Processing, Please wait...

  • Home
  • About Us
  • Search:
  • Advanced Search

Growing Science » Current Chemistry Letters » Mechanistic insights and antifungal assessment of (3+2) cycloaddition products of 2-diazopropane and 5-hydroxy-3-methyl-1,5-dihydropyrrol-2-one derivatives

Journals

  • IJIEC (777)
  • MSL (2643)
  • DSL (690)
  • CCL (528)
  • USCM (1092)
  • ESM (421)
  • AC (562)
  • JPM (293)
  • IJDS (952)
  • JFS (101)
  • HE (32)
  • SCI (26)

CCL Volumes

    • Volume 1 (23)
      • Issue 1 (7)
      • Issue 2 (5)
      • Issue 3 (6)
      • Issue 4 (5)
    • Volume 2 (26)
      • Issue 1 (7)
      • Issue 2 (6)
      • Issue 3 (6)
      • Issue 4 (7)
    • Volume 3 (30)
      • Issue 1 (7)
      • Issue 2 (10)
      • Issue 3 (8)
      • Issue 4 (5)
    • Volume 4 (21)
      • Issue 1 (5)
      • Issue 2 (5)
      • Issue 3 (6)
      • Issue 4 (5)
    • Volume 5 (20)
      • Issue 1 (5)
      • Issue 2 (5)
      • Issue 3 (5)
      • Issue 4 (5)
    • Volume 6 (20)
      • Issue 1 (5)
      • Issue 2 (5)
      • Issue 3 (5)
      • Issue 4 (5)
    • Volume 7 (15)
      • Issue 1 (4)
      • Issue 2 (4)
      • Issue 3 (4)
      • Issue 4 (3)
    • Volume 8 (20)
      • Issue 1 (5)
      • Issue 2 (5)
      • Issue 3 (5)
      • Issue 4 (5)
    • Volume 9 (20)
      • Issue 1 (5)
      • Issue 2 (5)
      • Issue 3 (5)
      • Issue 4 (5)
    • Volume 10 (43)
      • Issue 1 (5)
      • Issue 2 (7)
      • Issue 3 (17)
      • Issue 4 (14)
    • Volume 11 (43)
      • Issue 1 (14)
      • Issue 2 (11)
      • Issue 3 (10)
      • Issue 4 (8)
    • Volume 12 (78)
      • Issue 1 (21)
      • Issue 2 (22)
      • Issue 3 (20)
      • Issue 4 (15)
    • Volume 13 (68)
      • Issue 1 (23)
      • Issue 2 (17)
      • Issue 3 (16)
      • Issue 4 (12)
    • Volume 14 (68)
      • Issue 1 (20)
      • Issue 2 (13)
      • Issue 3 (22)
      • Issue 4 (13)
    • Volume 15 (33)
      • Issue 1 (13)
      • Issue 2 (20)

Keywords

Supply chain management(168)
Jordan(165)
Vietnam(151)
Customer satisfaction(120)
Performance(115)
Supply chain(112)
Service quality(98)
Competitive advantage(97)
Tehran Stock Exchange(94)
SMEs(89)
optimization(87)
Sustainability(86)
Artificial intelligence(85)
Financial performance(84)
Trust(83)
TOPSIS(83)
Job satisfaction(81)
Genetic Algorithm(78)
Factor analysis(78)
Social media(78)


» Show all keywords

Authors

Naser Azad(82)
Zeplin Jiwa Husada Tarigan(66)
Mohammad Reza Iravani(64)
Endri Endri(45)
Muhammad Alshurideh(42)
Hotlan Siagian(40)
Dmaithan Almajali(37)
Jumadil Saputra(36)
Muhammad Turki Alshurideh(35)
Ahmad Makui(33)
Barween Al Kurdi(32)
Hassan Ghodrati(31)
Basrowi Basrowi(31)
Sautma Ronni Basana(31)
Mohammad Khodaei Valahzaghard(30)
Shankar Chakraborty(29)
Ni Nyoman Kerti Yasa(29)
Haitham M. Alzoubi(28)
Sulieman Ibraheem Shelash Al-Hawary(28)
Prasadja Ricardianto(28)


» Show all authors

Countries

Iran(2192)
Indonesia(1311)
Jordan(813)
India(793)
Vietnam(510)
Saudi Arabia(478)
Malaysia(444)
China(231)
United Arab Emirates(226)
Thailand(160)
United States(114)
Ukraine(110)
Turkey(110)
Egypt(106)
Peru(94)
Canada(93)
Morocco(86)
Pakistan(85)
United Kingdom(80)
Nigeria(78)


» Show all countries

Current Chemistry Letters

ISSN 1927-730x (Online) - ISSN 1927-7296 (Print)
Quarterly Publication
Volume 14 Issue 3 pp. 547-558 , 2025

Mechanistic insights and antifungal assessment of (3+2) cycloaddition products of 2-diazopropane and 5-hydroxy-3-methyl-1,5-dihydropyrrol-2-one derivatives Pages 547-558 Right click to download the paper Download PDF

Authors: Abdeljabbar Jaddi, Amine Rafik, Saloua Sebbahi, Mohammed Salah, Khadija Marakchi

DOI: 10.5267/j.ccl.2025.3.003

Keywords:

Abstract: The (3+2) cycloaddition reactions of 2-diazopropane with derivatives of 5-hydroxy-3-methyl-1,5-dihydropyrrol-2-one were investigated using Molecular Electron Density Theory. Calculations were performed at the wB97XD/6-311++G(d,p) level of theory. Conceptual Density Functional Theory indices revealed a low polar character for these reactions, supported by a minimal global electron density transfer at the transition structures, which were classified as forward electron density flux processes. The Electron Localization Function analysis identified 2-diazopropane as a pseudo(mono)radical three-atom component. It further indicated that bond formation does not start at the transition structures. Mechanistically, these reactions proceed via an asynchronous one-step mechanism, ultimately leading to products that are kinetically favored. Furthermore, molecular docking studies were conducted to evaluate the antifungal potential of the reaction products against pathogenic fungal strains, Candida albicans and Aspergillus fumigatus. The docking analysis assessed binding affinities and characterized molecular interactions between the proposed compounds and critical fungal proteins, highlighting their potential as antifungal agents.

How to cite this paper
Jaddi, A., Rafik, A., Sebbahi, S., Salah, M & Marakchi, K. (2025). Mechanistic insights and antifungal assessment of (3+2) cycloaddition products of 2-diazopropane and 5-hydroxy-3-methyl-1,5-dihydropyrrol-2-one derivatives.Current Chemistry Letters, 14(3), 547-558.

Refrences
1. Padwa A., and Pearson W. H. (2002) Synthetic Applications of 1,3‐Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products, 1st ed. Wiley. 2. Domingo L. (2016) Molecular Electron Density Theory: A Modern View of Reactivity in Organic Chemistry. Molecules, 21, 1319. https://doi.org/10.3390/molecules21101319 3. Ríos‐Gutiérrez M., and Domingo L. R. (2019) Unravelling the Mysteries of the [3+2] Cycloaddition Reactions. Eur J Org Chem., 2019, 267–282. https://doi.org/10.1002/ejoc.201800916 4. Al-Hazmy S., Zouaghi M., Amri N., Arfaoui Y., Alhagri I., and Hamdi N. (2023) DFT Study of Regio- and Stereoselective 13DC Reaction between Diazopropane and Substituted Chalcone Derivatives: Molecular Docking of Novel Pyrazole Derivatives as Anti-Alzheimer’s Agents. Molecules, 28, 1899. https://doi.org/10.3390/molecules28041899 5. Shybanov D. E., Kukushkin M. E., Grishin Y. K., Roznyatovsky V. A., Tafeenko V. A., Abo Qoura L., Pokrovsky V. S., Yarovaya O. I., Belyaevskaya S. V., Volobueva, A. S., Volobueva A. S., Esaulkova I. L., Zarubaev V. V., and Beloglazkina E. K. (2024) 1,3-Dipolar Cycloaddition of Nitrile Oxides and Nitrilimines to (−)-β-Caryophyllene: Stereoselective Synthesis of Polycyclic Derivatives and Their Biological Testing. Int J Mol Sci., 25, 11435. https://doi.org/10.3390/ijms252111435 6. Boukamcha N., Gharbi R., Martin M. -T., Chiaroni A., Mighri Z., and Khemiss A. (1999) Steroe- and chemoselectivity in 1,3-dipolar cycloaddition reaction of 2-diazopropane with diarylidenacetones. Tetrahedron, 55, 449–460. https://doi.org/10.1016/S0040-4020(98)01056-4 7. Almahdi M. M., Saeed A. E. M., and Metwally N. H. (2019) Synthesis and antimicrobial activity of some new pyrazoline derivatives bearing sulfanilamido moiety. Eur J Chem., 10, 30–36. https://doi.org/10.5155/eurjchem.10.1.30-36.1791 8. Andrew T. L., Cox J. R., and Swager T. M. (2010) Synthesis, Reactivity, and Electronic Properties of 6,6-Dicyanofulvenes. Org Lett., 12, 5302–5305. https://doi.org/10.1021/ol102384k 9. Hassan S. (2013) Synthesis, Antibacterial and Antifungal Activity of Some New Pyrazoline and Pyrazole Derivatives. Molecules, 18, 2683–2711. https://doi.org/10.3390/molecules18032683 10. Ravindar L., Hasbullah S. A., Rakesh K. P., and Hassan N. I. (2023) Pyrazole and pyrazoline derivatives as antimalarial agents: A key review. Eur J Pharm Sci., 183, 106365. https://doi.org/10.1016/j.ejps.2022.106365 11. Haider K., Shafeeque M., Yahya S., and Yar M. S. (2022) A comprehensive review on pyrazoline based heterocyclic hybrids as potent anticancer agents. Eur J Med Chem Rep., 5, 100042. https://doi.org/10.1016/j.ejmcr.2022.100042 12. Domingo L. R., Ríos-Gutiérrez M., and Pérez P. (2018) A Molecular Electron Density Theory Study of the Reactivity and Selectivities in [3 + 2] Cycloaddition Reactions of C , N -Dialkyl Nitrones with Ethylene Derivatives. J Org Chem., 83, 2182–2197. https://doi.org/10.1021/acs.joc.7b03093 13. Acharjee N. (2020) Unravelling the regio- and stereoselective synthesis of bicyclic N,O-nucleoside analogues within the molecular electron density theory perspective. Struct Chem., 31, 2147–2160. https://doi.org/10.1007/s11224-020-01569-x 14. Domingo L. R., Ríos-Gutiérrez M., and Acharjee N. (2019) A Molecular Electron Density Theory Study of the Chemoselectivity, Regioselectivity, and Diastereofacial Selectivity in the Synthesis of an Anticancer Spiroisoxazoline derived from α-Santonin. Molecules, 24, 832. https://doi.org/10.3390/molecules24050832 15. Domingo L., Acharjee N., and Mohammad-Salim H. (2020) Understanding the Reactivity of Trimethylsilyldiazoalkanes Participating in [3+2] Cycloaddition Reactions towards Diethylfumarate with a Molecular Electron Density Theory Perspective. Organics, 1, 3–18. https://doi.org/10.3390/org1010002 16. Domingo L. R, and Acharjee N. (2018) [3+2] Cycloaddition Reaction of C ‐Phenyl‐ N ‐methyl Nitrone to Acyclic‐Olefin‐Bearing Electron‐Donating Substituent: A Molecular Electron Density Theory Study. ChemistrySelect., 3, 8373–8380. https://doi.org/10.1002/slct.201801528 17. Mondal A., Mohammad-Salim H. A., and Acharjee N. (2023) Unveiling substituent effects in [3+2] cycloaddition reactions of benzonitrile N-oxide and benzylideneanilines from the molecular electron density theory perspective. Sci Radices, 2, 75–92. https://doi.org/10.58332/scirad2023v2i1a05 18. Ben Hamadi N., and Msaddek M. (2011) 1,3-dipolar cycloadditions of arylnitrile oxides and 2-diazopropane with 5-hydroxy-3-methyl-1,5-dihydropyrrol-2-one derivatives. Comptes Rendus Chim., 14, 891–895. https://doi.org/10.1016/j.crci.2011.02.005 19. Becke A. D., and Edgecombe K. E. (1990) A simple measure of electron localization in atomic and molecular systems. J Chem Phys., 92, 5397–5403. https://doi.org/10.1063/1.458517 20. Silvi B., and Savin A. (1994) Classification of chemical bonds based on topological analysis of electron localization functions. Nature, 371, 683–686. https://doi.org/10.1038/371683a0 21. Geerlings P., De Proft F., and Langenaeker W. (2003) Conceptual Density Functional Theory. Chem Rev., 103, 1793–1874. https://doi.org/10.1021/cr990029p 22. Domingo L., Ríos-Gutiérrez M., and Pérez P. (2016) Applications of the Conceptual Density Functional Theory Indices to Organic Chemistry Reactivity. Molecules, 21, 748. https://doi.org/10.3390/molecules21060748 23. Bader R. F. W., and Essén H. (1984) The characterization of atomic interactions. J Chem Phys., 80, 1943–1960. https://doi.org/10.1063/1.446956 24. Fisher M. C., Alastruey-Izquierdo A., Berman J., Bicanic T., Bignell E. M., Bowyer P., Bromley M., Brüggemann R., Garber G., Cornely O. A., Gurr S. J., Harrison T. S., Kuijper E., Rhodes J., Sheppard D. C., Warris A., White P. L, Xu J., Zwaan B., and Verweij P. E. (2022) Tackling the emerging threat of antifungal resistance to human health. Nat Rev Microbiol., 20, 557–571. https://doi.org/10.1038/s41579-022-00720-1 25. Lopes J. P, and Lionakis M. S. (2022) Pathogenesis and virulence of Candida albicans. Virulence, 13, 89–121. https://doi.org/10.1080/21505594.2021.2019950 26. Shinu P., Gupta G. L., Sharma M., Khan S., Goyal M., Nair A. B., Kumar M., Soliman W.E., Rahman A., Attimarad M., Venugopala K. N, and Altaweel A. A. A. (2023) Pharmacological Features of 18β-Glycyrrhetinic Acid: A Pentacyclic Triterpenoid of Therapeutic Potential. Plants, 12, 1086. https://doi.org/10.3390/plants12051086 27. Arastehfar A., Carvalho A., Houbraken J., Lombardi L., Garcia-Rubio R., Jenks J. D., Rivero-Menendez O., Aljohani R., Jacobsen I. D., Berman J., Osherov N., Hedayati M. T., Ilkit M., Armstrong-James D., Gabaldón T., Meletiadis J., Kostrzewa M., Pan W., Lass-Flörl .C, Perlin D. S., and Hoenigl M. (2021) Aspergillus fumigatus and aspergillosis: From basics to clinics. Stud Mycol., 100, 100115–100115. https://doi.org/10.1016/j.simyco.2021.100115 28. Calais J. (1993) Density‐functional theory of atoms and molecules. R.G. Parr and W. Yang, Oxford University Press, New York, Oxford, 1989. IX + 333 pp. Price £45.00. Int J Quantum Chem., 47, 101–101. https://doi.org/10.1002/qua.560470107 29. Chai J-D., and Head-Gordon M. (2008) Long-range corrected hybrid density functionals with damped atom–atom dispersion corrections. Phys Chem Chem Phys., 10, 6615. https://doi.org/10.1039/b810189b 30. Schlegel H. B. (1982) Optimization of equilibrium geometries and transition structures. J Comput Chem., 3, 214–218. https://doi.org/10.1002/jcc.540030212 31. Gonzalez C., and Schlegel H. B. (1989) An improved algorithm for reaction path following. J Chem Phys., 90, 2154–2161. https://doi.org/10.1063/1.456010 32. Pearson R. G. (1992) The electronic chemical potential and chemical hardness. J Mol Struct THEOCHEM, 255, 261–270. https://doi.org/10.1016/0166-1280(92)85014-C 33. Domingo L. R., and Pérez P. (2011) The nucleophilicity N index in organic chemistry. Org Biomol Chem., 9, 7168. https://doi.org/10.1039/c1ob05856h 34. Domingo L. R., Pérez P., and Sáez J. A. (2013) Understanding the local reactivity in polar organic reactions through electrophilic and nucleophilic Parr functions. RSC Adv., 3, 1486–1494. https://doi.org/10.1039/C2RA22886F 35. Domingo L. R. (2014) A new C–C bond formation model based on the quantum chemical topology of electron density. RSC Adv., 4, 32415–32428. https://doi.org/10.1039/C4RA04280H 36. Frisch M. J., Trucks G. W., Schlegel H. B., Scuseria G. E., Robb M. A., Cheeseman J. R., Scalmani G., Barone V., Mennucci B., Petersson G. A., Nakatsuji H., Caricato M., Li X., Hratchian H. P., Izmaylov A. F., Bloino J., Zheng G., Sonnenberg J. L., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Vreven T., Montgomery J. A. Jr., Peralta J. E., Ogliaro F., Bearpark M., Heyd J. J., Brothers E., Kudin K. N., Staroverov V. N., Kobayashi R., Normand J., Raghavachari K., Rendell A., Burant J. C., Iyengar S. S., Tomasi J., Cossi M., Rega N., Millam J. M., Klene M., Knox J. E., Cross J. B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R. E., Yazyev O., Austin A. J., Cammi R., Pomelli C., Ochterski J. W., Martin R. L., Morokuma K., Zakrzewski V. G., Voth G. A., Salvador P., Dannenberg J. J., Dapprich S., Daniels A. D., Farkas O., Foresman J. B., Ortiz J. V., Cioslowski J., and Fox D. J. (2009) Gaussian 09, Revision A.02, Gaussian, Inc., Wallingford CT. 37. Lu T., and Chen F. (2012) Multiwfn: A multifunctional wavefunction analyzer. J Comput Chem., 33, 580–592. https://doi.org/10.1002/jcc.22885 38. Lu T., and Chen Q. (2022) Independent gradient model based on Hirshfeld partition: A new method for visual study of interactions in chemical systems. J Comput Chem., 43, 539–555. https://doi.org/10.1002/jcc.26812 39. Rafik A., Jaddi A., Salah M., Komiha N., Carvajal M., and Marakchi K. (2024) Insights into the mechanism, selectivity, and substituent effects in the Diels-Alder reaction of azatrienes with electron-rich dienophiles: An MEDT study. J Mol Graph Model., 132, 108819. https://doi.org/10.1016/j.jmgm.2024.108819 40. Noury S., Krokidis X., Fuster F., and Silvi B. (1999) Computational tools for the electron localization function topological analysis. Comput Chem., 23, 597–604. https://doi.org/10.1016/S0097-8485(99)00039-X 41. Dennington R., Keith T. A., and Millam J. M. (2016) GaussView, Version 6.1. Semichem Inc., Shawnee Mission, KS. 42. Humphrey W., Dalke A., and Schulten K. (1996) VMD: Visual molecular dynamics. J Mol Graph., 14, 33–38. https://doi.org/10.1016/0263-7855(96)00018-5 43. Agu P. C., Afiukwa C. A., Orji O. U., Ezeh E. M., Ofoke I. H., Ogbu C. O., Ugwuja E. I., and Aja P. M. (2023) Molecular docking as a tool for the discovery of molecular targets of nutraceuticals in diseases management. Sci Rep., 13, 13398. https://doi.org/10.1038/s41598-023-40160-2 44. Trott O., and Olson A. J. (2010) AutoDock Vina: Improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. J Comput Chem., 31, 455–461. https://doi.org/10.1002/jcc.21334 45. Vilar S., Cozza G., and Moro S. (2008) Medicinal Chemistry and the Molecular Operating Environment (MOE): Application of QSAR and Molecular Docking to Drug Discovery. Curr Top Med Chem., 8, 1555–1572. https://doi.org/10.2174/156802608786786624 46. Krokidis X., Noury S., and Silvi B. (1997) Characterization of Elementary Chemical Processes by Catastrophe Theory. J Phys Chem A., 101, 7277–7282. https://doi.org/10.1021/jp9711508 47. Ríos‐Gutiérrez M., Saz Sousa A., and Domingo L. R. (2023) Electrophilicity and nucleophilicity scales at different DFT computational levels. J Phys Org Chem., 36, e4503. https://doi.org/10.1002/poc.4503 48. Domingo L. R., and Sáez J. A. (2011) Understanding the Electronic Reorganization along the Nonpolar [3 + 2] Cycloaddition Reactions of Carbonyl Ylides. J Org Chem., 76, 373–379. https://doi.org/10.1021/jo101367v 49. Domingo L. R. (1999) Theoretical Study of the 1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides. A DFT Study of Reaction between Trifluoromethyl Thiomethyl Azomethine Ylide and Acronitrile. J Org Chem., 64, 3922–3929. https://doi.org/10.1021/jo9822683 50. Marakchi K., Ghailane R., Kabbaj O. K., and Komiha N. (2014) DFT study of the mechanism and stereoselectivity of the 1,3-dipolar cycloaddition between pyrroline-1-oxide and methyl crotonate. J Chem Sci., 126, 283–292. https://doi.org/10.1007/s12039-013-0563-y
  • 0
  • 1
  • 2
  • 3
  • 4
  • 5

Journal: Current Chemistry Letters | Year: 2025 | Volume: 14 | Issue: 3 | Views: 265 | Reviews: 0

Related Articles:
  • An MEDT study of Diels-Alder reactions of a tetrahydroazulenone with maleim ...
  • Molecular docking against Covid-19 and HIV, and the role of catalysis in st ...
  • Advanced quantum and docking studies on the [3+2] cycloaddition of nitrile ...
  • Molecular docking, elucidating the regiospecificity and the mechanism of [3 ...
  • Exploration of regiospecificity phenomenon in [2+3] cycloaddition reactions ...

Add Reviews

Name:*
E-Mail:
Review:
Bold Italic Underline Strike | Align left Center Align right | Insert smilies Insert link URLInsert protected URL Select color | Add Hidden Text Insert Quote Convert selected text from selection to Cyrillic (Russian) alphabet Insert spoiler
winkwinkedsmileam
belayfeelfellowlaughing
lollovenorecourse
requestsadtonguewassat
cryingwhatbullyangry
Security Code: *
Include security image CAPCHA.
Refresh Code

® 2010-2026 GrowingScience.Com