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Page 1
N-adamantyl-anthranil amide derivatives: New selective ligands for the cannabinoid receptor subtype 2 (CB2R).
Graziano G, Delre P, Carofiglio F, Brea J, Ligresti A, Kostrzewa M, Riganti C, Gioè-Gallo C, Majellaro M, Nicolotti O, Colabufo NA, Abate C, Loza MI, Sotelo E, Mangiatordi GF, Contino M, Stefanachi A, Leonetti F. Graziano G, et al. Eur J Med Chem. 2023 Feb 15;248:115109. doi: 10.1016/j.ejmech.2023.115109. Epub 2023 Jan 13. Eur J Med Chem. 2023. PMID: 36657299
Based on a recent three-arm pharmacophore hypothesis and latest CB2R crystal structures, we designed, synthesized, and evaluated a series of new N-adamantyl-anthranil amide derivatives as CB2R selective ligands. Interestingly, this new class of compounds displayed a high a …
Based on a recent three-arm pharmacophore hypothesis and latest CB2R crystal structures, we designed, synthesized, and evaluated a series of …
Anthranil: An Aminating Reagent Leading to Bifunctionality for Both C(sp(3) )-H and C(sp(2) )-H under Rhodium(III) Catalysis.
Yu S, Tang G, Li Y, Zhou X, Lan Y, Li X. Yu S, et al. Angew Chem Int Ed Engl. 2016 Jul 18;55(30):8696-700. doi: 10.1002/anie.201602224. Epub 2016 Apr 28. Angew Chem Int Ed Engl. 2016. PMID: 27121133
Previous direct C-H nitrogenation suffered from simple amidation/amination with limited atom-economy and is mostly limited to C(sp(2) )-H substrates. In this work, anthranil was designed as a novel bifunctional aminating reagent for both C(sp(2) )-H and C(sp(3) )-H bonds u …
Previous direct C-H nitrogenation suffered from simple amidation/amination with limited atom-economy and is mostly limited to C(sp(2) )-H su …
Convenient synthesis of N-alkyl-3,1-benzoxazin-2-ones from carbamate protected anthranil aldehydes and ketones via one-step alkylation/alkoxy rearrangement.
Tian G, Jin WL, Qin C, Wang J. Tian G, et al. Org Biomol Chem. 2023 Jul 19;21(28):5757-5761. doi: 10.1039/d3ob00812f. Org Biomol Chem. 2023. PMID: 37404025
A practical and step-economical protocol was developed to prepare N-alkyl-3,1-benzoxazin-2-one derivatives from anthranil aldehydes and ketones via one-step alkylation/alkoxy rearrangement, where three new chemical bonds and one ring were constructed in a single step. ...
A practical and step-economical protocol was developed to prepare N-alkyl-3,1-benzoxazin-2-one derivatives from anthranil aldehydes a …
Diverting Reactive Intermediates Toward Unusual Chemistry: Unexpected Anthranil Products from Davis-Beirut Reaction.
Zhu JS, Son JH, Teuthorn AP, Haddadin MJ, Kurth MJ, Tantillo DJ. Zhu JS, et al. J Org Chem. 2017 Oct 20;82(20):10875-10882. doi: 10.1021/acs.joc.7b01521. Epub 2017 Sep 28. J Org Chem. 2017. PMID: 28922917 Free PMC article.
The discovery of a new variation on the Davis-Beirut reaction is described in which an atypical heterocyclic framework (the anthranil or benzo[c]isoxazole framework) is formed as the result of diversion of a key reactive intermediate away from its expected reactivity-a pot …
The discovery of a new variation on the Davis-Beirut reaction is described in which an atypical heterocyclic framework (the anthranil …
Complexes de l'acide anthranil-diacétique avec des métaux trivalents-II Scandium yttrium et lanthane.
Drâgulescu C, Policec S, Simonescu T. Drâgulescu C, et al. Talanta. 1966 Nov;13(11):1543-8. Talanta. 1966. PMID: 18960037 French.
A spectrophotometric study of the complexes formed between anthranil-N,N-diacetic acid, ANDA, and scandium, yttrium and lanthanum, has led to the development of methods for the determination of these elements. ...
A spectrophotometric study of the complexes formed between anthranil-N,N-diacetic acid, ANDA, and scandium, yttrium and lanthanum, ha …
Regioselective Bronsted Acid-Catalyzed Annulation of Cyclopropane Aldehydes with N'-Aryl Anthranil Hydrazides: Domino Construction of Tetrahydropyrrolo[1,2-a]quinazolin-5(1H)ones.
Singh P, Kaur N, Banerjee P. Singh P, et al. J Org Chem. 2020 Mar 6;85(5):3393-3406. doi: 10.1021/acs.joc.9b03170. Epub 2020 Feb 4. J Org Chem. 2020. PMID: 31958951
A highly regioselective synthesis of tetrahydropyrrolo[1,2-a]quinazolin-5(1H)one derivatives was achieved by reacting cyclopropane aldehydes with N'-aryl anthranil hydrazides in the presence of p-toluene sulfonic acid (PTSA). ...
A highly regioselective synthesis of tetrahydropyrrolo[1,2-a]quinazolin-5(1H)one derivatives was achieved by reacting cyclopropane aldehydes …
Rh-Catalyzed N-O Bond Cleavage of Anthranil: A C-H Amination Reagent for Simultaneous Incorporation of Amine and a Functional Group.
Zou M, Liu J, Tang C, Jiao N. Zou M, et al. Org Lett. 2016 Jun 17;18(12):3030-3. doi: 10.1021/acs.orglett.6b01459. Epub 2016 Jun 7. Org Lett. 2016. PMID: 27268937
A novel Rh(III)-catalyzed C-H bond amination with the simultaneous release of a formyl group at distal positions is realized employing anthranil as a new type of C-H amination reagent. This chemistry provides an efficient protocol for the synthesis of 2-acyl diarylamines, …
A novel Rh(III)-catalyzed C-H bond amination with the simultaneous release of a formyl group at distal positions is realized employing an …
Synthesis of α-Ketoamides via Gold(I) Carbene Intermediates.
Wu ZZ, Adak T, Dietl MC, Wang T, Hu C, Shi H, Krämer P, Rudolph M, Rominger F, Hashmi ASK. Wu ZZ, et al. Org Lett. 2022 Jun 24;24(24):4349-4353. doi: 10.1021/acs.orglett.2c01489. Epub 2022 Jun 14. Org Lett. 2022. PMID: 35699937
Here we report an unprecedented gold-catalyzed 2-fold reaction of a bromoalkyne with anthranils. Hydrolysis of the initial product then directly leads to alpha-ketoamides. ...
Here we report an unprecedented gold-catalyzed 2-fold reaction of a bromoalkyne with anthranils. Hydrolysis of the initial product th …
Gold-Catalyzed Transformation of Ynamides.
Shandilya S, Protim Gogoi M, Dutta S, Sahoo AK. Shandilya S, et al. Chem Rec. 2021 Dec;21(12):4123-4149. doi: 10.1002/tcr.202100159. Epub 2021 Aug 25. Chem Rec. 2021. PMID: 34432929
The ynamides reactivity towards nitrogen-transfer reagents, such as azides, nitrogen ylides, isoxazoles, and anthranils; oxygen atom-transfer reagents, like nitrones, sulfoxides, and pyridine N-oxides; and carbon nucleophiles under gold catalysis are herein uncovered. ...
The ynamides reactivity towards nitrogen-transfer reagents, such as azides, nitrogen ylides, isoxazoles, and anthranils; oxygen atom- …
131 results