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Acid-Catalyzed Synthesis of Isatoic Anhydride-8-Secondary Amides Enables IASA Transformations for Medicinal Chemistry.
Gondi SR, Shaik A, Westover KD. Gondi SR, et al. J Org Chem. 2022 Jan 7;87(1):125-136. doi: 10.1021/acs.joc.1c02036. Epub 2021 Dec 28. J Org Chem. 2022. PMID: 34962124 Free PMC article.
Here, we report an inexpensive, flexible, and scalable method for the one-pot synthesis of substituted quinazolin-dione-N-3-alkyls (isomers of isatoic-8-secondary amides (IASAs)) from isatin that take advantage of in situ capture of imidic acid under acidic conditio …
Here, we report an inexpensive, flexible, and scalable method for the one-pot synthesis of substituted quinazolin-dione-N-3-alkyls (isomers …
A biotin-conjugated pyridine-based isatoic anhydride, a selective room temperature RNA-acylating agent for the nucleic acid separation.
Ursuegui S, Yougnia R, Moutin S, Burr A, Fossey C, Cailly T, Laayoun A, Laurent A, Fabis F. Ursuegui S, et al. Org Biomol Chem. 2015 Mar 28;13(12):3625-32. doi: 10.1039/c4ob02636e. Org Biomol Chem. 2015. PMID: 25671759
Isatoic anhydride derivatives, including a biotin and a disulfide linker were specifically designed for nucleic acid separation. 2'-OH selective RNA acylation, capture of biotinylated RNA adducts by streptavidin-coated magnetic beads and disulfide chemical cl …
Isatoic anhydride derivatives, including a biotin and a disulfide linker were specifically designed for nucleic acid se …
Isatoic anhydrides as novel inhibitors of monoamine oxidase.
Hitge R, Petzer A, Petzer JP. Hitge R, et al. Bioorg Med Chem. 2022 Nov 1;73:117030. doi: 10.1016/j.bmc.2022.117030. Epub 2022 Sep 23. Bioorg Med Chem. 2022. PMID: 36179486
It may be concluded that the isatoic anhydrides represent a new class of MAO inhibitors, while it is interesting to note that very few studies on the pharmacological actions of isatoic anhydrides have been reported. As a secondary aim, the isatoic …
It may be concluded that the isatoic anhydrides represent a new class of MAO inhibitors, while it is interesting to note that …
Green Synthesis of Substituted Anilines and Quinazolines from Isatoic Anhydride-8-amide.
Gondi SR, Bera AK, Westover KD. Gondi SR, et al. Sci Rep. 2019 Oct 3;9(1):14258. doi: 10.1038/s41598-019-50776-y. Sci Rep. 2019. PMID: 31582788 Free PMC article.
Synthetic methods used to generate substituted anilines and quinazolines, both privileged pharmacological structures, are cumbersome, hazardous or, in some cases, unavailable. We developed a straightforward method for making isatoic anhydride-8-amide from isatin-7-c …
Synthetic methods used to generate substituted anilines and quinazolines, both privileged pharmacological structures, are cumbersome, hazard …
Utilization of Aryl(TMP)iodonium Salts for Copper-Catalyzed N-Arylation of Isatoic Anhydrides: An Avenue to Fenamic Acid Derivatives and N,N'-Diarylindazol-3-ones.
Saikia RA, Talukdar K, Pathak D, Sarma B, Thakur AJ. Saikia RA, et al. J Org Chem. 2023 Mar 17;88(6):3567-3581. doi: 10.1021/acs.joc.2c02762. Epub 2023 Feb 24. J Org Chem. 2023. PMID: 36827541
Herein, we report a general method for copper-catalyzed N-arylation of isatoic anhydrides with unsymmetrical iodonium salts at room temperature. ...The methodology offers the broad applicability of both structurally and electronically diverse aryl groups from aryl(T …
Herein, we report a general method for copper-catalyzed N-arylation of isatoic anhydrides with unsymmetrical iodonium salts at …
Quinolines from the cyclocondensation of isatoic anhydride with ethyl acetoacetate: preparation of ethyl 4-hydroxy-2-methylquinoline-3-carboxylate and derivatives.
Jentsch NG, Hume JD, Crull EB, Beauti SM, Pham AH, Pigza JA, Kessl JJ, Donahue MG. Jentsch NG, et al. Beilstein J Org Chem. 2018 Sep 28;14:2529-2536. doi: 10.3762/bjoc.14.229. eCollection 2018. Beilstein J Org Chem. 2018. PMID: 30344776 Free PMC article.
A convenient two-step synthesis of ethyl 4-hydroxy-2-methylquinoline-3-carboxylate derivatives has been developed starting from commercially available 2-aminobenzoic acids. In step 1, the anthranilic acids are smoothly converted to isatoic anhydrides u …
A convenient two-step synthesis of ethyl 4-hydroxy-2-methylquinoline-3-carboxylate derivatives has been developed starting from commercially …
Three-component reaction between isatoic anhydride, amine and meth-yl-subs-tituted furyl-acryl-alde-hydes: crystal structures of 3-benzyl-2-[(E)-2-(5-methylfuran-2-yl)vin-yl]-2,3-di-hydro-quinazolin-4(1H)-one, 3-benzyl-2-[(E)-2-(furan-2-yl)-1-methyl-vin-yl]-2,3-di-hydro-quinazolin-4(1H)-one and 3-(furan-2-ylmeth-yl)-2-[(E)-2-(furan-2-yl)-1-methyl-vin-yl]-2,3-di-hydro-quinazolin-4(1H)-one.
Zaytsev VP, Sorokina EA, Kvyatkovskaya EA, Toze FAA, Mhaldar SN, Dorovatovskii PV, Khrustalev VN. Zaytsev VP, et al. Acta Crystallogr E Crystallogr Commun. 2018 Jul 13;74(Pt 8):1101-1106. doi: 10.1107/S2056989018009982. eCollection 2018 Aug 1. Acta Crystallogr E Crystallogr Commun. 2018. PMID: 30116571 Free PMC article.
Compounds (I), C(22)H(20)N(2)O(2), (II), C(22)H(20)N(2)O(2) and (III), C(20)H(18)N(2)O(3) are the products of three-component reactions between isatoic anhydride, the corresponding amine and 3-(5-methylfuran-2-yl)- or (furan-2-yl)-2-methyl-acryl-aldehyde. ...
Compounds (I), C(22)H(20)N(2)O(2), (II), C(22)H(20)N(2)O(2) and (III), C(20)H(18)N(2)O(3) are the products of three-component reactions betw …
DNA-Compatible Benzotriazinone Formation through Aryl Diazonium Intermediates.
Liu C, Li X, Zhang J, Li Y, Zhang G, Li Y. Liu C, et al. J Org Chem. 2023 Jun 2;88(11):6565-6572. doi: 10.1021/acs.joc.2c02686. Epub 2023 May 22. J Org Chem. 2023. PMID: 37213137
Herein, we reported a synthetic methodology to afford a benzotriazinone core as a drug-like scaffold in a DNA-compatible manner through aryl diazonium intermediates. Starting from DNA-conjugated amines, anthranilic acid or isatoic anhydride building blocks we …
Herein, we reported a synthetic methodology to afford a benzotriazinone core as a drug-like scaffold in a DNA-compatible manner through aryl …
Bronsted Acid-Catalyzed (4 + 3) Cyclization of N, N'-Cyclic Azomethine Imines with Isatoic Anhydrides.
Li C, Wang CS, Li TZ, Mei GJ, Shi F. Li C, et al. Org Lett. 2019 Feb 1;21(3):598-602. doi: 10.1021/acs.orglett.8b03604. Epub 2019 Jan 15. Org Lett. 2019. PMID: 30645136
A Bronsted acid-catalyzed (4 + 3) cyclization of N, N'-cyclic azomethine imines with isatoic anhydrides has been discovered, which constructs seven-membered nitrogenous heterocyclic frameworks with overall high yields (up to 98% yield). ...In addition, this r …
A Bronsted acid-catalyzed (4 + 3) cyclization of N, N'-cyclic azomethine imines with isatoic anhydrides has been discov …
Innately Water-Soluble Isatoic Anhydrides with Modulated Reactivities for RNA SHAPE Analysis.
Fessler AB, Dey A, Finis DS, Fowler AJ, Chakrabarti K, Ogle CA. Fessler AB, et al. Bioconjug Chem. 2020 Mar 18;31(3):884-888. doi: 10.1021/acs.bioconjchem.0c00024. Epub 2020 Feb 17. Bioconjug Chem. 2020. PMID: 32039581
1-Methyl-7-nitroisatoic anhydride (1M7) and 2-methylnicotinic acid imidazolide (NAI) are two of the most commonly applied RNA-SHAPE electrophiles; 1M7 due to its high reactivity and NAI for its solubility and cell permeability. ...This limited solubility has motivat …
1-Methyl-7-nitroisatoic anhydride (1M7) and 2-methylnicotinic acid imidazolide (NAI) are two of the most commonly applied RNA- …
56 results