6216-63-3Relevant articles and documents
Synthesis of pyrrolizidines via Copper(I) catalyzed radical atom transfer cyclization
Seijas,Vazquez-Tato,Castedo,Estevez,Onega,Ruiz
, p. 1637 - 1642 (1992)
Trachelanthamidine and pseudoheliotridane are synthesized from (2S)-N-trichloroacetyl-2-vinylpyrrolidine (5) by a 5-exo-trig radical cyclization. The intermediate radical is generated heating 5 in a sealed tube (CH3CN/160°C) using CuCl as catal
Chemoenzymatic synthesis and inhibitory activities of hyacinthacines A 1 and A2 stereoisomers
Calveras, Jordi,Casas, Josefina,Parella, Teodor,Joglar, Jesus,Clapes, Pere
, p. 1661 - 1666 (2007)
A novel straightforward chemoenzymatic procedure for the synthesis of hyacinthacine stereoisomers based on the aldol addition of dihydroxyacetone phosphate (DHAP) to N-Cbz-prolinal under catalysis by L-rhamnulose 1-phosphate aldolase from E. coli is prese
Synthesis and absolute configuration of 2-(12'-aminotridecyl)-pyrrolidine, a defensive alkaloid from the Mexican bean beetle, Epilachna varivestis
Shi,Attygalle,Xu,Ahmad,Meinwald
, p. 6859 - 6868 (1996)
The synthesis of 2-(12'-aminotridecyl)-pyrrolidine (1), a defensive alkaloid recently isolated from the Mexican bean beetle, Epilachna varivestis, is described. The (2S,12'R) configuration is assigned to this alkaloid by comparing the 1H NMR spectrum of its (S)-MTPA derivative with that of (R)- and (S)-MTPA [α-methoxy-α-(trifluoromethyl)phenylacetyl] derivatives of the synthetic sample. These results suggest that the seventeen carbon skeleton of 1 is acetate rather than proline derived.
Discovery of substituted 3H-pyrido[2,3-d]pyrimidin-4-ones as potent, biased, and orally bioavailable sst2 agonist
Betz, Stephen F.,Chen, Zhiyong,Kusnetzow, Ana Karin,Nguyen, Julie,Rico-Bautista, Elizabeth,Struthers, R. Scott,Tan, Hannah,Zhao, Jian,Zhu, Yunfei
supporting information, (2020/08/26)
The discovery of a novel 3H-pyrido[2,3-d]pyrimidin-4-one series as potent and biased sst2 agonists is described. This class of molecules exhibits excellent sst2 potency and selectivity against sst1, sst3, and sst5 receptors, and they are significantly more potent at inhibiting cAMP production than inducing internalization. The orally bioavailable 6-(3-chloro-5-methylphenyl)-3-(3-fluoro-5-hydroxyphenyl)-5-({methyl[(2S)-pyrrolidin-2-ylmethyl]amino}methyl)-3H,4H-pyrido[2,3-d]pyrimidin-4-one (36) also suppresses GH secretion in GHRH-challenged rats in a dose-dependent manner.
Efficient synthesis of methyl (S)-4-(1-methylpyrrolidin-2-YL)-3-oxobutanoate as the key intermediate for tropane alkaloid biosynthesis with optically acitve form
Katakam, Nanda Kumar,Seifert, Cole W.,D'Auria, John,Li, Guigen
, p. 604 - 613 (2019/08/01)
Methyl (S)-4-(1-methylpyrrolidin-2-yl)-3-oxobutanoate has been synthesized for enzymatic studies on cyclization enzymes during cocaine biosynthesis in Erythroxylum coca plants. During the present new synthesis, L-proline was first protected with Cbz group and reduced to chiral amino alcohol, which were then followed by Swern oxidation, Wittig reaction and decarboxylative condensation. At the last step, N-methylamino acid precursor was treated with 1,1'-carbonyldiimidazole followed by reacting with methyl potassium malonate to give the 3-oxobutanoate in 54% overall yield. This new strategy has proven to avoid obvious racemization of the L-proline chiral center during the synthesis. In addition, six of the eight synthesis steps were performed via GAP chemistry/technology without the use of column chromatography for purification.
Synthesis of Nα-Z protected amino alkyl triazole acids and their application to neo-glycopeptides synthesis
Madhu, Chilakapati,Panguluri, Nageswara Rao,Sureshbabu, Vommina V.
, p. 858 - 864 (2014/08/05)
The synthesis of triazole linked glycopeptides employing 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) mediated coupling of Z-protected triazole acids with glycosyl amines and amino acid esters is described. The coupling proceeded smoothly at room temperat
Syntheses of chiral ferrocenophanes and their application to asymmetric catalysis
Zhang, Qiying,Cui, Xiuling,Chen, Lianmei,Liu, Haitao,Wu, Yangjie
, p. 7823 - 7829 (2015/01/16)
N-Substituted 2-aza-[3]-ferrocenophanes were easily synthesized from 1,1′-ferrocenedicarbaldehyde and aliphatic amines in high yields. One of the ferrocenophanes served as a ligand for the copper-catalyzed oxidative coupling of 2-naphthol derivatives to give the products in good yields with up to 92% ee, and it also efficiently catalyzed the asymmetric Michael addition reaction as an organocatalyst.
Synthesis of (R)-norbgugaine and its potential as quorum sensing inhibitor against Pseudomonas aeruginosa
Majik, Mahesh S.,Naik, Deepak,Bhat, Chinmay,Tilve, Santosh,Tilvi, Supriya,D'Souza, Lisette
, p. 2353 - 2356 (2013/05/09)
(R)-Bgugaine is a natural pyrrolidine alkaloid from Arisarum vulgare, which shows antifungal and antibacterial activity. In this Letter, we have accomplished the simple synthesis of norbgugaine (demethylated form of natural bgugaine) employing Wittig olefination and cat. hydrogenation as the key steps and its biological studies are reported for the first time. The synthesized norbgugaine was evaluated for inhibition of quorum sensing mediated virulence factors (motility, biofilm formation, pyocyanin pigmentation, rhamnolipid production and LasA protease) in Pseudomonas aeruginosa wherein swarming motility is reduced by 95%, and biofilm formation by 83%.
Henry-Nef reaction: A practical and versatile chiral pool route to 2-substituted pyrrolidine and piperidine alkaloids
Bhat, Chinmay,Tilve, Santosh G.
, p. 6129 - 6143 (2013/07/27)
The paper describes the synergistic protocol developed by combinatorial Henry and Nef reaction for the synthesis of 2-substituted pyrrolidine and piperidine alkaloids containing 1,3-aminoketone and 1,3-amino alcohol units. The utility of the protocol is demonstrated by asymmetric synthesis of 12 natural products of which asymmetric synthesis of (-)-N-methylpelletierine is presented for the first time. The one-carbon homologation described also provides an alternate route for the synthesis of key intermediates homoprolinol and homopipecolinol used as synthetic precursors for several alkaloids and construction of β-amino acids from α-amino acids.
Interfacial cavity filling to optimize CD4-mimetic miniprotein interactions with HIV-1 surface glycoprotein
Morellato-Castillo, Laurence,Acharya, Priyamvada,Combes, Olivier,Michiels, Johan,Descours, Anne,Ramos, Oscar H. P.,Yang, Yongping,Vanham, Guido,Ari?n, Kevin K.,Kwong, Peter D.,Martin, Lo?c,Kessler, Pascal
, p. 5033 - 5047 (2013/07/26)
Ligand affinities can be optimized by interfacial cavity filling. A hollow (Phe43 cavity) between HIV-1 surface glycoprotein (gp120) and cluster of differentiation 4 (CD4) receptor extends beyond residue phenylalanine 43 of CD4 and cannot be fully accessed by natural amino acids. To increase HIV-1 gp120 affinity for a family of CD4-mimetic miniproteins (miniCD4s), we targeted the gp120 Phe43 cavity with 11 non-natural phenylalanine derivatives, introduced into a miniCD4 named M48 (1). The best derivative, named M48U12 (13), bound HIV-1 YU2 gp120 with 8 pM affinity and showed potent HIV-1 neutralization. It contained a methylcyclohexyl derivative of 4-aminophenylalanine, and its cocrystal structure with gp120 revealed the cyclohexane ring buried within the gp120 hydrophobic core but able to assume multiple orientations in the binding pocket, and the aniline nitrogen potentially providing a focus for further improvement. Altogether, the results provide a framework for filling the interfacial Phe43 cavity to enhance miniCD4 affinity.
