- Tetrahydropyrido [3, 4-d] pyrimidine derivative and medical application thereof
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The invention relates to a compound as shown in a general formula (I) or a stereoisomer, a deuterated compound, a solvate, a prodrug, a metabolite, a pharmaceutically acceptable salt or eutectic crystal thereof, an intermediate and a preparation method thereof, and application of the compound in preparation of drugs for treating diseases related to KRas-G12C activity or expression quantity.
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Paragraph 0530-0538
(2021/03/06)
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- Iminium ion-enamine cascade cyclizations: Facile access to structurally diverse azacyclic compounds and natural products
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A one-pot, mild, two-component iminium ion-enamine cascade reaction to construct structurally diverse azacyclic frameworks from l-proline and l-pipecolic acid, and its application to indolizidine and quinolizidine alkaloids and azasteroids, is reported.
- Hanessian, Stephen,Chattopadhyay, Amit Kumar
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p. 232 - 235
(2014/01/23)
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- A systematic study of chiral homoprolinols and their derivatives in the catalysis of enantioselective addition of diethylzinc to aldehydes
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Homoprolinol analogs, a class of optically active γ-amino alcohols, were examined systematically in the enantioselective addition reactions of diethylzinc to aldehydes. By comparison of the results catalyzed by these γ-amino alcohols with those by the β-amino alcohols based on pyrrolidine architecture reported in the literature references, we have observed that the γ-amino alcohols are superior to the corresponding β-amino alcohols when the nitrogen and the oxygen are unsubstituted. Among the homoprolinols we tested, 2b gave the best results (45-88% yields, 44-81% ee) in the addition reactions. To the best of our knowledge, 2b has been noticed as one of the most efficient γ-amino alcohol catalysts based on pyrrolidine framework.
- Liu, Chang-Lu,Wei, Chang-Yong,Wang, Shi-Wen,Peng, Yun-Gui
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experimental part
p. 921 - 928
(2012/06/17)
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- Kinetic deconjugation: A gateway to the synthesis of Xxx-Gly (E)-alkene dipeptide isosteres
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A new method for the preparation of Xxx-Gly (E)-alkene dipeptide isosteres (EADIs), using LDA deprotonation followed by 1 N HCl quench, was explored. The method, named kinetic deconjugation, enabled the synthesis of Tyr-Gly, Gly-Gly, Ser-Gly, Pro-Gly, and
- Proteau-Gagné, Arnaud,Nadon, Jean-Franois,Bernard, Sylvain,Guérin, Brigitte,Gendron, Louis,Dory, Yves L.
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supporting information; experimental part
p. 6603 - 6605
(2012/02/03)
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- Asymmetric synthesis of homoproline derivatives via Rh(I)-catalyzed hydrogenation using chiral bisphosphines as ligands
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It has been demonstrated for the first time that Rh(I)-catalyzed asymmetric hydrogenation of cyclic β-enamino acid derivatives 1 using chiral bisphosphines could be a highly efficient synthetic method for optically active homoproline derivatives. The enantioselectivity and conversion yield were largely dependent upon the chiral ligand. Using the Me-BDPMI forming a seven-membered metal chelate, the N-acetylated β-enamino acid methyl ester 1a was hydrogenated to give optically active homoproline derivative 2a with 100% conversion and 96% ee.
- Zhang, Yong Jian,Park, Jung Hwan,Lee, Sang-Gi
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p. 2209 - 2212
(2007/10/03)
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- CONDENSED HETEROCYCLIC COMPOUNDS AS CALCITONIN AGONISTS
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The present invention relates to novel fused heterocyclic ring system compounds and methods for their use in the treatment and prevention of diseases or conditions which are related to irregular calcification.
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Page/Page column 139
(2010/02/07)
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- Studies towards the preparation of sparteine-like diamines for asymmetric synthesis
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A route for the preparation of sparteine-like diamines starting from naturally occurring amino acids has been explored. Starting from the amino acids (S)-proline and (S)-phenylalanine, two novel sparteine-like diamines 2 and 3 have been prepared. The synthetic route involves Dieckmann condensation followed by a double Mannich reaction to set up the tricyclic structure with control of the relative stereochemistry. During the Dieckmann and Mannich reactions it was found that racemisation occurred either via retro-Michael or retro-Mannich processes. Conditions for preventing racemisation in the Dieckmann reaction were uncovered but it was not possible to prevent racemisation during the double Mannich reaction. Thus, the two novel sparteine-like diamines 2 and 3 have been prepared in racemic form. The Royal Society of Chemistry 1999.
- Harrison, Justin R.,O'Brien, Peter,Porter, David W.,Smith, Neil M.
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p. 3623 - 3631
(2007/10/03)
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- Investigation of the 4-O-alkylamine substituent of non-peptide quinolone GnRH receptor antagonists
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Synthesis and in vitro activity of the enantiomers of quinolone GnRH antagonist (±)-1 are reported. Chiral amino alcohols were prepared from the appropriate cyclic D- or L-amino acids by the Arndt-Eistert homologation followed by reduction of the resulting esters. Incorporation of these pharmacophores was achieved via a novel Mitsunobu alkylation of 4-hydroxyquinolones. The key amine pharmacophore for binding to the rat GnRH receptor was most active in the S-configuration. Ring size was not important for potency with 4, 5, 6, and 7-membered ring amines exhibiting similar potency.
- DeVita, Robert J.,Goulet, Mark T.,Wyvratt, Matthew J.,Fisher, Michael H.,Lo, Jane-L,Yang, Yi Tien,Cheng, Kang,Smith, Roy G.
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p. 2621 - 2624
(2007/10/03)
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- Diastereoselective synthesis of (-)-1-methyl-(3S,4R)-3,4-bis((2S)-N- (tert-butyloxycarbonyl)pyrrolidin-2-yl)-2-pyrrolidinone by an asymmetric Michael reaction
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Beginning with enantiomerically pure L-proline, (-)-1-methyl-(3S,4R)- 3,4-bis((2S)-N-(tert-butyloxycarbonyl)pyrrolidin-2-yl)-2-pyrrolidinone was prepared in diastereomerically pure form. Taking advantage of the chiral induction of the L-proline derivatives, the intermolecular Michael reaction, used to build the pyrrolidinone ring, was carried out stereoselectively.
- Mahboobi, Siavosh,Popp, Alfred,Burgemeister, Thomas,Schollmeyer, Dieter
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p. 2369 - 2376
(2007/10/03)
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- The synthesis of a novel benzodiazocine via an intramolecular Staudinger/aza-Wittig cyclization
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The novel pyrrolobenzodiazocine (1) has been prepared by an intramolecular Staudinger/aza Wittig protocol from the precursor azido aldehyde (2) in a remarkable 93% yield. Aldehyde (2) was prepared by coupling protected homoprolinol with 2-azidobenzoic aci
- O'Neil, Ian A.,Murray, Clare L.,Potter, Andrew J.,Kalindjian, S. Barret
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p. 3609 - 3610
(2007/10/03)
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- LIGAND EFFECTS IN ENANTIOFACE DIFFERENTIATING 1,4 ADDITION TO 1,3 DIPHENYL-2 PROPEN-1 ONE
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The extent of enantiomeric excess in the β-methylation of chalcone by chiral cuprates is shown to depend strongly on small structural modifications of the ligands, all of which are derived from the basic carbon framework of L-prolinol.Enantiomeric excesses up to 88percent have been realised.
- Leyendecker, Francois,Jesser, Francis,Laucher, Dominique
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p. 3513 - 3516
(2007/10/02)
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