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Benchmark study of benzamide derivatives and four novel theoretically designed (L1, L2, L3, and L4) ligands and evaluation of their biological properties by DFT approaches

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Abstract

Four novel ligands, namely N-benzhydryl benzamide, N, N-diphenethyl benzamide, N, N-dihexyl benzamide, and N, N-dioctyl benzamide (L1, L2, L3, and L4, respectively), based on the benzamide unit were designed and computed for their different properties, such as absorption spectrum, dipole moment, theoretically expected biological properties, and frontier molecular orbitals, by evaluating the HOMO/LUMO energy orbitals strength with DFT approaches and comparing these properties with the R benzamide properties available in literature. All molecules have a suitable frontier molecular orbital diagram and L1 exhibits maximum absorption at 246.8 nm due to the strong electron donating effect of the diphenylmethane ligand group. Moreover, strongly extended conjugated groups caused a redshift in absorption spectra. Newly designed molecules may show strong biological activities against cancer, bacterial diseases, and harmful fungal disorders.

Orbital energy, electron density and frontier molecular orbitals view of four designed novel benzamide derivates

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Scheme 6.1

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References

  1. Fujita K-i et al (2003) N-alkylation of amines with alcohols catalyzed by a Cp* Ir complex. Tetrahedron Lett 44(13):2687–2690

    Article  CAS  Google Scholar 

  2. Guillena G, Ramón DJ, Yus M (2009) Hydrogen autotransfer in the N-alkylation of amines and related compounds using alcohols and amines as electrophiles. Chem Rev 110(3):1611–1641

    Article  Google Scholar 

  3. Wetzel S et al (2011) Biology-oriented synthesis. Angew Chem Int Ed 50(46):10800–10826

    Article  CAS  Google Scholar 

  4. Zhu Z, Chen D (2002) Nitrogen fertilizer use in China–contributions to food production, impacts on the environment and best management strategies. Nutr Cycl Agroecosyst 63(2–3):117–127

    Article  CAS  Google Scholar 

  5. Weil RR, Brady NC, Weil RR (2016) The nature and properties of soils. Pearson, London

  6. Lv W et al (2017) Synthesis of 2-Alkylaminoquinolines and 1, 8-Naphthyridines by successive ruthenium-catalyzed Dehydrogenative annulation and N-alkylation processes. Adv Synth Catal 359(7):1202–1207

    Article  CAS  Google Scholar 

  7. Bundrick W et al (2003) Levofloxacin versus ciprofloxacin in the treatment of chronic bacterial prostatitis: a randomized double-blind multicenter study. Urology 62(3):537–541

    Article  Google Scholar 

  8. Perkins JC, Devetski M, Dowling M Ampicillin in the treatment

  9. Yunus M, Rahman ASM, Faruque ASG, Glass RI (1981) A clinical trial of ampiciline versus trimethoprimsulfamethoxazole in the treatment of shigella dysentery. Dacca, ICDDRB; 1981

  10. Pearson DC et al (1995) Azathioprine and 6-mercaptopurine in Crohn disease: a meta-analysis. Ann Intern Med 123(2):132–142

    Article  CAS  Google Scholar 

  11. Pearson D et al. (2000) Azathioprine for maintaining remission of Crohn's disease. Cochrane Database Syst Rev (2):CD000067–CD000067

  12. Burghart A et al (1999) 3, 5-Diaryl-4, 4-difluoro-4-bora-3a, 4a-diaza-s-indacene (BODIPY) dyes: synthesis, spectroscopic, electrochemical, and structural properties. J Org Chem 64(21):7813–7819

    Article  CAS  Google Scholar 

  13. Friedli F (2001) Detergency of specialty surfactants 98.

  14. Holmberg K (2003) Novel surfactants: preparation applications and biodegradability, revised and expanded 114. CRC, Boca Raton

  15. Egan R (1978) Cationic surface active agents as fabric softeners. J Am Oil Chem Soc 55(1):118–121

    Article  CAS  Google Scholar 

  16. Yanai T, Tew DP, Handy NC (2004) A new hybrid exchange–correlation functional using the coulomb-attenuating method (CAM-B3LYP). Chem Phys Lett 393(1–3):51–57

    Article  CAS  Google Scholar 

  17. Mohan N et al (2010) Comparison of aromatic NH··· π, OH··· π, and CH··· π interactions of alanine using MP2, CCSD, and DFT methods. J Comput Chem 31(16):2874–2882

    CAS  PubMed  Google Scholar 

  18. Chattaraj PK, Bhaumik S, Niser B Check of size consistency in different levels of theory

  19. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb M, Cheeseman JR et al (2009) Gaussian 09, revision D. 01. Gaussian, Inc., Wallingford, CT

  20. Dennington RD, Keith TA, Millam JM (2008) GaussView 5.0. 8. Gaussian Inc, Wallingford

  21. Civalleri B et al (2008) B3LYP augmented with an empirical dispersion term (B3LYP-D*) as applied to molecular crystals. Cryst Eng Comm 10(4):405–410

    Article  CAS  Google Scholar 

  22. Adamo C, Barone V (1998) Exchange functionals with improved long-range behavior and adiabatic connection methods without adjustable parameters: the m PW and m PW1PW models. J Chem Phys 108(2):664–675

    Article  CAS  Google Scholar 

  23. Chai J-D, Head-Gordon M (2008) Long-range corrected hybrid density functionals with damped atom–atom dispersion corrections. Phys Chem Chem Phys 10(44):6615–6620

    Article  CAS  Google Scholar 

  24. Yu C, Hao X, Shen Q (2010) Illustration of origin 8.0. Chemical Industry Press, Beijing

  25. Tenderholt AL (2006) PyMOlyze: a program to analyze quantum chemistry calculations, version 2.0.

  26. Mariappan A, Das KM, Jeganmohan M (2018) Remote alkylation of N-(quinolin-8-yl) benzamides with alkyl bromides via ruthenium (ii)-catalyzed C–H bond activation. Org Biomolec Chem 16(18):3419–3427

    Article  CAS  Google Scholar 

  27. Srivastava SK, Chauhan PMS, Bhaduri AP (1999) A novel strategy for N-alkylation of primary amines. Synth Commun 29(12):2085–2091

    Article  CAS  Google Scholar 

  28. Daniel P et al. (2018) Palladium-catalyzed synthesis of α-trifluoromethyl benzylic amines via fluoroarylation of gem-difluoro-2-azadienes enabled by phosphine-catalyzed formation of an azaallyl–silver intermediate. ACS Catal 9(1):205–210

  29. Wolf M et al (2005) Alkylating benzamides with melanoma cytotoxicity: role of melanin, tyrosinase, intracellular pH and DNA interaction. Melanoma Res 15(5):383–391

    Article  CAS  Google Scholar 

  30. Han C et al (2004) Copper-mediated synthesis of N-acyl vinylogous carbamic acids and derivatives: synthesis of the antibiotic CJ-15,801. Org Lett 6(1):27–30

    Article  CAS  Google Scholar 

  31. Shalaby AA et al (2000) Synthesis and antifungal activity of some new quinazoline and benzoxazinone derivatives. Archiv der Pharmazie: Int J Pharmaceut Med Chem 333(11):365–372

    Article  CAS  Google Scholar 

  32. Muktapuram PR et al (2012) Anticancer siRNA delivery by new anticancer molecule: a novel combination strategy for cancer cell killing. Eur J Med Chem 56:400–408

    Article  CAS  Google Scholar 

  33. Abdizadeh T et al (2017) Design, synthesis and biological evaluation of novel coumarin-based benzamides as potent histone deacetylase inhibitors and anticancer agents. Eur J Med Chem 132:42–62

    Article  CAS  Google Scholar 

  34. Prajapati AK, Modi VP (2011) Synthesis and biological activity of n-{5-(4-methylphenyl) diazenyl-4-phenyl-1, 3-thiazol-2-yl} benzamide derivatives. Química Nova 34(5):771–774

    CAS  Google Scholar 

Download references

Acknowledgments

The Computations/simulations/SIMILAR were performed on resources provided by the Swedish National Infrastructure for Computing (SNIC) at Umeå University, 901 87, Umeå, Sweden. The authors acknowledge the financial and technical support from Punjab Bio-energy Institute (PBI), University of Agriculture Faisalabad (UAF). Dr. MAI is thankful to HEC-Pakistan for awarding research Project NRPU-8396.

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Authors and Affiliations

  1. Department of Chemistry, University of Agriculture Faisalabad, Faisalabad, 38040, Pakistan

    Amanullah, Usman Ali, Muhammad Ans, Javed Iqbal, Muhammad Adnan Iqbal & Muhammad Shoaib

  2. Punjab Bio-energy Institute, University of Agriculture, Faisalabad, 38040, Pakistan

    Javed Iqbal

  3. Organometallic and Coordination Chemistry Laboratory, Department of Chemistry, University of Agriculture, Faisalabad, 38040, Pakistan

    Muhammad Adnan Iqbal

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  1. Amanullah
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  2. Usman Ali
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  3. Muhammad Ans
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  4. Javed Iqbal
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  5. Muhammad Adnan Iqbal
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  6. Muhammad Shoaib
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Correspondence to Usman Ali, Javed Iqbal or Muhammad Adnan Iqbal.

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Amanullah, Ali, U., Ans, M. et al. Benchmark study of benzamide derivatives and four novel theoretically designed (L1, L2, L3, and L4) ligands and evaluation of their biological properties by DFT approaches. J Mol Model 25, 223 (2019). https://doi.org/10.1007/s00894-019-4115-3

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  • DOI: https://doi.org/10.1007/s00894-019-4115-3

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