The aim of this study is to prepare a novel precursor for the synthesis of imidazo[5,4- f]benzimidazole(imino)quinone. This will target the over-expression of the enzyme NAD(P)H: quinone oxidoreductase (NQO1) in solid tumours. An electron withdrawing group was incorporated into the structure, and the substituted ring size was reduced as this is hypothesised to increase its binding affinity to NQO1. The 2, 5-difluoroaniline was acetylated using acetic anhydride to produce N-(2,5-difluorophenyl) acetamide. The latter underwent selective nitration to produce N-(2,5-difluoro- 4-nitrophenyl) acetamide followed by oxidation using methane sulfonic acid and hydrogen peroxide to give 1,4-difluoro-2,5-dinitrobenzene. The synthesized precursor was achieved by the double nucleophilic aromatic substitution of morpholine and pyrrolidine onto 1,4-difluoro-2,5-dinitrobenzene. The 4-(2,5-dinitro-4-pyrrolid-1-yl) morpholine was successfully synthesized in four synthetic steps. The identity and purity were confirmed using NMR with peaks assigned using proton-fluorine coupling values. Further work is recommended for the developments of this study, additional synthetic steps using the novel precursor need to be carried out to achieve oxazino[4,3-a] pyrroloimidazo[5,4-f] benzimidazole(imino)quinone.
| Published in | International Journal of Pharmacy and Chemistry (Volume 7, Issue 5) |
| DOI | 10.11648/j.ijpc.20210705.12 |
| Page(s) | 85-100 |
| Creative Commons |
This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited. |
| Copyright |
Copyright © The Author(s), 2021. Published by Science Publishing Group |
NAD(P)H: Quinone Oxidoreductase, National Cancer Institute, COMPARE Analysis, Computational Docking, 4-(2,5-dinitro-4-pyrrolid-1-yl) Morpholine, Imidazo[5,4-f]benzimidazole (imino)quinone
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APA Style
Mohammed Yaqob Shareef, Noor Mohammed Yaqob Shareef. (2021). Recent Progress in Preparation and Applications of Oxazino[4,3-a] pyrroloimidazo[5,4-f]benzimidazole (imino)quinone as an Anti-Cancer Agent. International Journal of Pharmacy and Chemistry, 7(5), 85-100. https://doi.org/10.11648/j.ijpc.20210705.12
ACS Style
Mohammed Yaqob Shareef; Noor Mohammed Yaqob Shareef. Recent Progress in Preparation and Applications of Oxazino[4,3-a] pyrroloimidazo[5,4-f]benzimidazole (imino)quinone as an Anti-Cancer Agent. Int. J. Pharm. Chem. 2021, 7(5), 85-100. doi: 10.11648/j.ijpc.20210705.12
AMA Style
Mohammed Yaqob Shareef, Noor Mohammed Yaqob Shareef. Recent Progress in Preparation and Applications of Oxazino[4,3-a] pyrroloimidazo[5,4-f]benzimidazole (imino)quinone as an Anti-Cancer Agent. Int J Pharm Chem. 2021;7(5):85-100. doi: 10.11648/j.ijpc.20210705.12
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Download@article{10.11648/j.ijpc.20210705.12,
author = {Mohammed Yaqob Shareef and Noor Mohammed Yaqob Shareef},
title = {Recent Progress in Preparation and Applications of Oxazino[4,3-a] pyrroloimidazo[5,4-f]benzimidazole (imino)quinone as an Anti-Cancer Agent},
journal = {International Journal of Pharmacy and Chemistry},
volume = {7},
number = {5},
pages = {85-100},
doi = {10.11648/j.ijpc.20210705.12},
url = {https://doi.org/10.11648/j.ijpc.20210705.12},
eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ijpc.20210705.12},
abstract = {The aim of this study is to prepare a novel precursor for the synthesis of imidazo[5,4- f]benzimidazole(imino)quinone. This will target the over-expression of the enzyme NAD(P)H: quinone oxidoreductase (NQO1) in solid tumours. An electron withdrawing group was incorporated into the structure, and the substituted ring size was reduced as this is hypothesised to increase its binding affinity to NQO1. The 2, 5-difluoroaniline was acetylated using acetic anhydride to produce N-(2,5-difluorophenyl) acetamide. The latter underwent selective nitration to produce N-(2,5-difluoro- 4-nitrophenyl) acetamide followed by oxidation using methane sulfonic acid and hydrogen peroxide to give 1,4-difluoro-2,5-dinitrobenzene. The synthesized precursor was achieved by the double nucleophilic aromatic substitution of morpholine and pyrrolidine onto 1,4-difluoro-2,5-dinitrobenzene. The 4-(2,5-dinitro-4-pyrrolid-1-yl) morpholine was successfully synthesized in four synthetic steps. The identity and purity were confirmed using NMR with peaks assigned using proton-fluorine coupling values. Further work is recommended for the developments of this study, additional synthetic steps using the novel precursor need to be carried out to achieve oxazino[4,3-a] pyrroloimidazo[5,4-f] benzimidazole(imino)quinone.},
year = {2021}
}
TY - JOUR T1 - Recent Progress in Preparation and Applications of Oxazino[4,3-a] pyrroloimidazo[5,4-f]benzimidazole (imino)quinone as an Anti-Cancer Agent AU - Mohammed Yaqob Shareef AU - Noor Mohammed Yaqob Shareef Y1 - 2021/09/15 PY - 2021 N1 - https://doi.org/10.11648/j.ijpc.20210705.12 DO - 10.11648/j.ijpc.20210705.12 T2 - International Journal of Pharmacy and Chemistry JF - International Journal of Pharmacy and Chemistry JO - International Journal of Pharmacy and Chemistry SP - 85 EP - 100 PB - Science Publishing Group SN - 2575-5749 UR - https://doi.org/10.11648/j.ijpc.20210705.12 AB - The aim of this study is to prepare a novel precursor for the synthesis of imidazo[5,4- f]benzimidazole(imino)quinone. This will target the over-expression of the enzyme NAD(P)H: quinone oxidoreductase (NQO1) in solid tumours. An electron withdrawing group was incorporated into the structure, and the substituted ring size was reduced as this is hypothesised to increase its binding affinity to NQO1. The 2, 5-difluoroaniline was acetylated using acetic anhydride to produce N-(2,5-difluorophenyl) acetamide. The latter underwent selective nitration to produce N-(2,5-difluoro- 4-nitrophenyl) acetamide followed by oxidation using methane sulfonic acid and hydrogen peroxide to give 1,4-difluoro-2,5-dinitrobenzene. The synthesized precursor was achieved by the double nucleophilic aromatic substitution of morpholine and pyrrolidine onto 1,4-difluoro-2,5-dinitrobenzene. The 4-(2,5-dinitro-4-pyrrolid-1-yl) morpholine was successfully synthesized in four synthetic steps. The identity and purity were confirmed using NMR with peaks assigned using proton-fluorine coupling values. Further work is recommended for the developments of this study, additional synthetic steps using the novel precursor need to be carried out to achieve oxazino[4,3-a] pyrroloimidazo[5,4-f] benzimidazole(imino)quinone. VL - 7 IS - 5 ER -
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