1541-25-9Relevant academic research and scientific papers
Synthesis and Enzymatic Evaluation of Conformationally Defined Carnitine Analogs
Brouillette, Wayne J.,Saeed, Ashraf,Abuelyaman, Ahmed,Hutchison, Tracy L.,Wolkowicz, Paul E.,McMillin, Jeanie B.
, p. 4297 - 4303 (1994)
Carnitine (1, 3-hydroxy-4-trimethylammoniobutyrate) is essential as a donor and acceptor of acyl groups in cellular metabolism.The major solution conformation of carnitine about C3-C4 contains the gauche reletionship between the trimethylammonium and hydr
Asymmetric synthesis of primary amines catalyzed by thermotolerant fungal reductive aminases
Cosgrove, Sebastian C.,Grogan, Gideon,Mangas-Sanchez, Juan,Marshall, James R.,Palmer, Ryan B.,Ramsden, Jeremy I.,Sharma, Mahima,Thorpe, Thomas W.,Turner, Nicholas J.
, p. 5052 - 5057 (2020/06/09)
Chiral primary amines are important intermediates in the synthesis of pharmaceutical compounds. Fungal reductive aminases (RedAms) are NADPH-dependent dehydrogenases that catalyse reductive amination of a range of ketones with short-chain primary amines supplied in an equimolar ratio to give corresponding secondary amines. Herein we describe structural and biochemical characterisation as well as synthetic applications of two RedAms fromNeosartoryaspp. (NfRedAm andNfisRedAm) that display a distinctive activity amongst fungal RedAms, namely a superior ability to use ammonia as the amine partner. Using these enzymes, we demonstrate the synthesis of a broad range of primary amines, with conversions up to >97% and excellent enantiomeric excess. Temperature dependent studies showed that these homologues also possess greater thermal stability compared to other enzymes within this family. Their synthetic applicability is further demonstrated by the production of several primary and secondary amines with turnover numbers (TN) up to 14 000 as well as continous flow reactions, obtaining chiral amines such as (R)-2-aminohexane in space time yields up to 8.1 g L?1h?1. The remarkable features ofNfRedAmand NfisRedAm highlight their potential for wider synthetic application as well as expanding the biocatalytic toolbox available for chiral amine synthesis.
Cobalt-catalyzed cyclization with the introduction of cyano, acyl and aminoalkyl groups
Hori, Hiroto,Arai, Shigeru,Nishida, Atsushi
supporting information, p. 4783 - 4788 (2019/05/24)
An efficient synthesis of carbo-and heterocycles using CC, CO and CN bonds under cobalt catalysis is described. The substituents on olefins are key for controlling the regio-and chemoselectivity in the initial hydrogen atom transfer step and quaternary carbons are efficiently constructed under mild conditions. Cyclopropane cleavage and tandem cyclization give highly functionalized bicyclic skeletons in a single operation.
Discovery of Novel 1-Cyclopentenyl-3-phenylureas as Selective, Brain Penetrant, and Orally Bioavailable CXCR2 Antagonists
Lu, Hongfu,Yang, Ting,Xu, Zhongmiao,Lin, Xichen,Ding, Qian,Zhang, Yueting,Cai, Xin,Dong, Kelly,Gong, Sophie,Zhang, Wei,Patel, Metul,Copley, Royston C. B.,Xiang, Jianing,Guan, Xiaoming,Wren, Paul,Ren, Feng
supporting information, p. 2518 - 2532 (2018/03/26)
CXCR2 has emerged as a therapeutic target for not only peripheral inflammatory diseases but also neurological abnormalities in the central nervous system (CNS). Herein, we describe the discovery of a novel 1-cyclopentenyl-3-phenylurea series as potent and CNS penetrant CXCR2 antagonists. Extensive SAR studies, wherein molecules' property forecast index (PFI) was carefully optimized for overall balanced developability profiles, led to the discovery of the advanced lead compound 68 with a desirable PFI. Compound 68 demonstrated good in vitro pharmacology with excellent selectivity over CXCR1 and other chemokine receptors. Rat and dog pharmacokinetics (PK) revealed good oral bioavailability, high oral exposure, and desirable elimination half-life of the compound in both species. In addition, the compound demonstrated dose-dependent efficacy in the in vivo pharmacology neutrophil infiltration "air pouch" model in rodents after oral administration. Further, compound 68 is a CNS penetrant molecule with high unbound fraction in brain tissue.
Platinum-catalyzed direct amination of allylic alcohols with aqueous ammonia: Selective synthesis of primary allylamines
Das, Kalpataru,Shibuya, Ryozo,Nakahara, Yasuhito,Germain, Nicolas,Ohshima, Takashi,Mashima, Kazushi
supporting information; experimental part, p. 150 - 154 (2012/02/16)
Direct amination of unactivated allylic alcohols with aqueous ammonia was catalyzed by a Pt/phosphine complex to give the corresponding allylamines along with water as the sole by-product. Under optimized reaction conditions, primary allylamines were obtained as major products with excellent monoallylation selectivity. cod=1,5-cyclooctadiene.
cis- and trans-Stereoselective Epoxidation of N-Protected 2-Cyclohexen-1-ylamines
O'Brien, Peter,Childs, Amanda C.,Ensor, Gareth J.,Hill, Cheryl L.,Kirby, Jonathan P.,Dearden, Michael J.,Oxenford, Sally J.,Rosser, Clare M.
, p. 4955 - 4957 (2007/10/03)
(Equation Presented) The first systematic study of the cis and trans stereoselectivity in the m-CPBA epoxidation of N-protected cyclic allylic amines has been completed. Mono-N-protected systems gave epoxides with cis stereochemistry (amides are better ci
Direct amination of olefins through sequential triazolinedione ene reaction and carbanion-assisted cleavage of the N-N urazole bond
Adam, Waldemar,Pastor, Aurelia,Wirth, Thomas
, p. 1295 - 1297 (2007/10/03)
(formula presented) Allylic amines 5 are obtained in 30-55% overall yields by the base-catalyzed hydrolysis of trialkylated allylic urazoles 3; the latter are prepared by the TAD ene reaction of the appropriate olefin and further N-alkylation with α-bromo
Intramolecular Diels-Alder reaction of cyclenic trienes: Stereoselectivity and NMR structure determination
Blond, Alain,Platzer, Nicole,Guy, Alain,Dhotel, Helene,Serva, Laurence
, p. 283 - 293 (2007/10/03)
A series of trienes possessing an internally cyclenic dienophilic group undergo thermal intramolecular DielsAlder (IMDA) reaction with high selectivity for the cis-fused products. A concentrated solution of LIC1O4 in diethyl ether catalyzes the IMDA reaction of cyclenic nitrotrienes, giving rise to the irans-fused compounds. The stereochcmical outcome of these various processes are rationalized in terms of a minimization of the steric interactions between the ring and the chain on the one hand and the endo-stabilization from the nitro group on the other. The structures of the cycloadducts have been carefully determined by NMR 1H and 13C spectroscopy: dipolar interactions, detected via nuclear Overhauser effects, and criteria based on scalar coupling and moreover on chemical shifts have been employed. Conformational preferences were observed. Elsevier,.
ALKYL AND ARYL ISOTHIOCYANATES AS MASKED PRIMARY AMINES
Cho, Cheon-Gyu,Posner, Gary H.
, p. 3599 - 3602 (2007/10/02)
Primary and secondary (but not tertiary) alkyl as well as aryl isothiocyanates react rapidly with 4-methyl-1,2-benzenedithiol (1) in methanol at room temperature, releasing the corresponding amines in good yields.This mild and simple procedure for unmasking amines proceeds chemospecifically with isothiocyanates even in the presence of such normally electrophilic and reactive functionalities as carboxylate ester and N-alkylphthalimide.
