S-Alkylated/aralkylated 2-(1H-indol-3-yl-methyl)-1,3,4- oxadiazole-5-thiol derivatives. 1. Synthesis and Characterization
Purpose: To synthesize and characterize S-alkylated/aralkylated 2-(1H-indol-3-ylmethyl)-1,3,4- oxadiazole-5-thiol derivatives. Methods: 2-(1H-indol-3-yl)acetic acid (1) was reacted with absolute ethanol and catalytic amount of sulfuric acid to form ethyl 2-(1H-indol-3-yl)acetate (2) which was transf...
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Pharmacotherapy Group
2016
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| Online Access: | http://umpir.ump.edu.my/id/eprint/16812/ http://umpir.ump.edu.my/id/eprint/16812/1/fist-2016-nadeem-S-Alkylatedaralkylated%202-%281H-indol-3-yl-methyl%29-1%2C3%2C44.pdf |
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| author | Rubab, Kaniz Abbasi, Muhammad A. Rehman, Aziz-ur Siddiqui, Sabahat Zahra Akhtar, Muhammad Nadeem |
| author_facet | Rubab, Kaniz Abbasi, Muhammad A. Rehman, Aziz-ur Siddiqui, Sabahat Zahra Akhtar, Muhammad Nadeem |
| author_sort | Rubab, Kaniz |
| building | UMP Institutional Repository |
| collection | Online Access |
| description | Purpose: To synthesize and characterize S-alkylated/aralkylated 2-(1H-indol-3-ylmethyl)-1,3,4- oxadiazole-5-thiol derivatives. Methods: 2-(1H-indol-3-yl)acetic acid (1) was reacted with absolute ethanol and catalytic amount of sulfuric acid to form ethyl 2-(1H-indol-3-yl)acetate (2) which was transformed to 2-(1H-indol-3- yl)acetohydrazide (3) by refluxing with hydrazine hydrate in methanol. Ring closure reaction of 3 with carbon disulfide and ethanolic potassium hydroxide yielded 2-(1H-indol-3-ylmethyl)-1,3,4-oxadiazole-5- thiol (4) which was finally treated with alkyl/aralkyl halides (5a-u) in DMF and NaH to yield Salkylated/ aralkylated 2-(1H-indol-3-ylmethyl)-1,3,4-oxadiazole-5-thiols (6a-u). Structural elucidation was done by IR, 1H-NMR and EI-MS techniques
Results: 2-(1H-indol-3-ylmethyl)-1,3,4-oxadiazole-5-thiol (4) was synthesized as the parent molecule and was characterized by IR and the spectrum showed peaks resonating at (cm-1) 2925 (Ar-H), 2250 (S-H ), 1593 (C=N ) and 1527 (Ar C=C ); 1H-NMR spectrum showed signals at δ 11.00 (s, 1H, NH-1ʹ), 7.49 ( br.d, J = 7.6 Hz, 1H, H-4'), 7.37 (br.d, J = 8.0 Hz, 1H, H-7'), 7.34 (br.s, 1H, H-2'), 7.09 (t, J = 7.6Hz, 1H, H-5'), 7.00 (t, J = 7.6 Hz, 1H, H-6') and 4.20 (s, 2H, CH2-10ʹ). EI-MS presented different fragments peaks at m/z 233 (C11H9N3OS)˙+ [M+2]+, 231 (C11H9N3OS)˙+ [M]+, 158 (C10H8NO)+, 156 (C10H8N2)˙+, 130 (C9H8N)+. The derivatives (6a-6u) were prepared and characterized accordingly. Conclusion: S-alkylated/aralkylated 2-(1H-indol-3-ylmethyl)-1,3,4-oxadiazole-5-thiols (6a-u) were successfully synthesized. |
| first_indexed | 2025-11-15T02:06:56Z |
| format | Article |
| id | ump-16812 |
| institution | Universiti Malaysia Pahang |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-15T02:06:56Z |
| publishDate | 2016 |
| publisher | Pharmacotherapy Group |
| recordtype | eprints |
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| spelling | ump-168122018-04-19T02:35:42Z http://umpir.ump.edu.my/id/eprint/16812/ S-Alkylated/aralkylated 2-(1H-indol-3-yl-methyl)-1,3,4- oxadiazole-5-thiol derivatives. 1. Synthesis and Characterization Rubab, Kaniz Abbasi, Muhammad A. Rehman, Aziz-ur Siddiqui, Sabahat Zahra Akhtar, Muhammad Nadeem QR Microbiology Purpose: To synthesize and characterize S-alkylated/aralkylated 2-(1H-indol-3-ylmethyl)-1,3,4- oxadiazole-5-thiol derivatives. Methods: 2-(1H-indol-3-yl)acetic acid (1) was reacted with absolute ethanol and catalytic amount of sulfuric acid to form ethyl 2-(1H-indol-3-yl)acetate (2) which was transformed to 2-(1H-indol-3- yl)acetohydrazide (3) by refluxing with hydrazine hydrate in methanol. Ring closure reaction of 3 with carbon disulfide and ethanolic potassium hydroxide yielded 2-(1H-indol-3-ylmethyl)-1,3,4-oxadiazole-5- thiol (4) which was finally treated with alkyl/aralkyl halides (5a-u) in DMF and NaH to yield Salkylated/ aralkylated 2-(1H-indol-3-ylmethyl)-1,3,4-oxadiazole-5-thiols (6a-u). Structural elucidation was done by IR, 1H-NMR and EI-MS techniques Results: 2-(1H-indol-3-ylmethyl)-1,3,4-oxadiazole-5-thiol (4) was synthesized as the parent molecule and was characterized by IR and the spectrum showed peaks resonating at (cm-1) 2925 (Ar-H), 2250 (S-H ), 1593 (C=N ) and 1527 (Ar C=C ); 1H-NMR spectrum showed signals at δ 11.00 (s, 1H, NH-1ʹ), 7.49 ( br.d, J = 7.6 Hz, 1H, H-4'), 7.37 (br.d, J = 8.0 Hz, 1H, H-7'), 7.34 (br.s, 1H, H-2'), 7.09 (t, J = 7.6Hz, 1H, H-5'), 7.00 (t, J = 7.6 Hz, 1H, H-6') and 4.20 (s, 2H, CH2-10ʹ). EI-MS presented different fragments peaks at m/z 233 (C11H9N3OS)˙+ [M+2]+, 231 (C11H9N3OS)˙+ [M]+, 158 (C10H8NO)+, 156 (C10H8N2)˙+, 130 (C9H8N)+. The derivatives (6a-6u) were prepared and characterized accordingly. Conclusion: S-alkylated/aralkylated 2-(1H-indol-3-ylmethyl)-1,3,4-oxadiazole-5-thiols (6a-u) were successfully synthesized. Pharmacotherapy Group 2016 Article PeerReviewed application/pdf en http://umpir.ump.edu.my/id/eprint/16812/1/fist-2016-nadeem-S-Alkylatedaralkylated%202-%281H-indol-3-yl-methyl%29-1%2C3%2C44.pdf Rubab, Kaniz and Abbasi, Muhammad A. and Rehman, Aziz-ur and Siddiqui, Sabahat Zahra and Akhtar, Muhammad Nadeem (2016) S-Alkylated/aralkylated 2-(1H-indol-3-yl-methyl)-1,3,4- oxadiazole-5-thiol derivatives. 1. Synthesis and Characterization. Tropical Journal of Pharmaceutical Research, 15 (7). pp. 1515-1524. ISSN 1596-5996 (print); 1596-9827 (online). (Published) http://dx.doi.org/10.4314/tjpr.v15i7.23 doi: 10.4314/tjpr.v15i7.23 |
| spellingShingle | QR Microbiology Rubab, Kaniz Abbasi, Muhammad A. Rehman, Aziz-ur Siddiqui, Sabahat Zahra Akhtar, Muhammad Nadeem S-Alkylated/aralkylated 2-(1H-indol-3-yl-methyl)-1,3,4- oxadiazole-5-thiol derivatives. 1. Synthesis and Characterization |
| title | S-Alkylated/aralkylated 2-(1H-indol-3-yl-methyl)-1,3,4- oxadiazole-5-thiol derivatives. 1. Synthesis and Characterization |
| title_full | S-Alkylated/aralkylated 2-(1H-indol-3-yl-methyl)-1,3,4- oxadiazole-5-thiol derivatives. 1. Synthesis and Characterization |
| title_fullStr | S-Alkylated/aralkylated 2-(1H-indol-3-yl-methyl)-1,3,4- oxadiazole-5-thiol derivatives. 1. Synthesis and Characterization |
| title_full_unstemmed | S-Alkylated/aralkylated 2-(1H-indol-3-yl-methyl)-1,3,4- oxadiazole-5-thiol derivatives. 1. Synthesis and Characterization |
| title_short | S-Alkylated/aralkylated 2-(1H-indol-3-yl-methyl)-1,3,4- oxadiazole-5-thiol derivatives. 1. Synthesis and Characterization |
| title_sort | s-alkylated/aralkylated 2-(1h-indol-3-yl-methyl)-1,3,4- oxadiazole-5-thiol derivatives. 1. synthesis and characterization |
| topic | QR Microbiology |
| url | http://umpir.ump.edu.my/id/eprint/16812/ http://umpir.ump.edu.my/id/eprint/16812/ http://umpir.ump.edu.my/id/eprint/16812/ http://umpir.ump.edu.my/id/eprint/16812/1/fist-2016-nadeem-S-Alkylatedaralkylated%202-%281H-indol-3-yl-methyl%29-1%2C3%2C44.pdf |