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Unknown field was ignored: [1,2-a]
Page 1
Assembly of 1,2,3,4-Tetrahydropyrrolo[1,2-a]pyrazines via the Domino Reaction of 2-Imidazolines and Terminal Electron-Deficient Alkynes.
Golantsov NE, Golubenkova AS, Festa AA, Varlamov AV, Voskressensky LG. Golantsov NE, et al. J Org Chem. 2022 Mar 4;87(5):3242-3253. doi: 10.1021/acs.joc.1c02930. Epub 2022 Jan 20. J Org Chem. 2022. PMID: 35049314
The transformation of 2-imidazolines into 1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazines has been realized. A pseudo-three-component reaction of 2-imidazolines with terminal electron-deficient alkynes (2 equiv) first generates imidazolidines, …
The transformation of 2-imidazolines into 1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazines has been reali …
One-pot synthesis of novel 1-(1H-tetrazol-5-yl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine derivatives via an Ugi-azide 4CR process.
Ghandi M, Salahi S, Taheri A, Abbasi A. Ghandi M, et al. Mol Divers. 2018 May;22(2):291-303. doi: 10.1007/s11030-017-9801-4. Epub 2017 Dec 11. Mol Divers. 2018. PMID: 29230611
A facile one-pot method has been developed for the synthesis of novel pyrrolo[2,1-a]pyrazine scaffolds. A variety of 1-(1H-tetrazol-5-yl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine derivatives were obtained in moderate to high yields …
A facile one-pot method has been developed for the synthesis of novel pyrrolo[2,1-a]pyrazine scaffolds. A variety of 1-(1H-tetrazol-5 …
Novel, highly potent aldose reductase inhibitors: (R)-(-)-2-(4-bromo-2-fluorobenzyl)-1,2,3,4- tetrahydropyrrolo[1,2-a]pyrazine -4-spiro-3'-pyrrolidine-1,2',3,5'-tetrone (AS-3201) and its congeners.
Negoro T, Murata M, Ueda S, Fujitani B, Ono Y, Kuromiya A, Komiya M, Suzuki K, Matsumoto J. Negoro T, et al. J Med Chem. 1998 Oct 8;41(21):4118-29. doi: 10.1021/jm9802968. J Med Chem. 1998. PMID: 9767647
Of these compounds, spirosuccinimide-fused tetrahydropyrrolo[1, 2-a]pyrazine-1,3-dione derivatives showed significantly potent AR inhibitory activity. In the in vivo activity of these derivatives, 2-(4-bromo-2-fluorobenzyl)-1,2,3,4-tetrahydro …
Of these compounds, spirosuccinimide-fused tetrahydropyrrolo[1, 2-a]pyrazine-1,3-dione derivatives showed significantly potent AR inh …
Direct synthesis of chiral 1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazines via a catalytic asymmetric intramolecular aza-Friedel-Crafts reaction.
He Y, Lin M, Li Z, Liang X, Li G, Antilla JC. He Y, et al. Org Lett. 2011 Sep 2;13(17):4490-3. doi: 10.1021/ol2018328. Epub 2011 Aug 11. Org Lett. 2011. PMID: 21834569
The direct asymmetric intramolecular aza-Friedel-Crafts reaction of N-aminoethylpyrroles with aldehydes catalyzed by a chiral phosphoric acid represents the first efficient method for the preparation of medicinally interesting chiral 1,2,3,4-tetrahy …
The direct asymmetric intramolecular aza-Friedel-Crafts reaction of N-aminoethylpyrroles with aldehydes catalyzed by a chiral phosphoric aci …
Novel routes to 1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazines and 5,6,9,10,11,11a-hexahydro-8H-pyrido[1,2-a]pyrrolo[2,1-c]pyrazines.
Katritzky AR, Jain R, Xu YJ, Steel PJ. Katritzky AR, et al. J Org Chem. 2002 Nov 15;67(23):8220-3. doi: 10.1021/jo020371t. J Org Chem. 2002. PMID: 12423155
Subsequent nucleophilic substitutions of the benzotriazole group in 2 and 6 with Grignard reagents, sodium cyanide, and sodium borohydride gave 1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazines 3a-e, 4, 5 and 5,6,9,10,11,11a-hexahydro-8H-pyrido[1 …
Subsequent nucleophilic substitutions of the benzotriazole group in 2 and 6 with Grignard reagents, sodium cyanide, and sodium borohydride g …
Histone deacetylase inhibitors derived from 1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine and related heterocycles selective for the HDAC6 isoform.
Blackburn C, Barrett C, Brunson M, Chin J, England D, Garcia K, Gigstad K, Gould A, Gutierrez J, Hoar K, Rowland RS, Tsu C, Ringeling J, Wager K, Xu H. Blackburn C, et al. Bioorg Med Chem Lett. 2014 Dec 1;24(23):5450-4. doi: 10.1016/j.bmcl.2014.10.022. Bioorg Med Chem Lett. 2014. PMID: 25454270
Acyl derivatives of 4-(aminomethyl)-N-hydroxybenzamide are potent sub-type selective HDAC6 inhibitors. Constrained heterocyclic analogs based on 1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine show further enhanced HDAC6 selectivity and inhibito …
Acyl derivatives of 4-(aminomethyl)-N-hydroxybenzamide are potent sub-type selective HDAC6 inhibitors. Constrained heterocyclic analogs base …
Quantitative structure and aldose reductase inhibitory activity relationship of 1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-4-spiro-3'-pyrrolidine-1,2',3,5'-tetrone derivatives.
Ko K, Won Y. Ko K, et al. Bioorg Med Chem. 2005 Mar 1;13(5):1445-52. doi: 10.1016/j.bmc.2004.12.034. Bioorg Med Chem. 2005. PMID: 15698760
We investigate the quantitative structure-activity relationship of spirosuccinimide-fused tetrahydropyrrolo[1,2-a]pyrazine-1,3-dione derivatives acting as aldose reductase inhibitors, which contain a chiral center. ...
We investigate the quantitative structure-activity relationship of spirosuccinimide-fused tetrahydropyrrolo[1,2-a]pyrazine-1,3-dione …
[2-(2'-hydroxy 2'-substituted) ethyl-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazines--a novel group of substances with anti-arrhythmia activity].
Filippova OV, Kryzhanovskiĭ SA, Peresada VP, Likhosherstov AM, Vititnova MB, Kaverina NV, Reznikov KM. Filippova OV, et al. Eksp Klin Farmakol. 2003 May-Jun;66(3):21-5. Eksp Klin Farmakol. 2003. PMID: 12924227 Russian.
The antiarrhythmic activity and acute toxicity of a series of 2-(2'-hydroxy-2'-substituted) ethyl-1,2,3,4-tetrahydropyrrolo[1,2- a]pyrazines were studied. Two most promising compounds (PV-168 PV-174) are characterized by a high antiarrhyt …
The antiarrhythmic activity and acute toxicity of a series of 2-(2'-hydroxy-2'-substituted) ethyl-1,2,3,4-tet …
Iridium-catalyzed asymmetric hydrogenation of pyrrolo[1,2-a]pyrazinium salts.
Huang WX, Yu CB, Shi L, Zhou YG. Huang WX, et al. Org Lett. 2014 Jun 20;16(12):3324-7. doi: 10.1021/ol5013313. Epub 2014 Jun 9. Org Lett. 2014. PMID: 24911796
Highly enantioselective iridium-catalyzed hydrogenation of pyrrolo[1,2-a]pyrazinium salts has been achieved, providing a direct access to chiral 1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine derivatives with up to 95% ee. ...
Highly enantioselective iridium-catalyzed hydrogenation of pyrrolo[1,2-a]pyrazinium salts has been achieved, providing a direct access to ch …
Stereospecific interaction of a novel spirosuccinimide type aldose reductase inhibitor, AS-3201, with aldose reductase.
Kurono M, Fujiwara I, Yoshida K. Kurono M, et al. Biochemistry. 2001 Jul 27;40(28):8216-26. doi: 10.1021/bi0102813. Biochemistry. 2001. PMID: 11444967
Aldose reductase (AR) is an NADPH-dependent enzyme implicated in diabetic complications. AS-3201 [(R)-(-)-2-(4-bromo-2-fluorobenzyl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-4-spiro-3'-pyrrolidine-1,2',3,5'-tetrone] is a structurally nove …
Aldose reductase (AR) is an NADPH-dependent enzyme implicated in diabetic complications. AS-3201 [(R)-(-)-2-(4-bromo-2-fluorobenzyl)-1 …
12 results