Design, Synthesis, Biological Evaluation, and in Silico Studies of Novel N-Substituted-2-(3,4,5-Trimethoxyphenyl)-1H-Benzo[D]Imidazole-6-Carboxamides As Promising Anticancer Agents

Design, Synthesis, Biological Evaluation, and in Silico Studies of Novel N-Substituted-2-(3,4,5-Trimethoxyphenyl)-1H-Benzo[D]Imidazole-6-Carboxamides As Promising Anticancer Agents Publisher

Dastyafteh N¹ ; Negahdaripour M^{2, 3} ; Sayahi MH⁴ ; Emami M² ; Ghasemi Y^{2, 3} ; Safaei E⁵ ; Azizian H⁶ ; Pakrouh Jahromi Z^{2, 3} ; Asadi M⁶ ; Mohajeritehrani MR¹ ; Zare F² ; Shahidi M⁷ ; Pooraskari Z⁷ ; Sajjadijazi SM¹ Show All Authors

Dastyafteh N¹
Negahdaripour M^{2, 3}
Sayahi MH⁴
Emami M²
Ghasemi Y^{2, 3}
Safaei E⁵
Azizian H⁶
Pakrouh Jahromi Z^{2, 3}
Asadi M⁶
Mohajeritehrani MR¹
Zare F²
Shahidi M⁷
Pooraskari Z⁷
Sajjadijazi SM¹
Larijani B¹
Mahdavi M¹
Ranjbar S²

Show Affiliations

1. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran
2. Pharmaceutical Sciences Research Center, Shiraz University of Medical Sciences, Shiraz, Iran
3. Department of Pharmaceutical Biotechnology, School of Pharmacy, Shiraz University of Medical Sciences, Iran
4. Department of Chemistry, Payame Noor University, Tehran, Iran
5. School of Chemistry, College of Science, University of Tehran, Tehran, Iran
6. Department of Medicinal Chemistry, School of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
7. Department of Hematology and Blood Transfusion, School of Allied Medicine, Iran University of Medical Sciences, Tehran, Iran

Source: RSC Advances Published:2024

Abstract

Novel benzimidazole-based derivatives were synthesized and their cytotoxic activities were evaluated against two human cancer cells, SW480 and A549, and the normal human MRC-5 cells, using the MTT assay. N-(2,4-Dimethoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-1H-benzo[d]imidazole-6-carboxamide (5o) showed excellent cytotoxicity with IC50 values of 0.15 ± 0.01 and 3.68 ± 0.59 μM against A549 and SW480. Compound 5o had 38.5-, 62.9- and 3.1-fold superior cytotoxicity than cisplatin (IC50 = 5.77 ± 1.60 μM), etoposide (IC50 = 9.44 ± 1.98 μM), and doxorubicin (IC50 = 0.46 ± 0.02 μM), respectively against A549 cells. Moreover, 5o exhibited high selectivity towards A549 (SI = 794.6) and SW480 (SI = 32.4) cancer cells compared with the normal MRC-5. Further studies revealed the ability of 5o to induce apoptosis and arrest the cell cycle at the S phase in A549 cells. Molecular docking studies revealed 5o was well accommodated within the pocket of topoisomerase IIα-DNA, as a possible target. Molecular dynamics simulation studies confirmed the stability of the 5o-IIα-DNA complex. Compound 5o was predicted to have appropriate drug-likeness and pharmacokinetic properties. © 2024 The Royal Society of Chemistry.

Style	Citing Format
MLA	Dastyafteh N, et al.. "Design, Synthesis, Biological Evaluation, and in Silico Studies of Novel N-Substituted-2-(3,4,5-Trimethoxyphenyl)-1H-Benzo[D]Imidazole-6-Carboxamides As Promising Anticancer Agents." RSC Advances, vol. 14, no. 48, 2024, pp. 35323-35335.
APA	Dastyafteh N, Negahdaripour M, Sayahi MH, Emami M, Ghasemi Y, Safaei E, Azizian H, Pakrouh Jahromi Z, Asadi M, Mohajeritehrani MR, Zare F, Shahidi M, Pooraskari Z, Sajjadijazi SM, Larijani B, Mahdavi M, Ranjbar S (2024). Design, Synthesis, Biological Evaluation, and in Silico Studies of Novel N-Substituted-2-(3,4,5-Trimethoxyphenyl)-1H-Benzo[D]Imidazole-6-Carboxamides As Promising Anticancer Agents. RSC Advances, 14(48), 35323-35335.
Chicago	Dastyafteh N, Negahdaripour M, Sayahi MH, Emami M, Ghasemi Y, Safaei E, Azizian H, et al.. "Design, Synthesis, Biological Evaluation, and in Silico Studies of Novel N-Substituted-2-(3,4,5-Trimethoxyphenyl)-1H-Benzo[D]Imidazole-6-Carboxamides As Promising Anticancer Agents." RSC Advances 14, no. 48 (2024): 35323-35335.
Harvard	Dastyafteh N et al. (2024) 'Design, Synthesis, Biological Evaluation, and in Silico Studies of Novel N-Substituted-2-(3,4,5-Trimethoxyphenyl)-1H-Benzo[D]Imidazole-6-Carboxamides As Promising Anticancer Agents', RSC Advances, 14(48), pp. 35323-35335.
Vancouver	Dastyafteh N, Negahdaripour M, Sayahi MH, Emami M, Ghasemi Y, Safaei E, et al.. Design, Synthesis, Biological Evaluation, and in Silico Studies of Novel N-Substituted-2-(3,4,5-Trimethoxyphenyl)-1H-Benzo[D]Imidazole-6-Carboxamides As Promising Anticancer Agents. RSC Advances. 2024;14(48):35323-35335.
BibTex	@article{ author = {Dastyafteh N and Negahdaripour M and Sayahi MH and Emami M and Ghasemi Y and Safaei E and Azizian H and Pakrouh Jahromi Z and Asadi M and Mohajeritehrani MR and Zare F and Shahidi M and Pooraskari Z and Sajjadijazi SM and Larijani B and Mahdavi M and Ranjbar S}, title = {Design, Synthesis, Biological Evaluation, and in Silico Studies of Novel N-Substituted-2-(3,4,5-Trimethoxyphenyl)-1H-Benzo[D]Imidazole-6-Carboxamides As Promising Anticancer Agents}, journal = {RSC Advances}, volume = {14}, number = {48}, pages = {35323-35335}, year = {2024} }
RIS	TY - JOUR AU - Dastyafteh N AU - Negahdaripour M AU - Sayahi MH AU - Emami M AU - Ghasemi Y AU - Safaei E AU - Azizian H AU - Pakrouh Jahromi Z AU - Asadi M AU - Mohajeritehrani MR AU - Zare F AU - Shahidi M AU - Pooraskari Z AU - Sajjadijazi SM AU - Larijani B AU - Mahdavi M AU - Ranjbar S TI - Design, Synthesis, Biological Evaluation, and in Silico Studies of Novel N-Substituted-2-(3,4,5-Trimethoxyphenyl)-1H-Benzo[D]Imidazole-6-Carboxamides As Promising Anticancer Agents JO - RSC Advances VL - 14 IS - 48 SP - 35323 EP - 35335 PY - 2024 ER -

Style

Citing Format

MLA

Dastyafteh N, et al.. "Design, Synthesis, Biological Evaluation, and in Silico Studies of Novel N-Substituted-2-(3,4,5-Trimethoxyphenyl)-1H-Benzo[D]Imidazole-6-Carboxamides As Promising Anticancer Agents." RSC Advances, vol. 14, no. 48, 2024, pp. 35323-35335.

APA

Dastyafteh N, Negahdaripour M, Sayahi MH, Emami M, Ghasemi Y, Safaei E, Azizian H, Pakrouh Jahromi Z, Asadi M, Mohajeritehrani MR, Zare F, Shahidi M, Pooraskari Z, Sajjadijazi SM, Larijani B, Mahdavi M, Ranjbar S (2024). Design, Synthesis, Biological Evaluation, and in Silico Studies of Novel N-Substituted-2-(3,4,5-Trimethoxyphenyl)-1H-Benzo[D]Imidazole-6-Carboxamides As Promising Anticancer Agents. RSC Advances, 14(48), 35323-35335.

Chicago

Dastyafteh N, Negahdaripour M, Sayahi MH, Emami M, Ghasemi Y, Safaei E, Azizian H, et al.. "Design, Synthesis, Biological Evaluation, and in Silico Studies of Novel N-Substituted-2-(3,4,5-Trimethoxyphenyl)-1H-Benzo[D]Imidazole-6-Carboxamides As Promising Anticancer Agents." RSC Advances 14, no. 48 (2024): 35323-35335.

Harvard

Dastyafteh N et al. (2024) 'Design, Synthesis, Biological Evaluation, and in Silico Studies of Novel N-Substituted-2-(3,4,5-Trimethoxyphenyl)-1H-Benzo[D]Imidazole-6-Carboxamides As Promising Anticancer Agents', RSC Advances, 14(48), pp. 35323-35335.

Vancouver

Dastyafteh N, Negahdaripour M, Sayahi MH, Emami M, Ghasemi Y, Safaei E, et al.. Design, Synthesis, Biological Evaluation, and in Silico Studies of Novel N-Substituted-2-(3,4,5-Trimethoxyphenyl)-1H-Benzo[D]Imidazole-6-Carboxamides As Promising Anticancer Agents. RSC Advances. 2024;14(48):35323-35335.

BibTex

@article{ author = {Dastyafteh N and Negahdaripour M and Sayahi MH and Emami M and Ghasemi Y and Safaei E and Azizian H and Pakrouh Jahromi Z and Asadi M and Mohajeritehrani MR and Zare F and Shahidi M and Pooraskari Z and Sajjadijazi SM and Larijani B and Mahdavi M and Ranjbar S}, title = {Design, Synthesis, Biological Evaluation, and in Silico Studies of Novel N-Substituted-2-(3,4,5-Trimethoxyphenyl)-1H-Benzo[D]Imidazole-6-Carboxamides As Promising Anticancer Agents}, journal = {RSC Advances}, volume = {14}, number = {48}, pages = {35323-35335}, year = {2024} }

RIS

TY - JOUR
AU - Dastyafteh N
AU - Negahdaripour M
AU - Sayahi MH
AU - Emami M
AU - Ghasemi Y
AU - Safaei E
AU - Azizian H
AU - Pakrouh Jahromi Z
AU - Asadi M
AU - Mohajeritehrani MR
AU - Zare F
AU - Shahidi M
AU - Pooraskari Z
AU - Sajjadijazi SM
AU - Larijani B
AU - Mahdavi M
AU - Ranjbar S
TI - Design, Synthesis, Biological Evaluation, and in Silico Studies of Novel N-Substituted-2-(3,4,5-Trimethoxyphenyl)-1H-Benzo[D]Imidazole-6-Carboxamides As Promising Anticancer Agents
JO - RSC Advances
VL - 14
IS - 48
SP - 35323
EP - 35335
PY - 2024
ER -

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Authors

Authors Affiliations

Abstract