60479-64-3Relevant academic research and scientific papers
Iridium-catalyzed asymmetric allylic substitutions with bulky amines/oxidative double bond cleavage - Entry into the reetz synthesis of amino alcohols
Seehafer, Kai,Malakar, Chandi C.,Bender, Markus,Qu, Jianping,Liang, Chen,Helmchen, Günter
, p. 493 - 501 (2016/02/18)
Branched allylic amines were prepared by Ir-catalyzed enantioselective allylic aminations with the bulky N-nucleophiles HN(Boc)2 and HNBn2. The products were transformed into N-protected amino aldehydes, which were either reduced or coupled diastereoselectively with organometallic compounds to give vicinal amino alcohols. A formal synthesis of the neurokinin receptor antagonist (+)-L-733060 was carried out as an application. Ir-catalyzed enantioselective allylic aminations with bulky N-nucleophiles HN(Boc)2 and HNBn2 gave N-protected allylic amines, which were transformed into N-protected chiral amino aldehydes. These are useful chiral building blocks as previously demonstrated by Reetz et al. A formal synthesis of the neurokinin receptor antagonist (+)-L-733060 was carried out as an application.
Stereoselective and regioselective intramolecular Friedel-Crafts reaction of aziridinium ions for synthesis of 4-substituted tetrahydroisoquinolines
Chong, Hyun-Soon,Chen, Yunwei
supporting information, p. 5912 - 5915 (2014/01/06)
Optically active 4-substituted tetrahydroisoquinolines were synthesized via intramolecular Friedel-Crafts (FC) reactions of aziridinium ions in a highly regio- and stereoselective manner. Control experiments suggest the formation and ring-opening of aziri
Synthesis of 15N-labeled vicinal diamines through N-activated chiral aziridines: Tools for the NMR study of platinum-based anticancer compounds
Berger, Gilles,Gelbcke, Michel,Cau?t, Emilie,Luhmer, Michel,Nève, Jean,Dufrasne, Fran?ois
supporting information, p. 545 - 548 (2013/02/23)
A new method for the synthesis of 15N-labeled chiral β-diamines from a common precursor, either optically pure amino acids or anti-β-amino alcohols, is reported. The two diastereomeric series of vicinal diamines are produced through the nucleophilic ring opening of activated chiral aziridines. 15N was introduced by means of [ 15N]-benzylamine, prepared from 15NH4Cl. The final compounds are highly valuable because [1H-15N] NMR is considered a powerful tool for studying the chemical properties of platinum-based complexes.
Diastereoselective synthesis and bioactivity of long-chain anti-2-amino-3-alkanols
Chen, Bi-Shuang,Yang, Long-He,Ye, Jian-Liang,Huang, Tao,Ruan, Yuan-Ping,Fu, Jin,Huang, Pei-Qiang
scheme or table, p. 5480 - 5486 (2011/12/14)
An improved four-step approach for the stereoselective synthesis of long-chain anti-2-amino-3-alkanols is described. Using this method, the syntheses of antiproliferative (antitumoral) compounds, spisulosine (ES-285, 2), clavaminols A and B (3 and 4), the deacetylated products of clavaminols H and N (7 and 8), as well as (2S,3R)-2-aminododecan-3-ol (9) and xestoaminol C (10), have been achieved in excellent diastereoselectivities. In vitro study showed that these compounds induced cell death and dose-dependently inhibited cell proliferation in human glioblastoma cell line SHG-44, indicating the anti-tumor property of this series of compounds.
From rigid cyclic templates to conformationally stabilized acyclic scaffolds. Part II: Acyclic replacements for the (3S)-3-benzylpiperidine in a series of potent CCR3 antagonists
Gardner, Daniel S.,Santella III, Joseph B.,Tebben, Andrew J.,Batt, Douglas G.,Ko, Soo S.,Traeger, Sarah C.,Welch, Patricia K.,Wadman, Eric A.,Davies, Paul,Carter, Percy H.,Duncia, John V.
, p. 586 - 595 (2008/09/17)
Conformational analysis of the 3-benzylpiperidine in CCR3 antagonist clinical candidate 1 (BMS-639623) predicts that the benzylpiperidine may be replaced by acyclic, conformationally stabilized, anti-1,2-disubstituted phenethyl- and phenpropylamines. Ab i
From rigid cyclic templates to conformationally stabilized acyclic scaffolds. Part I: The discovery of CCR3 antagonist development candidate BMS-639623 with picomolar inhibition potency against eosinophil chemotaxis
Santella III, Joseph B.,Gardner, Daniel S.,Yao, Wenqing,Shi, Chongsheng,Reddy, Prabhakar,Tebben, Andrew J.,DeLucca, George V.,Wacker, Dean A.,Watson, Paul S.,Welch, Patricia K.,Wadman, Eric A.,Davies, Paul,Solomon, Kimberly A.,Graden, Dani M.,Yeleswaram, Swamy,Mandlekar, Sandhya,Kariv, Ilona,Decicco, Carl P.,Ko, Soo S.,Carter, Percy H.,Duncia, John V.
, p. 576 - 585 (2008/09/19)
Conformational analysis of trans-1,2-disubstituted cyclohexane CCR3 antagonist 2 revealed that the cyclohexane linker could be replaced by an acyclic syn-α-methyl-β-hydroxypropyl linker. Synthesis and biological evaluation of mono- and disubstituted propyl linkers support this conformational correlation. It was also found that the α-methyl group to the urea lowered protein binding and that the β-hydroxyl group lowered affinity for CYP2D6. Ab initio calculations show that the α-methyl group governs the spatial orientation of three key functionalities within the molecule. α-Methyl-β-hydroxypropyl urea 31 with a chemotaxis IC50 = 38 pM for eosinophils was chosen to enter clinical development for the treatment of asthma.
4,5-Dialkylsubstituted 2-imino-1,3-thiazolidine derivatives as potent inducible nitric oxide synthase inhibitors
Ueda, Shigeo,Terauchi, Hideo,Yano, Akihiro,Matsumoto, Masashi,Kubo, Taeko,Kyoya, Yoko,Suzuki, Kenji,Ido, Motoharu,Kawasaki, Motoji
, p. 4101 - 4116 (2007/10/03)
In the course of our search for selective iNOS inhibitors, we have previously reported that 2-imino-1,3-oxazolidine derivatives (1) and 2-aminothiazole derivatives (2) are selective iNOS inhibitors. In order to find more potent iNOS inhibitors, we focused
The power of visual imagery in drug design. Isopavines as a new class of morphinomimetics and their human opioid receptor binding activity
Hanessian, Stephen,Parthasarathy, Saravanan,Mauduit, Marc,Payza, Kemal
, p. 34 - 48 (2007/10/03)
The importance of visual imagery and relational thinking manifests itself in a heuristic approach to the design and synthesis of potential morphinomimetics as agonists of the human-receptor. The well-known class of alkaloids represented by the isopavine n
Stereoselective synthesis of the four stereoisomers of 4-(N,N- dibenzylamino)-2,2-dimethyl-3-hydroxypentanenitrile
Moriarty, Robert M.,Tao, Anping,Tuladhar, Sudersan M.
, p. 3227 - 3234 (2007/10/03)
The title compounds 1(a,b) and 1(c,d) were synthesized by (i) non- chelation controlled sodium borohydride reduction of their corresponding α- N,N-dibenzylaminoketones and (ii) the Aldol-type condensation of optically pure N,N-dibenzylaminoaldehydes with the lithium derivative of isobutyronitrile, respectively. Attempted inversion of configurations of these secondary alcohols using the Moriarty method yielded 4 -chloro-3 -N,N- dibenzylaminonitrile via an aziridinium ion intermediate instead of the expected inverted alcohols.
