Publication: Unexpected synthesis of 3-imino-2-(pyrrol-2-yl) isatogen derivatives affords facile access to a 2-pyrrolyl isatogen
| dc.contributor.author | Kirk N.S. | |
| dc.contributor.author | Sansom G.N. | |
| dc.contributor.author | Sudta P. | |
| dc.contributor.author | Suksamrarn S. | |
| dc.contributor.author | Willis A.C. | |
| dc.contributor.author | Bremner J.B. | |
| dc.contributor.author | Kelso M.J. | |
| dc.date.accessioned | 2021-04-05T03:22:59Z | |
| dc.date.available | 2021-04-05T03:22:59Z | |
| dc.date.issued | 2017 | |
| dc.date.issuedBE | 2560 | |
| dc.description.abstract | 2-Aryl isatogens and their 3-imino derivatives have been extensively studied but to date there have been no reported variants carrying pyrrolyl substituents at the 2-position. This study describes the unexpected synthesis of two novel 3-imino-2-(pyrrol-2-yl) isatogen derivatives upon attempted amide couplings with (E)- or (Z)-3-(3,5-dimethyl-1H-pyrrol-2-yl)-2-(2-nitrophenyl)acrylic acids and p-phenylenediamines in the presence of uronium-based coupling reagents. Imine hydrolysis of one derivative under mild acid conditions afforded a 2-pyrrolyl isatogen in high yield. The compound showed potent in vitro antiplasmodial activity against Plasmodium falciparum. © 2017, Copyright © Taylor & Francis Group, LLC. | |
| dc.format.mimetype | application/pdf | |
| dc.identifier.citation | Synthetic Communications. Vol 47, No.1 (2017), p.62-67 | |
| dc.identifier.doi | 10.1080/00397911.2016.1249290 | |
| dc.identifier.issn | 397911 | |
| dc.identifier.other | 2-s2.0-85001022754 | |
| dc.identifier.uri | https://hdl.handle.net/20.500.14740/4667 | |
| dc.rights.holder | Scopus | |
| dc.subject.other | Amide | |
| dc.subject.other | Antiprotozoal agent | |
| dc.subject.other | Imine | |
| dc.subject.other | Isatogen derivative | |
| dc.subject.other | Unclassified drug | |
| dc.subject.other | Antiprotozoal activity | |
| dc.subject.other | Article | |
| dc.subject.other | Crystal structure | |
| dc.subject.other | Drug synthesis | |
| dc.subject.other | Hydrogen bond | |
| dc.subject.other | Hydrolysis | |
| dc.subject.other | In vitro study | |
| dc.subject.other | Nonhuman | |
| dc.subject.other | Plasmodium falciparum | |
| dc.title | Unexpected synthesis of 3-imino-2-(pyrrol-2-yl) isatogen derivatives affords facile access to a 2-pyrrolyl isatogen | |
| dc.type | Article | |
| dspace.entity.type | Publication | |
| swu.datasource.scopus | https://www.scopus.com/inward/record.uri?eid=2-s2.0-85001022754&doi=10.1080%2f00397911.2016.1249290&partnerID=40&md5=7949854671a017e164167bc9082ccf60 |