3, Z = 4. The Pb(II) atoms are bridged by the flexible trans-1,4-chdc ligands to form a zigzag chain. The ligands L are located on both sides of the zigzag chains, where π-π interactions among neighboring zigzag chains give rise to a two-dimensional supramolecular network. In addition, O-H···O and N-H···O hydrogen bonding interactions further stabilize the supramolecular network structure of 1.

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Rashdan, Huda R. M., Mohamad T. Abdelrahman, Ihsan A. Shehadi, Sara S. El-Tanany, and Bahaa A. Hemdan. "Novel Thiadiazole-Based Molecules as Promising Inhibitors of Black Fungi and Pathogenic Bacteria: In Vitro Antimicrobial Evaluation and Molecular Docking Studies." Molecules 27, no. 11 (June 4, 2022): 3613. http://dx.doi.org/10.3390/molecules27113613.

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Novel 1,3,4-thiadiazole derivatives were synthesized through the reaction of methyl 2-(4-hydroxy-3-methoxybenzylidene) hydrazine-1-carbodithioate and the appropriate hydrazonoyl halides in the presence of a few drops of diisopropylethylamine. The chemical structure of the newly fabricated compounds was inferred from their microanalytical and spectral data. With the increase in microbial diseases, fungi remain a devastating threat to human health because of the resistance of microorganisms to antifungal drugs. COVID-19-associated pulmonary aspergillosis (CAPA) and COVID-19-associated mucormycosis (CAM) have higher mortality rates in many populations. The present study aimed to find new antifungal agents using the disc diffusion method, and minimal inhibitory concentration (MIC) values were estimated by the microdilution assay. An in vitro experiment of six synthesized chemical compounds exhibited antifungal activity against Rhizopus oryzae; compounds with an imidazole moiety, such as the compound 7, were documented to have energetic antibacterial, antifungal properties. As a result of these findings, this research suggests that the synthesized compounds could be an excellent choice for controlling black fungus diseases. Furthermore, a molecular docking study was achieved on the synthesized compounds, of which compounds 2, 6, and 7 showed the best interactions with the selected protein targets.

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Shyu, Ren-Shi, Themmila Khamrang, Joen-Rong Sheu, Chih-Wei Hsia, Marappan Velusamy, Chih-Hsuan Hsia, Duen-Suey Chou, and Chao-Chien Chang. "Ir-6: A Novel Iridium (III) Organometallic Derivative for Inhibition of Human Platelet Activation." Bioinorganic Chemistry and Applications 2018 (2018): 1–14. http://dx.doi.org/10.1155/2018/8291393.

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Platelet activation has been reported to play a major role in arterial thrombosis, cancer metastasis, and progression. Recently, we developed a novel Ir(III)-based compound, [Ir(Cp∗)1-(2-pyridyl)-3-(4-dimethylaminophenyl)imidazo[1,5-a]pyridine Cl]BF4or Ir-6 and assessed its effectiveness as an antiplatelet drug. Ir-6 exhibited higher potency against human platelet aggregation stimulated by collagen. Ir-6 also inhibited ATP-release, intracellular Ca2+mobilization, P-selectin expression, and the phosphorylation of phospholipase Cγ2 (PLCγ2), protein kinase C (PKC), v-Akt murine thymoma viral oncogene (Akt)/protein kinase B, and mitogen-activated protein kinases (MAPKs), in collagen-activated platelets. Neither the adenylate cyclase inhibitor SQ22536 nor the guanylate cyclase inhibitor 1H-[1,2,4]oxadiazolo[4,3-a]quinoxalin-1-one significantly reversed the Ir-6-mediated inhibition of collagen-induced platelet aggregation. Moreover, Ir-6 did not considerably diminish OH radical signals in collagen-activated platelets or Fenton reaction solution. At 2 mg/kg, Ir-6 markedly prolonged the bleeding time in experimental mice. In conclusion, Ir-6 plays a crucial role by inhibiting platelet activation through the inhibition of signaling pathways, such as the PLCγ2–PKC cascade and the subsequent suppression of Akt and MAPK activation, thereby ultimately inhibiting platelet aggregation. Therefore, Ir-6 is a potential therapeutic agent for preventing or treating thromboembolic disorders or disrupting the interplay between platelets and tumor cells, which contributes to tumor cell growth and progression.

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Shehata, Medhat, Susanne Schnabl, Dita Demirtas, Stefanie Tauber, Martin Hilgarth, Martin Bilban, Katrina Vanura, et al. "Effective Targeting of the PI3-K Pathway in CLL with NVP-BEZ235, a Novel Orally Available Dual PI3K/mTOR Inhibitor." Blood 112, no. 11 (November 16, 2008): 3166. http://dx.doi.org/10.1182/blood.v112.11.3166.3166.

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Abstract There is growing evidence that the anti-apoptotic PI3-K/Akt pathway is involved in pathogenesis and progression of different types of cancer. We have evidence that PI3-K inhibitors such as LY294002 and wortmannin selectively induce apoptosis in CLL cells (Shehata et al Ab. Blood 2006). Recently, a new orally available PI3-K inhibitor, NVP-BEZ235 has been developed. This competitive ATP binding imidazo-quinoline derivative is already in phase I trials against solid tumors. Here we show, for the first time, the effects of NVP-BEZ235 on the viability of CLL cells in vitro. Primary CLL cells from 37 patients were investigated. Sixteen patients were in Binet stage C, 14 in B and 7 in stage A. Seventeen patients had mutated IgVH genes, 15 had unmutated IgVH and mutation status from 5 patients was not available. Fluorescence in situ hybridization (FISH) analysis showed that 23 patients had del(13q), 9 had del(17p), 8 had del(11q) and 4 patients had trisomy 12. Nineteen patients were untreated and 18 patients were previously treated. To overcome the experimental artifact due to the spontaneous apoptosis of CLL cells in vitro, which may mask the actual effect of the tested drugs, we applied a co-culture model using human bone marrow stromal fibroblasts which supports survival of CLL cells ex vivo. CLL cells were exposed to NVP-BEZ235 at different concentrations (1 nM-10 μM) and incubation times (1, 3, 7 days). Cell viability was assessed by annexin-V/propidium iodide staining, flow cytometry and MTT assays. The results showed that cell viability was significantly higher in co-cultures compared to suspension cultures (the percentage of apoptotic cells after 3 days in co-culture was 5±4 compared to 23±12 in suspension cultures, p< 0,01). NVP-BEZ235 induced apoptosis in the majority of CLL samples under both experimental conditions. However, this effect tends to be more remarkable in co-culture than in suspension: 4-10 fold versus 3-fold increase in apoptosis rate respectively. The pro-apoptotic effect was dose and time dependent and could be observed within 16 hours after incubation at 10 nM. A maximum effect was obtained at a concentration of 5–10 μM. The IC50 values varied between patients and were in a range of 250–750 nM. At these concentrations, NVP-BEZ235 was significantly more effective in induction of apoptosis than LY294002. NVP-BEZ235 inhibited the adhesion of CLL cells to stromal cells suggesting that it may interfere with the survival signal provided by the lymphoid microenvironment in addition to its direct effect on the leukemic cells. FACS analysis demonstrated that NVB-BEZ235 specifically targets the leukemic CD19+ cells while a minimal effect on the viability of T cells and monocytes could be observed. The pro-apoptotic effect of NVP-BEZ235 was independent from the mutational status and cytogenetics. In addition, it induced apoptosis in vitro in CLL cells from patients resistant to fludarabine treatment. In parallel to induction of apoptosis in CLL cells, western blotting demonstrated that NVP-BEZ235 significantly inhibited Akt phosphorylation at Ser-473. This effect was also associated with dephosphorylation (activation) of the tumor suppressor PTEN at Ser-380. DNA microarray analysis using Affymetrix U133A Plus 2.0 GeneChips revealed more than 200 genes which were at least 2 fold up- or down-modulated by NVP-BEZ235 in vitro. These genes include LY9, DUSP10, CCR6, RGS2, IRS2, PI4K2A, ISG20, TFRC, EGR1, HSP90, LCK, TNFRSF17, LYZ, TGFBI and TLR10. In conclusion, the results demonstrate a significant and selective pro-apoptotic effect of NVP-BEZ235 in CLL cells. The data point also to the validity of PI3K-pathway inhibition as a novel therapeutic concept for CLL which should be evaluated in clinical trials.

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Hjouji, Mohammed Yassin, Joel T. Mague, Youssef Kandri Rodi, Younes Ouzidan, and El Mokhtar Essassi. "Ethyl 2-(6-bromo-2-phenyl-3H-imidazo[4,5-b]pyridin-3-yl)acetate." IUCrData 1, no. 12 (December 20, 2016). http://dx.doi.org/10.1107/s2414314616019994.

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The title imidazo [4,5-b] pyridine derivative, C16H14BrN3O2, crystallizes with two independent molecules (1 and 2) in the asymmetric unit. In molecule 1, the pendant phenyl ring is inclined to the imidazo[4,5-b]pyridine core by 43.10 (4)° while in molecule 2 the corresponding angle is 49.43 (4)°. The two molecules differ primarily in the conformations of the ester substituents. In the crystal, molecules are linkedviaC—H...N and C—H...O hydrogen bonds, forming sheets parallel to theabplane.

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Journal articles on the topic 'Imidazo[2,1-b][1,3,4]thiadiazole derivative'

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