{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,23]],"date-time":"2026-08-23T15:20:21Z","timestamp":1787498421076,"version":"build-2736575974"},"reference-count":66,"publisher":"MDPI AG","issue":"13","license":[{"start":{"date-parts":[[2023,6,27]],"date-time":"2023-06-27T00:00:00Z","timestamp":1687824000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"HEC, Pakistan"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The pharmacological effectiveness of indoles, benzoxazepines and benzodiazepines initiated our synthesis of indole fused benoxazepine\/benzodiazepine heterocycles, along with enhanced biological usefulness of the fused rings. Activated indoles 5, 6 and 7 were synthesized using modified Bischler indole synthesis rearrangement. Indole 5 was substituted with the trichloroacetyl group at the C7 position, yielding 8, exclusively due to the increased nucleophilic character of C7. When trichloroacylated indole 8 was treated with basified ethanol or excess amminia, indole acid 9 and amide 10 were yielded, respectively. Indole amide 10 was expected to give indole fused benoxazepine\/benzodiazepine 11a\/11b on treatment with alpha halo ester followed by a coupling agent, but when the reaction was tried, an unexpectedly rearranged novel product, 1,3-bezodiazine 12, was obtained. The synthetic compounds were screened for anticholinesterase and antibacterial potential; results showed all products to be very important candidates for both activities, and their potential can be explored further. In addition, 1,3-bezodiazine 12 was explored by DFT studies, Hirshfeld surface charge analysis and structural insight to obrain a good picture of the structure and reactivity of the products for the design of derivatised drugs from the novel compound.<\/jats:p>","DOI":"10.3390\/molecules28135024","type":"journal-article","created":{"date-parts":[[2023,6,28]],"date-time":"2023-06-28T00:45:11Z","timestamp":1687913111000},"page":"5024","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":24,"title":["Evaluation of Antimicrobial, Anticholinesterase Potential of Indole Derivatives and Unexpectedly Synthesized Novel Benzodiazine: Characterization, DFT and Hirshfeld Charge Analysis"],"prefix":"10.3390","volume":"28","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-4053-4862","authenticated-orcid":false,"given":"Abdul Rauf","family":"Raza","sequence":"first","affiliation":[{"name":"Institute of Chemistry, Ibn e Sina Block, University of Sargodha, Sargodha 40100, Pakistan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Syeda Laila","family":"Rubab","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Division of Science and Technology, University of Education, Lahore 54770, Pakistan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6663-8777","authenticated-orcid":false,"given":"Muhammad","family":"Ashfaq","sequence":"additional","affiliation":[{"name":"Department of Physics, University of Sargodha, Sargodha 40100, Pakistan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yasir","family":"Altaf","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Division of Science and Technology, University of Education, Lahore 54770, Pakistan"},{"name":"School of Chemical and Physical Sciences, Victoria University of Wellington, Wellington 6140, New Zealand"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Muhammad Nawaz","family":"Tahir","sequence":"additional","affiliation":[{"name":"Department of Physics, University of Sargodha, Sargodha 40100, Pakistan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2901-7212","authenticated-orcid":false,"given":"Muhammad Fayyaz ur","family":"Rehman","sequence":"additional","affiliation":[{"name":"Institute of Chemistry, Ibn e Sina Block, University of Sargodha, Sargodha 40100, Pakistan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0905-8076","authenticated-orcid":false,"given":"Tariq","family":"Aziz","sequence":"additional","affiliation":[{"name":"Department of Agriculture, University of Ioannina, 471 32 Arta, Greece"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Metab","family":"Alharbi","sequence":"additional","affiliation":[{"name":"Department of Pharmacology and Toxicology, College of Pharmacy, King Saud University, P.O. 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