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Schiff bases and their amines: Synthesis and discovery of carbonic anhydrase and acetylcholinesterase enzymes inhibitors.
Arch Pharm (Weinheim). 2018 Sep; 351(9):e1800146.AP

Abstract

Three series of symmetrical Schiff bases were synthesized from 1,2-diaminoethane, 1,3-diaminopropane and 1,4-diaminobutane and substituted benzaldehydes, and reduced by sodium borohydride to the corresponding benzylic diamines 4-6. All of the compounds obtained were characterized using elemental analysis, FT-IR, 1 H NMR, and 13 C NMR spectroscopy. The enzyme inhibitory properties of these compounds were tested and the influence of the alkane chain length and the substituents on the phenyl group on the enzyme inhibition activity were examined. The novel Schiff bases and their amine derivatives (1a-d, 2a-d, 3b-d, 4a-c, 5a-c, 6a, 6c, 6d) were effective inhibitors of the cytosolic carbonic anhydrase I and II isoforms (hCA I and II), and acetylcholinesterase (AChE) with Ki values in the range of 159.43 ± 30.03 to 563.73 ± 115.30 nM for hCA I, 104.88 ± 18.44 to 524.32 ± 95.03 nM for hCA II, and 3.95 ± 0.74 to 30.83 ± 6.81 nM for AChE.

Authors+Show Affiliations

Faculty of Science and Art, Department of Chemistry, Adıyaman University, Adıyaman, Turkey.Faculty of Science and Art, Department of Chemistry, Adıyaman University, Adıyaman, Turkey.Faculty of Science, Department of Chemistry, Atatürk University, Erzurum, Turkey.Faculty of Science and Art, Department of Chemistry, Inönü University, Malatya, Turkey.Faculty of Science, Department of Chemistry, Atatürk University, Erzurum, Turkey.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

30033646

Citation

Yiğit, Beyhan, et al. "Schiff Bases and Their Amines: Synthesis and Discovery of Carbonic Anhydrase and Acetylcholinesterase Enzymes Inhibitors." Archiv Der Pharmazie, vol. 351, no. 9, 2018, pp. e1800146.
Yiğit B, Yiğit M, Taslimi P, et al. Schiff bases and their amines: Synthesis and discovery of carbonic anhydrase and acetylcholinesterase enzymes inhibitors. Arch Pharm (Weinheim). 2018;351(9):e1800146.
Yiğit, B., Yiğit, M., Taslimi, P., Gök, Y., & Gülçin, İ. (2018). Schiff bases and their amines: Synthesis and discovery of carbonic anhydrase and acetylcholinesterase enzymes inhibitors. Archiv Der Pharmazie, 351(9), e1800146. https://doi.org/10.1002/ardp.201800146
Yiğit B, et al. Schiff Bases and Their Amines: Synthesis and Discovery of Carbonic Anhydrase and Acetylcholinesterase Enzymes Inhibitors. Arch Pharm (Weinheim). 2018;351(9):e1800146. PubMed PMID: 30033646.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Schiff bases and their amines: Synthesis and discovery of carbonic anhydrase and acetylcholinesterase enzymes inhibitors. AU - Yiğit,Beyhan, AU - Yiğit,Murat, AU - Taslimi,Parham, AU - Gök,Yetkin, AU - Gülçin,İlhami, Y1 - 2018/07/22/ PY - 2018/05/14/received PY - 2018/06/20/revised PY - 2018/06/29/accepted PY - 2018/7/24/pubmed PY - 2018/12/12/medline PY - 2018/7/24/entrez KW - 1,2-diaminoethane KW - 1,3-diaminopropane KW - Schiff bases KW - acetylcholinesterase KW - carbonic anhydrase KW - enzyme inhibition SP - e1800146 EP - e1800146 JF - Archiv der Pharmazie JO - Arch. Pharm. (Weinheim) VL - 351 IS - 9 N2 - Three series of symmetrical Schiff bases were synthesized from 1,2-diaminoethane, 1,3-diaminopropane and 1,4-diaminobutane and substituted benzaldehydes, and reduced by sodium borohydride to the corresponding benzylic diamines 4-6. All of the compounds obtained were characterized using elemental analysis, FT-IR, 1 H NMR, and 13 C NMR spectroscopy. The enzyme inhibitory properties of these compounds were tested and the influence of the alkane chain length and the substituents on the phenyl group on the enzyme inhibition activity were examined. The novel Schiff bases and their amine derivatives (1a-d, 2a-d, 3b-d, 4a-c, 5a-c, 6a, 6c, 6d) were effective inhibitors of the cytosolic carbonic anhydrase I and II isoforms (hCA I and II), and acetylcholinesterase (AChE) with Ki values in the range of 159.43 ± 30.03 to 563.73 ± 115.30 nM for hCA I, 104.88 ± 18.44 to 524.32 ± 95.03 nM for hCA II, and 3.95 ± 0.74 to 30.83 ± 6.81 nM for AChE. SN - 1521-4184 UR - https://www.unboundmedicine.com/medline/citation/30033646/Schiff_bases_and_their_amines:_Synthesis_and_discovery_of_carbonic_anhydrase_and_acetylcholinesterase_enzymes_inhibitors_ L2 - https://doi.org/10.1002/ardp.201800146 DB - PRIME DP - Unbound Medicine ER -