PreprintArticleVersion 1This version is not peer-reviewed
An Insight into the Anticancer and Antibacterial Properties of New 4-(Benzylamino)benzoic Acid Derivatives: Synthesis and X-ray Crystallographic Analysis
Version 1
: Received: 25 September 2024 / Approved: 26 September 2024 / Online: 26 September 2024 (09:15:01 CEST)
How to cite:
Hijazi, A. K.; Sarayrah, Q. M.; Malkawi, A. W.; Abul-Futouh, H.; Taha, Z. A.; Abusara, O. H.; Daraosheh, A. Q.; Ahmad, A. A. L.; Nureldeen, W. An Insight into the Anticancer and Antibacterial Properties of New 4-(Benzylamino)benzoic Acid Derivatives: Synthesis and X-ray Crystallographic Analysis. Preprints2024, 2024092060. https://doi.org/10.20944/preprints202409.2060.v1
Hijazi, A. K.; Sarayrah, Q. M.; Malkawi, A. W.; Abul-Futouh, H.; Taha, Z. A.; Abusara, O. H.; Daraosheh, A. Q.; Ahmad, A. A. L.; Nureldeen, W. An Insight into the Anticancer and Antibacterial Properties of New 4-(Benzylamino)benzoic Acid Derivatives: Synthesis and X-ray Crystallographic Analysis. Preprints 2024, 2024092060. https://doi.org/10.20944/preprints202409.2060.v1
Hijazi, A. K.; Sarayrah, Q. M.; Malkawi, A. W.; Abul-Futouh, H.; Taha, Z. A.; Abusara, O. H.; Daraosheh, A. Q.; Ahmad, A. A. L.; Nureldeen, W. An Insight into the Anticancer and Antibacterial Properties of New 4-(Benzylamino)benzoic Acid Derivatives: Synthesis and X-ray Crystallographic Analysis. Preprints2024, 2024092060. https://doi.org/10.20944/preprints202409.2060.v1
APA Style
Hijazi, A. K., Sarayrah, Q. M., Malkawi, A. W., Abul-Futouh, H., Taha, Z. A., Abusara, O. H., Daraosheh, A. Q., Ahmad, A. A. L., & Nureldeen, W. (2024). An Insight into the Anticancer and Antibacterial Properties of New 4-(Benzylamino)benzoic Acid Derivatives: Synthesis and X-ray Crystallographic Analysis. Preprints. https://doi.org/10.20944/preprints202409.2060.v1
Chicago/Turabian Style
Hijazi, A. K., Ahmad A. L. Ahmad and Waleed Nureldeen. 2024 "An Insight into the Anticancer and Antibacterial Properties of New 4-(Benzylamino)benzoic Acid Derivatives: Synthesis and X-ray Crystallographic Analysis" Preprints. https://doi.org/10.20944/preprints202409.2060.v1
Abstract
A prominent class of reactions, reductive aminations are used extensively in research labs and industry to synthesize amines; which are applied in a variety of medicines, agrochemicals, and biomolecules. Amine compounds are essential in many aspects of life; amino groups exist in many natural and agricultural products. New 4-(benzylamino)benzoic acid derivatives with general formula of C14H12NO2R, where [R= (H), (4-Cl), (4-NMe), (4-Br), (3-NO2), (4-NO2), (2-OMe), (3-OMe), (4-OMe), (2,3-OMe), (3,4-OMe), (2-OH, 3-OMe), (3-OMe, 4-OH), (3,5-OMe, 4-OH), (2-OH, 5-Br), (3-OH), (4-SMe), (2,3-OH), (3-CF3)] (compounds 1-19) were obtained by reductive amination reaction via reacting p-amino benzoic acid with benzaldehyde derivatives and sodium borohydride. All prepared compounds has been characterized by a variety of spectroscopic techniques (HRMS, FT-IR, 1H, and 13C{1H} NMR) and elemental analysis. Furthermore, the structure of some of the synthesized derivatives were confirmed by single crystal X-ray diffraction (R = 4-Cl, 4-Br, 2-OMe, 3-OMe, 4-OMe, 2,3-OMe), compounds 2, 4, 7-9 and 11, respectively. Moreover, some of these new compounds have shown somehow moderate antibacterial activities against different strains of bacteria (gram-positive and gram-negative) with MIC values ranging from 64-256 µg/ mL. The anticancer activities of all compounds (IC50 values, µM) were evaluated against different cell lines, HGF (Fibroblasts; normal cell line), A549 (Non-Small Cell Lung Cancer cell line) and H69 (Small Cell Lung Cancer cell line). Compound 18 showed a considerable IC50 value of 90.69 against A549 and an excellent value of 32.22 and H69, respectively.
Chemistry and Materials Science, Medicinal Chemistry
Copyright:
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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