Synthesis and Characterization of New 2-amino-5-chlorobenzothiazole Derivatives Containing Different Types of Heterocyclic as Antifungal Activity
Nine new compounds of 2-amino-5-chlorobenzothiazole derivatives were synthesized. These new compounds were formed through the reaction of 2-amino-5-chlorobenzothiazole 1 with ethyl chloroacetate and KOH, which gave an ester derivative 2, followed by refluxing compound 2 with hydrazine hydrate to af...
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University of Baghdad, College of Science for Women
2024-03-01
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| Series: | مجلة بغداد للعلوم |
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| Online Access: | https://bsj.uobaghdad.edu.iq/index.php/BSJ/article/view/8318 |
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| author | Shaima Ibraheem Chyad AL-Khazraji Wafa Mohammad Sadik Luma S. Ahamed |
| author_facet | Shaima Ibraheem Chyad AL-Khazraji Wafa Mohammad Sadik Luma S. Ahamed |
| author_sort | Shaima Ibraheem Chyad AL-Khazraji |
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Nine new compounds of 2-amino-5-chlorobenzothiazole derivatives were synthesized. These new compounds were formed through the reaction of 2-amino-5-chlorobenzothiazole 1 with ethyl chloroacetate and KOH, which gave an ester derivative 2, followed by refluxing compound 2 with hydrazine hydrate to afford hydrazide derivative 3. The reaction of compound 3 with CS2 and KOH gave 1,3,4-oxadiazole-2-thiol derivative 4, and then the reaction of compound 2 with thiosemicarbazide to produce compound 5 then treated it with 4%NaOH led to ring closure to provide 1,2,4-triazole-3-thiol derivative 6. The reaction of 2-amino-5-chlorobenzothiazole1 with chloroacetic acid gave 7 followed by refluxing the latter compound with ortho amino aniline giving benzimidazole derivative 8. Azomethine 9 was synthesized over 2-amino-6-chloro-benzothiazole with bromobenzaldehyde, the last compound 9 was converted to a thiazolidinone derivative 10 through the reaction of compound 9 with 2-mercaptoaceticacid. The prepared derivatives were established by using FT-IR, 1H-NMR spectroscopy, elemental analysis C.H.N. and physical properties. Entirely compounds were examined for their anti-fungal action against Candida glabrata and Aspergillus niger, and the results revealed that some compounds showed a good measurable activity comparing with fluconazole as stander drug.
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| format | Article |
| id | doaj-art-177a943a1a0f45499ea256bcb90a58a4 |
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| issn | 2078-8665 2411-7986 |
| language | English |
| publishDate | 2024-03-01 |
| publisher | University of Baghdad, College of Science for Women |
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| series | مجلة بغداد للعلوم |
| spelling | doaj-art-177a943a1a0f45499ea256bcb90a58a42025-08-20T02:53:07ZengUniversity of Baghdad, College of Science for Womenمجلة بغداد للعلوم2078-86652411-79862024-03-0121310.21123/bsj.2023.8318Synthesis and Characterization of New 2-amino-5-chlorobenzothiazole Derivatives Containing Different Types of Heterocyclic as Antifungal ActivityShaima Ibraheem Chyad AL-Khazraji0https://orcid.org/0000-0002-3655-0712Wafa Mohammad Sadik1https://orcid.org/0000-0003-0614-3793Luma S. Ahamed 2https://orcid.org/0000-0002-6482-6747Department of Chemistry, College of Education for Pure Sciences, University of Kirkuk, Kirkuk, Iraq.Department of Chemistry, College of Education for Pure Sciences, University of Kirkuk, Kirkuk, Iraq.Department of Chemistry, College of Science, University of Baghdad, Baghdad, Iraq. Nine new compounds of 2-amino-5-chlorobenzothiazole derivatives were synthesized. These new compounds were formed through the reaction of 2-amino-5-chlorobenzothiazole 1 with ethyl chloroacetate and KOH, which gave an ester derivative 2, followed by refluxing compound 2 with hydrazine hydrate to afford hydrazide derivative 3. The reaction of compound 3 with CS2 and KOH gave 1,3,4-oxadiazole-2-thiol derivative 4, and then the reaction of compound 2 with thiosemicarbazide to produce compound 5 then treated it with 4%NaOH led to ring closure to provide 1,2,4-triazole-3-thiol derivative 6. The reaction of 2-amino-5-chlorobenzothiazole1 with chloroacetic acid gave 7 followed by refluxing the latter compound with ortho amino aniline giving benzimidazole derivative 8. Azomethine 9 was synthesized over 2-amino-6-chloro-benzothiazole with bromobenzaldehyde, the last compound 9 was converted to a thiazolidinone derivative 10 through the reaction of compound 9 with 2-mercaptoaceticacid. The prepared derivatives were established by using FT-IR, 1H-NMR spectroscopy, elemental analysis C.H.N. and physical properties. Entirely compounds were examined for their anti-fungal action against Candida glabrata and Aspergillus niger, and the results revealed that some compounds showed a good measurable activity comparing with fluconazole as stander drug. https://bsj.uobaghdad.edu.iq/index.php/BSJ/article/view/83182-amino-5-chlorobenzothiazol, anti-fungal, benzimidazole, oxadiazole, thiazolidine-4-one, triazole |
| spellingShingle | Shaima Ibraheem Chyad AL-Khazraji Wafa Mohammad Sadik Luma S. Ahamed Synthesis and Characterization of New 2-amino-5-chlorobenzothiazole Derivatives Containing Different Types of Heterocyclic as Antifungal Activity مجلة بغداد للعلوم 2-amino-5-chlorobenzothiazol, anti-fungal, benzimidazole, oxadiazole, thiazolidine-4-one, triazole |
| title | Synthesis and Characterization of New 2-amino-5-chlorobenzothiazole Derivatives Containing Different Types of Heterocyclic as Antifungal Activity |
| title_full | Synthesis and Characterization of New 2-amino-5-chlorobenzothiazole Derivatives Containing Different Types of Heterocyclic as Antifungal Activity |
| title_fullStr | Synthesis and Characterization of New 2-amino-5-chlorobenzothiazole Derivatives Containing Different Types of Heterocyclic as Antifungal Activity |
| title_full_unstemmed | Synthesis and Characterization of New 2-amino-5-chlorobenzothiazole Derivatives Containing Different Types of Heterocyclic as Antifungal Activity |
| title_short | Synthesis and Characterization of New 2-amino-5-chlorobenzothiazole Derivatives Containing Different Types of Heterocyclic as Antifungal Activity |
| title_sort | synthesis and characterization of new 2 amino 5 chlorobenzothiazole derivatives containing different types of heterocyclic as antifungal activity |
| topic | 2-amino-5-chlorobenzothiazol, anti-fungal, benzimidazole, oxadiazole, thiazolidine-4-one, triazole |
| url | https://bsj.uobaghdad.edu.iq/index.php/BSJ/article/view/8318 |
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