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Автор: Grafiati

Опубліковано: 1 липня 2022

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1

Mohareb, Rafat M., Amira E. M. Abdallah, and Ebtsam A. Ahmed. "Synthesis and cytotoxicity evaluation of thiazole derivatives obtained from 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene- 3-carbonitrile." Acta Pharmaceutica 67, no. 4 (December 20, 2017): 495–510. http://dx.doi.org/10.1515/acph-2017-0040.

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Abstract Reactivity of 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3- carbonitrile towards thioglycolic acid resulted in thiazole derivative 1. The latter reacted with different chemical reagents to give thiazole, pyrano[2,3-d]thiazole and thiazolo[ 4,5-d]thiazole derivatives. Cytotoxicity effects of the newly synthesized products against six cancer cell lines, namely, human gastric cancer (NUGC), human colon cancer (DLD- 1), human liver cancer (HA22T and HEPG-2), human breast cancer (MCF) and nasopharyngeal carcinoma (HONE-1) as well as against a normal fibroblast cell (WI-38) were evaluated. The study showed that the 4,5,6,7 tetrahydrobenzo[ b] thiophene derivatives 6a, 7, 8a,b, 9b and 10b,c w ere t he most active compounds. Their potencies were attributed to the presence of the electron withdrawing groups.

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2

Andreani, Aldo, Mirella Rambaldi, and Alessandra Locatelli. "Herbicidal activity of 5-haloimidazo[2,1-b]thiazoles." Collection of Czechoslovak Chemical Communications 56, no. 11 (1991): 2430–35. http://dx.doi.org/10.1135/cccc19912430.

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3

Molina, Pedro, Antonio Arques, Maria de los Desamparados Velasco, and Jos� Manuel Villalgordo. "Fused Thiazoles from 3-Amino-thiazoline-2-thiones: Synthesis of Pyrazolo[5,1-b]thiazole and Thiazolo[2,3-b]-1,3,4-thiadiazine Derivatives." HETEROCYCLES 26, no. 5 (1987): 1323. http://dx.doi.org/10.3987/r-1987-05-1323.

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4

Jaberi, Hamid Reza, and Hadi Noorizadeh. "Synthesis of Some Novel Fused Imidazo [2, 1-b] [1, 3] Thiazole and Imidazo [2, 1-b] Thiazolo [5, 4-d] Isoxazole Derivatives." E-Journal of Chemistry 9, no. 3 (2012): 1518–25. http://dx.doi.org/10.1155/2012/896454.

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Анотація:

In this work we describe the synthesis of some novel fused imidazo [2, 1-b] [1, 3] thiazole derivatives. The reaction of 1, 2-diaminoethane 1 with carbon disulphide in H2O/ETOH as solvent furnishes 4, 5-dihydro-1H-imidazol-2-thiol 2 under reflux condition. the reaction of 4,5-dihydro-1H-imidazol-2-thiol on treatment with ethylchloro acetate and aromatic aldehyde in presence of anhydrous sodium acetate and acetic acid as solvent to give (Z)-2-(arylidene)-5,6-dihydroimidazo [2,1-b] [1,3] thiazol-3(2H)-one 3a-j. Compounds 3a-j was condensed with hydroxylamine to give 3-(aryl)-2, 3, 6, 7-tetrahydroimidazo [2, 1-b] [1,3] thiazolo [5, 4-d] isoxazole 4a-j. The structures of the new compounds were established by elemental analyses, IR,1H NMR and13C NMR data.

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5

Lan, Zheng, and Wang. "2-(3,5-Dimethyl-1H-pyrazol-1-yl)thiazolo[4,5-b]pyridine." Molbank 2019, no. 3 (August 20, 2019): M1077. http://dx.doi.org/10.3390/m1077.

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Анотація:

The compound 2-(3,5-dimethyl-1H-pyrazol-1-yl)thiazolo[4,5-b]pyridine (1) was synthesized with a yield of 71% by the reaction of 1-(thiazolo[4,5-b]pyridine-2-yl)hydrazine and acetylacetone. The structure was characterized by a single-crystal X-ray structure determination as well as 1H and 13C{1H} NMR spectroscopy. X-ray crystallography on 1 confirms the molecule consists of a pyridine–thiazole moiety and the pyrazole ring, and all non-hydrogen atoms are planar.

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6

Özbey, Süheyla, and Asiye Meriç. "3,4-Di-p-tolyl-6,7-dihydroimidazo[2,1-b][1,3]thiazole." Acta Crystallographica Section E Structure Reports Online 62, no. 7 (June 14, 2006): o2717—o2719. http://dx.doi.org/10.1107/s160053680602099x.

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The title compound, C19H18N2S, is a member of a new series of 2,3-dihydroimidazo[2,1-b][1,3]thiazoles and was obtained from 4,5-di-p-tolyl-1,3-dihydroimidazole-2-thione and 1-bromo-2-chloroethane. The thiazole ring adopts an envelope conformation; the plane through N, S and two C atoms makes a dihedral angle of 2.35 (3)° with the fused imidazole ring. The tolyl groups are essentially planar.

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7

El-Hagrassey, Eman A., Ehab Abdel-Latif, and Gamal M. Abdel-Fattah. "Synthesis and efficiency of new pyridine, chromene and thiazole containing compounds as antimicrobial and antioxidant agents." Bulletin of the Chemical Society of Ethiopia 36, no. 1 (March 28, 2022): 137–48. http://dx.doi.org/10.4314/bcse.v36i1.12.

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ABSTRACT. The versatile scaffold, N'-(2-cyanoacetyl)-2-hydroxybenzohydrazide (3) was utilized in the production of new pyridine, chromene and thiazole derivatives as antimicrobial and antioxidant agents. The synthetic strategy involves the treatment of precursor 3 with various arylidene-malononitrile and 3-aryl-2-cyanoacrylate compounds to furnish substituted pyridines 5 and 7. The interaction of 3 with salicylaldehyde and/or phenyl isothiocyanate followed by cyclization with chloroacetone produced the corresponding 2-imino-2H-chromene-3-carbohydrazide and (thiazol-2-ylidene-acetyl)-salicylic acid hydrazide compounds 8 and 9, respectively. The structural features of the synthesized compounds were confirmed by using spectroscopic methods such as (IR, 1H NMR, 13C NMR and MS). The new pyridine, chromene and thiazole products showed potent antioxidants and antimicrobial activities. The thiazole derivative 9 exhibited the highest anti-bacterial and antifungal activities against S. aureus (75.0%) and B. subtilis (73.9%) and C. albicans (66.6%). The combination between salicylic acid hydrazide and thiazole moieties in the hybrid 9 indicated the best antioxidant activity (87.9%). KEY WORDS: Salicylic hydrazide, Arylidene-malononitrile, Pyridine, Thiazole, Antioxidant Bull. Chem. Soc. Ethiop. 2022, 36(1), 137-148. DOI: https://dx.doi.org/10.4314/bcse.v36i1.12

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8

Shaik, Siddiq P., Telukutta S. Reddy, Satish Sunkari, Ayinampudi V. S. Rao, Korrapati S. Babu, Suresh K. Bhargava, and Ahmed Kamal. "Synthesis of Benzo[d]imidazo[2,1-b]thiazole-Propenone Conjugates as Cytotoxic and Apoptotic Inducing Agents." Anti-Cancer Agents in Medicinal Chemistry 19, no. 3 (June 25, 2019): 347–55. http://dx.doi.org/10.2174/1871520619666181127112621.

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Background: Cancer can be considered as a disease in which normal cells start behaving badly, multiplying uncontrollably, ignoring signals to stop and accumulating to form a mass that is generally termed as a tumor. Apoptosis or programmed cell death is a physiological process that enables organisms to control their cell numbers in many developmental and physiological settings and to eliminate unwanted cells and it plays essential role in chemotherapy-induced tumor-cell killing. The correct balance between apoptosis and inhibition of apoptosis is important in animal development as well as in tissue homeostasis. The aim of this paper is to introduce the readers about the design strategy and synthesis of effective cytotoxic and apoptotic inducing agents based on benzo[d]imidazo[2,1-b]thiazole scaffold. Methods: Benzo[d]imidazo[2,1-b]thiazole-propenone conjugates were synthesized by the condensation of 7- methoxy-2-(aryl)benzo[d]imidazo[2,1-b]thiazol-3-yl)prop-2-yn-1-ones with aryl/hetero aryl amines in ethanol at room temperature. These in turn were obtained from 7-methoxy-2-(aryl)benzo[d]imidazo[2,1-b]thiazole-3- carbaldehydes on treatment with ethynylmagnesium bromide followed by oxidation. Results: 3-Arylaminopropenone linked 2-arylbenzo[d]imidazo[2,1-b]thiazole conjugates prepared in this investigation exhibited significant cytotoxic activity and arrested HeLa cancer cells in G1 phase. The treatment of the conjugate led to 40% of loss of mitochondrial membrane potential (DΨm) in HeLa cells and 4 fold increase in the levels of reactive oxygen species (ROS). In addition, it induces apoptosis in HeLa cells, this was examined by the wound healing assay, Actin filaments and Hoechst staining assay. Conclusion: The encouraging biological profile exhibited by these 3-arylaminopropenone 2-aryl linked benzo[d]imidazo[2,1-b]thiazole conjugates demonstrate that they have the potential to be developed as a lead by further structural modifications to obtain potential chemotherapeutic agents that are likely to target the HeLa cancer cells.

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9

Lei, Jiaying, Xinliang Fu, Yulin Huang, and Xiaofang Li. "Synthesis of spiro[benzo[4,5]imidazo[2,1-b][1,3]thiazole-2,3-thiolane]s via sulfa-Michael/aldol cascade reactions." Journal of Chemical Research 43, no. 1-2 (January 2019): 63–66. http://dx.doi.org/10.1177/1747519819831898.

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The sulfa-Michael/aldol cascade reaction of ( Z)-2-arylmethylidene-benzo[4,5]imidazo[2,1- b]thiazol-3(2H)-ones and 1,4-dithiane-2,5-diol afforded novel 2-aryl-4-hydroxy-spiro[benzo[4,5]imidazo[2,1- b][1,3]thiazole-2,3-thiolan]-3-ones in moderate yields. The structures of all the products were characterized thoroughly by nuclear magnetic resonance, infrared and high-resolution mass spectrometry together with X-ray crystallographic analysis.

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10

Gobala Krishnan P, Gnanaprakash K, and Chandrasekhar KB. "Design, synthesis, characterization and antitubercular activity of some nov-el 2, 4-disubstituted thiazole derivatives." International Journal of Research in Pharmaceutical Sciences 10, no. 2 (April 23, 2019): 1504–9. http://dx.doi.org/10.26452/ijrps.v10i2.729.

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Literature reviews reveal that thiazole and pyrazine carboxamide derivatives exhibit anticonvulsant, antimicrobial, anticancer and anti-tubercular activities due to the presence of –S-C=N- and-CO–NH- moiety. A series of thiazolyl pyrazine carboxamide derivatives (5a-j) were synthesized by condensation reaction between 2-amino, 4-substituted phenyl 2-amino thiazole and pyrazine 2-carboxylic acid. These synthesized thiazole derivatives (5a-j) were evaluated for their inhibitory activity against Mycobacterium tuberculosis (Mtb), H37Rv using microplate Alamar Blue assay (MABA). The compound, 5c and 5h showed high anti-mycobacterial activity with MIC value of 6.25 µg/ml, and the compound 5g also exhibited anti-mycobacterial activity with MIC value of 12.50 µg/ml. Molecular docking studies of these synthesized molecules with b-Ketoacyl-ACP Synthase (KasA) protein of Mycobacterium tuberculosis (Mtb) have been carried out to understand the mechanism of anti-mycobacterial action.

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11

Deng, Xinshan, Xiaoyu Tan, Tiantian An, Qingqing Ma, Zhe Jin, Ce Wang, Qingguo Meng, and Chun Hu. "Synthesis, Characterization, and Biological Activity of a Novel Series of Benzo[4,5]imidazo[2,1-b]thiazole Derivatives as Potential Epidermal Growth Factor Receptor Inhibitors." Molecules 24, no. 4 (February 14, 2019): 682. http://dx.doi.org/10.3390/molecules24040682.

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Based on the analysis of epidermal growth factor receptor (EGFR) complexes with gefitinib with molecular docking, the scaffold-hopping strategy, combination of the active substructures, and structural optimization of EGFR inhibitors, a novel series of benzo[4,5]imidazo[2,1-b]thiazole derivatives was designed, synthesized, and evaluated for antitumor activity in human cancer cell lines and cellular toxicity against human normal cell lines using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) colorimetric assay and EGFR inhibitory activities in vitro. Some target compounds such as 2-(benzo[4,5]imidazo[2,1-b]thiazol-3-yl)-N-(2-hydroxyphenyl)acetamide (D04) and 2-(benzo[4,5]imidazo[2,1-b]thiazol-3-yl)-N-(naphthalen-1-yl)acetamide (D08) have shown significant antitumor activity against the EGFR high-expressed human cell line HeLa. All the target compounds showed hardly any antitumor activity against the EGFR low-expressed human cell line HepG2, and nearly no cellular toxicity against the human normal cell lines HL7702 and human umbilical vein endothelial cell lines (HUVEC). The inhibitory activities against EGFR kinase in vitro of the three target compounds were greatly consistent with the anti-proliferative activities. The preliminary structure–activity relationships of the target compounds were summarized. Conclusively, the novel benzo[4,5]imidazo[2,1-b]thiazole derivatives as novel potential EGFR inhibitors may be used as the potential lead compounds for the development of antitumor agents.

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12

Kovtun, Yu P., and N. N. Romanov. "Condensed heterocycles with a thiazole ring. 10. Thiazolo[3,4-b][1,2,4]triazines." Chemistry of Heterocyclic Compounds 21, no. 4 (April 1985): 413–17. http://dx.doi.org/10.1007/bf00504401.

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13

Li, Bing, Xiaodong Shang, Linlin Li, Yuankang Xu, Hanyu Wang, Xiaofeng Yang, Meishan Pei, Ruiqing Zhang, and Guangyou Zhang. "A fluorescence probe based on 6-phenylimidazo[2,1-b]thiazole and salicylaldehyde for the relay discerning of In3+ and Cr3+." New Journal of Chemistry 44, no. 3 (2020): 951–57. http://dx.doi.org/10.1039/c9nj05722f.

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A new fluorescence probe, (E)-N′-(2-hydroxybenzylidene)-6-phenylimidazo[2,1-b]thiazole-3-carbohydrazide (LB1), based on 6-phenylimidazo[2,1-b]thiazole and salicylaldehyde was designed and synthesized.

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14

Sim, Myeonghyeon, Sujin Lee, and Youngtaek Han. "Synthesis and Structural Confirmation of the Thiazole Alkaloids Derived from Peganum harmala L." Applied Sciences 12, no. 1 (December 22, 2021): 78. http://dx.doi.org/10.3390/app12010078.

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Peganumal A and B are thiazole alkaloids isolated from the seeds of Peganum harmala L. Thiazole moieties are rarely found in natural products, but diverse compounds possessing thiazole moieties have attracted attention owing to their broad range of biological activities. Peganumals are the first natural thiazole compounds isolated from the genus Peganum. It was difficult to define the exact structure of peganumal A via spectroscopic analysis. In this paper, we report the first total synthesis of peganumal A and B. The 5-benzylthiazole skeleton possessing methyl or hydrogen at the 2-position of the peganumals was efficiently constructed via the Hantzsch thiazole synthesis of the α-bromoaldehyde intermediate. Moreover, the spectral data of the synthetic 2H–thiazole compound were identical to those previously reported for peganumal A. The synthesis allowed the confirmation of the structure of peganumal A.

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15

Begley, Tadhg P., Steven E. Ealick, and Fred W. McLafferty. "Thiamin biosynthesis: still yielding fascinating biological chemistry." Biochemical Society Transactions 40, no. 3 (May 22, 2012): 555–60. http://dx.doi.org/10.1042/bst20120084.

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The present paper describes the biosynthesis of the thiamin thiazole in Bacillus subtilis and Saccharomyces cerevisiae. The two pathways are quite different: in B. subtilis, the thiazole is formed by an oxidative condensation of glycine, deoxy-D-xylulose 5-phosphate and a protein thiocarboxylate, whereas, in S. cerevisiae, the thiazole is assembled from glycine, NAD and Cys205 of the thiazole synthase.

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16

Bunev, Alexander S., Elena V. Sukhonosova, Vladimir E. Statsyuk, Gennady I. Ostapenko, and Victor N. Khrustalev. "6-(4-Chlorophenyl)-3-methylimidazo[2,1-b]thiazole." Acta Crystallographica Section E Structure Reports Online 69, no. 11 (October 26, 2013): o1701. http://dx.doi.org/10.1107/s1600536813028833.

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In the title compound, C12H9ClN2S, the imidazo[2,1-b]thiazole fragment is planar (r.m.s. deviation = 0.003 Å), and the benzene ring is twisted slightly [by 5.65 (6)°] relative to this moiety. In the crystal, molecules are linked by π–π stacking interactions into columns along [010]. The molecules within the columns are arranged alternatively by their planar rotation of 180°. Thus, in the columns, there are the two types of π–π stacking interactions, namely, (i) between two imidazo[2,1-b]thiazole fragments [interplanar distance = 3.351 (2) Å] and (ii) between an imidazo[2,1-b]thiazole fragment and the phenyl ring [interplanar distance = 3.410 (5) Å]. There are no short contacts between the columns.

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17

Shareef, Mohd Adil, Irfan Khan, Bathini Nagendra Babu, and Ahmed Kamal. "A Comprehensive Review on the Therapeutic Versatility of Imidazo [2,1-b]thiazoles." Current Medicinal Chemistry 27, no. 40 (November 26, 2020): 6864–87. http://dx.doi.org/10.2174/0929867326666190729152440.

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Анотація:

Background:: Imidazo[2,1-b]thiazole, a well-known fused five-membered hetrocycle is one of the most promising and versatile moieties in the area of medicinal chemistry. Derivatives of imidazo[2,1-b]thiazole have been investigated for the development of new derivatives that exhibit diverse pharmacological activities. This fused heterocycle is also a part of a number of therapeutic agents. Objective:: To review the extensive pharmacological activities of imidazo[2,1-b]thiazole derivatives and the new molecules developed between 2000-2018 and their usefulness. Method:: Thorough literature review of all relevant papers and patents was conducted. Conclusion:: The present review, covering a number of aspects, is expected to provide useful insights in the design of imidazo[2,1-b]thiazole-based compounds and would inspire the medicinal chemists for a comprehensive and target-oriented information to achieve a major breakthrough in the development of clinically viable candidates.

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18

Shukla, Upendra K., Raieshwar Singh, J. M. Khanna, Anil K. Saxena, Hemant K. Singh, Ravindra N. Sur, Bhola N. Dhawan, and Nitya Anand. "Synthesis of trans-2-[N-(2-Hydroxy-1,2,3,4-tetrahydronaphthalene-1-yl)]iminothiazolidine and Related Compounds - A New Class of Antidepressants." Collection of Czechoslovak Chemical Communications 57, no. 2 (1992): 415–24. http://dx.doi.org/10.1135/cccc19920415.

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Анотація:

Antiparasitic and antidepressant activities exhibited by tetramisole (I) and its enantiomers prompted the study of its structural analogs trans-2-[N-(2-hydroxy-1,2,3,4-tetrahydronaphthalene/indane-1-yl)]iminothiazolidine (VIII/IX) and 2,3,4a,5,6,10b-hexahydronaphtho[1',2':4,5]-imidazo[2,1-b]thiazole (XII), 2,3,4a,5-tetrahydro-9bH-indeno[1',2':4,5]imidazo[2,1-b]thiazole (XIII), and 2,3,4a,5-tetrahydro-9bH-indeno[1',2':4,5]imidazo[2,1-b]thiazole (XVI), and a homolog 3,4,6,7-tetrahydro-7-phenyl-2H-imidazo[2,1-b]-1,3-thiazine (XX). While none of these compounds showed any noteworthy antiparasitic activity, the trans-2-[N-(2-hydroxy-1,2,3,4-tetrahydronaphthalene-1-yl)]iminothiazolidine (VIII) has shown marked antidepressant activity, better than imipramine in the tests used, and provides a new structural lead for antidepressants.

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19

Abdelrazek, Fathy M., Sobhi M. Gomha, Mohamed E. B. Shaaban, Kamal A. Rabee, Heba N. El-Shemy, Abanoub M. Abdallah, and Peter Metz. "One-Pot Three-Component Synthesis and Molecular Docking of Some Novel 2-Thiazolyl Pyridines as Potent Antimicrobial Agents." Mini-Reviews in Medicinal Chemistry 19, no. 6 (March 7, 2019): 527–38. http://dx.doi.org/10.2174/1389557518666181019124104.

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Background: Thiazoles and pyridines are versatile synthetic scaffolds possessing wide spectrum of biological effects including potential antimicrobial activity. Objective: In the efforts to develop suitable antimicrobia drugs, medicinal chemists have focused on thiazole derivatives. A novel series of 2-thiazolyl pyridines was prepared in a one-pot three-component reaction using 2-bromoacetyl pyridine as a starting precursor. Method: Structure of the synthesized compounds was elucidated by spectral data (FT-IR, 1H NMR, 13C NMR, and mass) and elemental analyses. The prepared compounds were screened for their in vitro antimicrobial activity. Results: The results revealed that compounds 4a,b,e-g and 12 showed promising activity. Molecular docking studies using MOE software were carried out for compounds 4a and 4b which exhibited potent activities indicated by the diameter zones (4a; 3.6, 4.0, 1.2 mm) (4b; 4.2, 3.5, 1.5 mm) and the binding affinities (4a; -5.7731, -5.3576, -4.6844 kcal mol-1) (4b; -5.9356, -2.8250, -5.3628 kcal mol-1) against Candida albicans, Bacillus subtilis and Escherichia coli, respectively. Conclusion: This paper describes a facile and efficient MCR for synthesis of 2-thiazolyl pyridines from reaction of 2-bromoacetyl pyridine with different reagents. There was an agreement between the values of binding affinities and interactions and the data obtained from the practical antimicrobial screening of the tested compounds.

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20

Zukerman-Schpector, J. "A 5,6-dihydroimidazo[2,1-b]thiazole derivative." Acta Crystallographica Section C Crystal Structure Communications 50, no. 12 (December 15, 1994): 2077–79. http://dx.doi.org/10.1107/s010827019400288x.

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21

Leban, I., L. Golič, A. M. Le-Maréchal, and A. Robert. "Structure of 7-(p-tolyl)-2,3-dihydro-5H-thiazolo[4,3-b]thiazole-3,5-dione." Acta Crystallographica Section C Crystal Structure Communications 43, no. 9 (September 15, 1987): 1816–18. http://dx.doi.org/10.1107/s010827018709005x.

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22

Landreau, Cyrille, David Deniaud, Alain Reliquet, and Jean Claude Meslin. "A Facile Access to Imidazo[2,1-b]thiazole and Thiazolo[3,2-a]pyrimidine Derivatives." Synthesis 2001, no. 13 (2001): 2015–20. http://dx.doi.org/10.1055/s-2001-17718.

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23

Kovtun, Yu P., and N. N. Romanov. "Condensed heterocyclic systems with a thiazole ring. 11. Thiazolo [3,4-b]-1,2, 4-triazinones." Chemistry of Heterocyclic Compounds 21, no. 11 (November 1985): 1234–37. http://dx.doi.org/10.1007/bf00515219.

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24

Rashdan, Huda R. M., Aboubakr H. Abdelmonsef, Ihsan A. Shehadi, Sobhi M. Gomha, Abdel Mohsen M. Soliman, and Huda K. Mahmoud. "Synthesis, Molecular Docking Screening and Anti-Proliferative Potency Evaluation of Some New Imidazo[2,1-b]Thiazole Linked Thiadiazole Conjugates." Molecules 25, no. 21 (October 28, 2020): 4997. http://dx.doi.org/10.3390/molecules25214997.

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Background: Imidazo[2,1-b]thiazole scaffolds were reported to possess various pharmaceutical activities. Results: The novel compound named methyl-2-(1-(3-methyl-6-(p-tolyl)imidazo[2,1-b]thiazol-2-yl)ethylidene)hydrazine-1-carbodithioate 3 acted as a predecessor molecule for the synthesis of new thiadiazole derivatives incorporating imidazo[2,1-b]thiazole moiety. The reaction of 3 with the appropriate hydrazonoyl halide derivatives 4a–j and 7–9 had produced the respective 1,3,4-thiadiazole derivatives 6a–j and 10–12. The chemical composition of all the newly synthesized derivatives were confirmed by their microanalytical and spectral data (FT-IR, mass spectrometry, 1H-NMR and 13C-NMR). All the produced novel compounds were screened for their anti-proliferative efficacy on hepatic cancer cell lines (HepG2). In addition, a computational molecular docking study was carried out to determine the ability of the synthesized thiadiazole molecules to interact with active site of the target Glypican-3 protein (GPC-3). Moreover, the physiochemical properties of the synthesized compounds were derived to determine the viability of the compounds as drug candidates for hepatic cancer. Conclusion: All the tested compounds had exhibited good anti-proliferative efficacy against hepatic cancer cell lines. In addition, the molecular docking results showed strong binding interactions of the synthesized compounds with the target GPC-3 protein with lower energy scores. Thus, such novel compounds may act as promising candidates as drugs against hepatocellular carcinoma.

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25

Sonawane, V. D., B. D. Sonawane, M. J. Dhanavade, K. D. Sonawane, and R. B. Bhosale. "Design, Synthesis, Characterization, Anti-Inflammatory and Antioxidant Evaluation of Certain Novel Pyrazoline Derivatives Containing Imidazo[2,1-b]thiazole Moiety." Asian Journal of Organic & Medicinal Chemistry 5, no. 1 (2020): 45–50. http://dx.doi.org/10.14233/ajomc.2020.ajomc-p233.

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In present study, a novel series of substituted imidazo[2,1-b]thiazole pyrazoline derivatives (2a-e) and (3a-e) from the reference compound imidazo[2,1-b]thiazole chalcones (1a-e) in PEG-400 by using hydrazine hydrate and phenyl hydrazine was synthesized. Characterization of newly synthesized compounds was done using IR and 1H NMR. Further, imidazo[2,1-b]thiazole pyrazoline derivatives were subjected to check their in vitro antioxidant activities at a concentration of 0.5 mmol/L in methanol. Compounds 2c, 2d, 3c, 3d and 3e showed comparatively good activity than standard drug diclofenac. The anti-inflammatory activity of compounds 2c, 2d, 2e, 3c, 3d and 3e were comparable with standard drug. Similarly, all these compounds possess good antioxidant activity as compared to ascorbic acid (vitamin C); compared to the value of DPPH and SOD antioxidant activity 44.18 % and 74.07 %, respectively. These synthesized compounds exhibited a good anti-inflammatory and antioxidant activities hence might be useful in future drug designing studies.

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26

Kachkovskii, A. D., Yu P. Kovtun, and N. N. Romanov. "Condensed heterocyclic compounds containing a thiazole ring. 12. Derivatives of thiazolo[3,4-b][1,2,4]triazine." Chemistry of Heterocyclic Compounds 22, no. 12 (December 1986): 1373–76. http://dx.doi.org/10.1007/bf00474364.

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27

Kovtun, Yu P., N. N. Romanov, and A. D. Kachkovskii. "Condensed heterocycles with a thiazole ring. 15. Dyes based on thiazolo[3,4-b][1,2,4]triazine." Chemistry of Heterocyclic Compounds 24, no. 7 (July 1988): 812–18. http://dx.doi.org/10.1007/bf00633183.

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28

Andreani, A., A. Leoni, M. Rambaldi, A. Locatelli, R. Bossa, I. Galatulas, M. Chiericozzi, and M. Bissoli. "Dihydropyridines bearing an imidazo[2,1-b]thiazole system." European Journal of Medicinal Chemistry 32, no. 2 (January 1997): 151–57. http://dx.doi.org/10.1016/s0223-5234(97)87542-3.

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29

Andreani, Aldo, Massimiliano Granaiola, Alberto Leoni, Alessandra Locatelli, Rita Morigi, Mirella Rambaldi, Lucilla Varoli, et al. "Imidazo[2,1-b]thiazole guanylhydrazones as RSK2 inhibitors." European Journal of Medicinal Chemistry 46, no. 9 (September 2011): 4311–23. http://dx.doi.org/10.1016/j.ejmech.2011.07.001.

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30

Grinev, Vyacheslav S., and Alevtina Yu Egorova. "Synthesis of pyrrolo[2,1-b]thiazole derivatives (microreview)." Chemistry of Heterocyclic Compounds 56, no. 2 (February 2020): 164–66. http://dx.doi.org/10.1007/s10593-020-02639-y.

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31

Allard, Nicolas, Nicolas Zindy, Pierre-Olivier Morin, Martijn M. Wienk, René A. J. Janssen, and Mario Leclerc. "Synthesis, characterization and device optimisation of new poly(benzo[1,2-b:4,5-b′]dithiophene-alt-thieno[3,4-d]thiazole) derivatives for solar cell applications." Polymer Chemistry 6, no. 21 (2015): 3956–61. http://dx.doi.org/10.1039/c5py00164a.

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New alternating copolymers based on benzo[1,2-b:4,5-b′]-dithiophene and thieno[3,4-d]thiazole derivatives have been synthesized and their optical, electrochemical and photovoltaic properties were studied.

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32

Zhang, Bao-Le, Li-Xing Song, Ya-Fei Li, Yi-Lei Li, Ya-Zhuo Guo, En Zhang, and Hong-Min Liu. "Synthesis and biological evaluation of dehydroepiandrosterone-fused thiazole, imidazo[2,1-b]thiazole, pyridine steroidal analogues." Steroids 80 (February 2014): 92–101. http://dx.doi.org/10.1016/j.steroids.2013.12.003.

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33

Titus, Sarah, and Kumaran G. Sreejalekshmi. "Propeller-shaped molecules with a thiazole hub: structural landscape and hydrazone cap mediated tunable host behavior in 4-hydrazino-1,3-thiazoles." CrystEngComm 17, no. 31 (2015): 5978–86. http://dx.doi.org/10.1039/c5ce01042j.

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34

Bunev, Alexander S., Elena V. Sukhonosova, Vladimir E. Statsyuk, Gennady I. Ostapenko, and Victor N. Khrustalev. "3-Bromo-2-[4-(methylsulfanyl)phenyl]-5,6,7,8-tetrahydro-1,3-benzothiazolo[3,2-a]imidazole." Acta Crystallographica Section E Structure Reports Online 70, no. 5 (April 26, 2014): o596—o597. http://dx.doi.org/10.1107/s1600536814008976.

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In the title molecule, C16H15BrN2S2, the central imidazo[2,1-b]thiazole fragment is almost planar (r.m.s. deviation = 0.012 Å), and the fused 5,6,7,8-tetrahydrobenzene ring adopts an unsymmetrical half-chair conformation. The dihedral angle between the imidazo[2,1-b]thiazole and benzene planes is 18.25 (4)°. The terminal methylsulfanyl substituent lies practically within the benzene plane [the dihedral angle between the corresponding planes is 7.20 (10)°] and is turned toward the C—Br bond. In the crystal, molecules form infinite chains along [100]viasecondary Br...N interactions [3.1861 (16) Å]. The chains are arranged at van der Waals distances.

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35

Lynch, Daniel E., and Ian McClenaghan. "Ethyl 2-amino-4-tert-butyl-1,3-thiazole-5-carboxylate and 6-methylimidazo[2,1-b]thiazole–2-amino-1,3-thiazole (1/1)." Acta Crystallographica Section C Crystal Structure Communications 60, no. 8 (July 21, 2004): o592—o594. http://dx.doi.org/10.1107/s0108270104015471.

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36

Landreau, Cyrille, David Deniaud, Alain Reliquet, and Jean Claude Meslin. "ChemInform Abstract: A Facile Access to Imidazo[2,1-b]thiazole and Thiazolo[3,2-a]pyrimidine Derivatives." ChemInform 33, no. 6 (May 22, 2010): no. http://dx.doi.org/10.1002/chin.200206138.

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37

Yin, Xin-ying, Zhi-yu Yang, Guo-li Huang, Jian-jian Bian, Deng-qiang Wang, Qin Wang, Ming-yu Teng, Zheng-liang Wang, and Jie Zhang. "Synthesis and properties of a series of iridium complexes with imidazolo[2,1-b]thiazole derivatives as primary ligands." New Journal of Chemistry 43, no. 15 (2019): 5849–56. http://dx.doi.org/10.1039/c8nj06295a.

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38

Moody, Christopher J., and James C. A. Hunt. "Synthesis of Virenamide B, a Cytotoxic Thiazole-Containing Peptide." Journal of Organic Chemistry 64, no. 23 (November 1999): 8715–17. http://dx.doi.org/10.1021/jo9908694.

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39

Andreani, Aldo, Silvia Burnelli, Massimiliano Granaiola, Alberto Leoni, Alessandra Locatelli, Rita Morigi, Mirella Rambaldi, et al. "New Antitumor Imidazo[2,1-b]thiazole Guanylhydrazones and Analogues1." Journal of Medicinal Chemistry 51, no. 4 (February 2008): 809–16. http://dx.doi.org/10.1021/jm701246g.

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40

Balwe, Sandip Gangadhar, and Yeon Tae Jeong. "Iron-catalyzed unprecedented formation of benzo[d]imidazo[2,1-b]thiazoles under solvent-free conditions." RSC Advances 6, no. 109 (2016): 107225–32. http://dx.doi.org/10.1039/c6ra24183b.

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41

Alsayari, Abdulrhman, Abdullatif Bin Muhsinah, Yahya I. Asiri, Faiz A. Al-aizari, Nabila A. Kheder, Zainab M. Almarhoon, Hazem A. Ghabbour, and Yahia N. Mabkhot. "Synthesis, Characterization, and Biological Evaluation of Some Novel Pyrazolo[5,1-b]thiazole Derivatives as Potential Antimicrobial and Anticancer Agents." Molecules 26, no. 17 (September 4, 2021): 5383. http://dx.doi.org/10.3390/molecules26175383.

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The pharmacological activities of thiazole and pyrazole moieties as antimicrobial and anticancer agents have been thoroughly described in many literature reviews. In this study, a convenient synthesis of novel pyrazolo[5,1-b]thiazole-based heterocycles was carried out. The synthesized compounds were characterized by IR, 1H and 13C NMR spectroscopy and mass spectrometry. Some selected examples were screened and evaluated for their antimicrobial and anticancer activities and showed promising results. These products could serve as leading compounds in the future design of new drug molecules.

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42

Elnaggar, Dina H., Naglaa A. Abdel Hafez, Huda R. M. Rashdan, Nayera A. M. Abdelwahed, Hanem M. Awad, and Korany A. Ali. "Synthesis, Antimicrobial and Antitumor Evaluations of a New Class of Thiazoles Substituted on the Chromene Scaffold." Mini-Reviews in Medicinal Chemistry 19, no. 20 (December 16, 2019): 1717–25. http://dx.doi.org/10.2174/1389557519666190722123422.

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Background & Objective: A new series of thiazoles substituted on the chromene scaffold were prepared by facial approaches starting from (E)-1-(2,3-Dihydrochromen-4-ylidene)thiosemicarbazide derivatives (2a,b). The thiosemicarbazides (2a,b) were reacted with a series of α-halo carbonyl compounds to give the corresponding rhodanine analogues and reacted also with C-acetyl-or Cethoxy- N-hydrazonoyl chlorides to afford the corresponding tri- and tetra-substituted hybrid hydrazinyl thiazole substituted chromenes. Methods: The newly synthesized compounds were screened for their in vitro antimicrobial and antitumor activities by agar diffusion method and MTT assay, respectively. Results: The results of the antimicrobial activity revealed that some of the new compounds exhibited excellent activity against pathogenic microorganism; Candida albicans compared with Ciprofloxacin and nystatin, as the reference drugs. : All of the tested compounds exhibited significant cytotoxic activities comparable to that of the reference drug; Doxorubicin® (on HCT116 (colorectal carcinoma human cell line).

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43

Foize Ahmad, G., A. Syed Mohammed Mujaheer, M. NizamMohideen, M. Gulam Mohamed, and V. Viswanathan. "The crystal structures and Hirshfeld surface analysis of 6-(naphthalen-1-yl)-6a-nitro-6,6a,6b,7,9,11a-hexahydrospiro[chromeno[3′,4′:3,4]pyrrolo[1,2-c]thiazole-11,11′-indeno[1,2-b]quinoxaline] and 6′-(naphthalen-1-yl)-6a′-nitro-6′,6a′,6b′,7′,8′,9′,10′,12a′-octahydro-2H-spiro[acenaphthylene-1,12′-chromeno[3,4-a]indolizin]-2-one." Acta Crystallographica Section E Crystallographic Communications 75, no. 10 (September 27, 2019): 1519–24. http://dx.doi.org/10.1107/s205698901901291x.

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The title compounds, 6-(naphthalen-1-yl)-6a-nitro-6,6a,6 b,7,9,11a-hexahydrospiro[chromeno[3′,4′:3,4]pyrrolo[1,2-c]thiazole-11,11′-indeno[1,2-b]quinoxaline], C37H26N4O3S, (I), and 6′-(naphthalen-1-yl)-6a′-nitro-6′,6a′,6b′,7′,8′,9′,10′,12a′-octahydro-2H-spiro[acenaphthylene-1,12′-chromeno[3,4-a]indolizin]-2-one, C36H28N2O4, (II), are new spiro derivatives, in which both the pyrrolidine rings adopt twisted conformations. In (I), the five-membered thiazole ring adopts an envelope conformation, while the eight-membered pyrrolidine-thiazole ring adopts a boat conformation. An intramolecular C—H...N hydrogen bond occurs, involving a C atom of the pyran ring and an N atom of the pyrazine ring. In (II), the six-membered piperidine ring adopts a chair conformation. An intramolecular C—H...O hydrogen bond occurs, involving a C atom of the pyrrolidine ring and the keto O atom. For both compounds, the crystal structure is stabilized by intermolecular C—H...O hydrogen bonds. In (I), the C—H...O hydrogen bonds link adjacent molecules, forming R 2 2(16) loops propagating along the b-axis direction, while in (II) they form zigzag chains along the b-axis direction. In both compounds, C—H...π interactions help to consolidate the structure, but no significant π–π interactions with centroid–centroid distances of less than 4 Å are observed.

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44

Sachdeva, Harshita, Diksha Dwivedi, R. R. Bhattacharjee, Sarita Khaturia, and Rekha Saroj. "NiO Nanoparticles: An Efficient Catalyst for the Multicomponent One-Pot Synthesis of Novel Spiro and Condensed Indole Derivatives." Journal of Chemistry 2013 (2013): 1–10. http://dx.doi.org/10.1155/2013/606259.

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An efficient catalytic protocol for the synthesis of novel spiro[indoline-3,4′-pyrano[2,3-c]thiazole]carbonitriles and condensed thiazolo[5′′,4′′:5′,6′]pyrano[4′,3′:3,4]furo[2,3-b]indole derivatives is developed in a one-pot three-component approach involving substituted 1H-indole-2,3-diones, activated methylene reagent, and 2-thioxo-4-thiazolidinone under conventional heating and microwave irradiation. This paper describes the use of NiO nanoparticles as catalyst for the synthesis of novel spiro and condensed indole derivatives by Knoevenagel condensation followed by Michael addition. The advantageous features of this methodology are operational simplicity, high yield processing, and easy handling. The particle size of NiO nanoparticle was determined by XRD. After reaction course, NiO nanoparticles can be recycled and reused without any apparent loss of activity.

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45

Ramprasad, Jurupula, Nagabhushana Nayak, Udayakumar Dalimba, Perumal Yogeeswari, and Dharmarajan Sriram. "Ionic liquid-promoted one-pot synthesis of thiazole–imidazo[2,1-b][1,3,4]thiadiazole hybrids and their antitubercular activity." MedChemComm 7, no. 2 (2016): 338–44. http://dx.doi.org/10.1039/c5md00346f.

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46

Hédou, Damien, Emmanuel Deau, Marine Harari, Morgane Sanselme, Corinne Fruit, and Thierry Besson. "Rational multistep synthesis of a novel polyfunctionalized benzo[d]thiazole and its thiazolo[5,4-b]pyridine analogue." Tetrahedron 70, no. 35 (September 2014): 5541–49. http://dx.doi.org/10.1016/j.tet.2014.06.103.

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47

Ghabbour, Hazem A., Adnan A. Kadi, Hussein I. El-Subbagh, Tze Shyang Chia, and Hoong-Kun Fun. "1-(5-Bromo-4-phenyl-1,3-thiazol-2-yl)pyrrolidin-2-one." Acta Crystallographica Section E Structure Reports Online 68, no. 6 (May 16, 2012): o1738—o1739. http://dx.doi.org/10.1107/s160053681201954x.

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The asymmetric unit of the title compound, C13H11BrN2OS, consists of two crystallographically independent molecules (A and B). In each molecule, the pyrrolidine ring adopts an envelope conformation with a methylene C atom as the flap atom. In molecule A, the central thiazole ring makes a dihedral angle of 36.69 (11)° with the adjacent phenyl ring, whereas the corresponding angle is 36.85 (12)° in molecule B. The pyrrolidine ring is slightly twisted from the thiazole ring, with C—N—C—N torsion angles of 4.8 (3) and 3.0 (4)° in molecules A and B, respectively. In the crystal, C—H...π and π–π [centroid-to-centroid distance = 3.7539 (14) Å] interactions are observed. The crystal studied was a pseudo-merohedral twin with twin law (-100 0-10 101) and a refined component ratio of 0.7188 (5):0.2812 (5).

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48

Shareef, Mohd Adil, Ganthala Parimala Devi, Sunitha Rani Routhu, C. Ganesh Kumar, Ahmed Kamal, and Bathini Nagendra Babu. "New imidazo[2,1-b]thiazole-based aryl hydrazones: unravelling their synthesis and antiproliferative and apoptosis-inducing potential." RSC Medicinal Chemistry 11, no. 10 (2020): 1178–84. http://dx.doi.org/10.1039/d0md00188k.

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49

Ali, Esraa M., Ahmed W. Naser, and Muthanna S. Farhan. "SYNTHESIS OF SOME NEW HETEROCYCLIC COMPOUNDS DERIVED FROM N-(Ñ-PHENYL GLYCYL) SACCHARIN AND STUDY THEIR BIOLOGICAL ACTIVITY." Asian Journal of Pharmaceutical and Clinical Research 11, no. 10 (October 7, 2018): 555. http://dx.doi.org/10.22159/ajpcr.2018.v11i10.29048.

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Objective: In the present work, a variety of new heterocyclic compounds namely aza-β- lactam, cyclicimides, 1,3-thiazole, and 1,2,4-triazole.Methods: Procedure includes the synthesis of aza-β- lactam, cyclic imides, 1,3-thiazole, and 1,2,4-triazole. The synthesis was carried out in eleven steps using N-(Ñ-substituted phenylglycyl) saccharin derivatives (1a,b) as a starting material and converted to benzoic acid derivatives (2a,b) and then to ester derivatives (3a,b), which finally convers to benzohydrazide derivatives (4a,b). The cyclization of (4a,b) with carbon disulfide and hydrazine hydrate (80%) in the presence of potassium hydroxide gives 1,2,4-triazole compounds (5a,b), and subsequently (5a,b) derivatives reacted with different aromatic aldehydes in the presence of few drops of glacial acetic acid to give Schiff bases (6a-f). Compounds (7a-b) was prepared by the reaction of compounds (4a,b) with chloroacetyl chloride. 1,3-thiazole derivatives (8a,b) were synthesized through the cyclization of compounds (7a,b) with thiourea. Schiff bases (9a-f) were obtained by condensation of (4a,b) with different aromatic aldehydes in the presence of few drops of glacial acetic acid. Aza-β-lactam compounds (10a-f) were prepared by the cycloaddition of Schiff-bases (9a-f) with phenyl isocyanate through [2+2] cycloaddition reaction. Reaction (4a,b) with various acid anhydrides in presence of acetic acid gave the corresponding cyclic imide (11a-f). The newly prepared.Results: The results showed that compounds (5a) and (10e) have a good activity against Gram-positive bacterium and no activity against Gram-negative bacterium, compared to standard drugs (ciprofloxacin and amoxicillin), while compounds (8a) and (6b) have a high activity against fungi, compared to standard drugs (metronidazole benzoate), and the other tested compounds have low-to-moderate activity.Conclusion: 1,2,4-triazole is a most potent assemblage of Gram-positive bacterium retardants and cyclic imides are a most potent assemblage of fungi retardants.

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50

Journal, Baghdad Science. "Synthesis of some Heterocyclic Compounds Derived from." Baghdad Science Journal 10, no. 3 (September 1, 2013): 525–36. http://dx.doi.org/10.21123/bsj.10.3.525-536.

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The 4-(?-bromo acetyl)-4?-toluene sulfonanilide (2) was used as key intermediate to synthesize new heterocyclic compounds. This bromo compound was synthesized via sulfonation of amino group of p-amino acetophenone using Hinsburg method with 4-toluene sulfonyl chloride to form 4-acetyl-4?-toluene sulfonanilide (1) which is used as a starting material in this work. This compound was brominated to yield compound (2) which is used as a precursor to synthesize new five and seven membered heterocyclic compounds such as substituted 1,3-oxazoles (3,4), 1,3-thiazole derivatives (5-7), thiourea compounds (8a,b), 1,3-Thiazoline-2-thione compounds (9a-f) and 1,2,5-triazepine compounds (11a-d). The synthesized compounds were identified depending upon physical, FT-IR and UV spectroscopic data.

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