69323-00-8Relevant academic research and scientific papers
Phenalenyl in a different role: Catalytic activation through the nonbonding molecular orbital
Raha Roy, Sudipta,Nijamudheen,Pariyar, Anand,Ghosh, Anup,Vardhanapu, Pavan K.,Mandal, Prasun K.,Datta, Ayan,Mandal, Swadhin K.
, p. 4307 - 4319 (2014)
We have demonstrated that the nonbonding molecular orbital (NBMO) of the phenalenyl (PLY) cation can be used as a Lewis acid catalyst for different organic transformations. Detailed computational and spectroscopic studies for the aminolysis reaction of ep
Gram-Scale Domino Synthesis in Batch and Flow Mode of Azetidinium Salts
Sivo, Alessandra,Ruta, Vincenzo,Vilé, Gianvito
, p. 14113 - 14120 (2021/09/18)
Azetidinium salts are important motifs in organic synthesis but are difficult to obtain due to extremely long synthetic protocols. Herein, a rapid continuous-flow process for the on-demand synthesis of azetidinium salts is described. In particular, the nu
Fe(III) substituted Wells-Dawson type polyoxometalate: An efficient catalyst for ring opening of epoxides with aromatic amines
Aramesh,Yadollahi,Mirkhani
, p. 37 - 40 (2013/02/26)
Various β-aminoalcohols were prepared by the ring opening reaction of epoxides with aromatic amines in the presence of Fe(III) substituted Wells-Dawson type polyoxometalate, α2-[(n-C4H 9)4N]7P2/
Highly regioselective and efficient synthesis of aminoepoxides by ring closure of aminohalohydrins mediated by KF-Celite
Pace, Vittorio,Hoyos, Pilar,Sinisterra, José Vicente,Alcántara, Andrés R.,Holzer, Wolfgang
supporting information; experimental part, p. 1831 - 1834 (2011/09/16)
The regioselective synthesis of several aminoepoxides has been achieved without observing any trace of azetidinols, which are usually reported as the exclusive reaction products when aminohalohydrins are treated with bases. The use of the mild supported base KF-Celite in refluxing acetonitrile is crucial for modulating the excellent regioselectivity observed. Georg Thieme Verlag Stuttgart . New York.
Simple synthesis of β-acetoxy thiocyanates from oxiranes
Lukowska-Chojnacka, Edyta,Plenkiewicz, Jan
experimental part, p. 1999 - 2006 (2011/06/24)
A convenient and simple method for the preparation of previously unknown β-acetoxy thiocyanates by regioselective ring opening of the corresponding oxiranes with thiocyanate anion followed by acetylation is described. The shorter reaction times, better yields of the products, and easy workup are the advantages of this methodology.
First general route to substituted α-arylamino-α′ chloropropan-2-ones by oxidation of N-protected aminohalohydrins: The importance of disrupting hydrogen bond networks
Pace, Vittorio,Cabrera, Alvaro Cortes,Fernandez, Maria,Sinisterra, Jose V.,Alcantara, Andres R.
scheme or table, p. 3545 - 3555 (2010/12/19)
The presence of a network of intra- and intermolecular hydrogen bonds in β-arylamino alcohols, confirmed by both IR spectroscopy and computer modeling, inhibits their oxidation to the corresponding α-amino ketones. A straightforward protocol, including highly regioselective protection (as carbamates) and subsequent oxidation with Dess-Martin periodinane, affords near quantitative yields of the desired N-protected ketones, which upon mild treatment with iodotrimethylsilane leads to a series of differently functionalized α-arylamino-α′-chloro ketones. Georg Thieme Verlag Stuttgart.
Synthesis, Src kinase inhibitory and anticancer activities of 1-substituted 3-(N-alkyl-N-phenylamino)propane-2-ols
Sharma, Deepti,Sharma, Raman K.,Bhatia, Sumati,Tiwari, Rakesh,Mandal, Deendayal,Lehmann, Jessica,Parang, Keykavous,Olsen, Carl E.,Parmar, Virinder S.,Prasad, Ashok K.
experimental part, p. 1164 - 1172 (2011/11/05)
A series of 3-(N-alkyl-N-phenylamino)propan-2-ol derivatives were synthesized from epichlorohydrine in a multi-step strategy and were evaluated as Src kinase inhibitors. First, epoxy ring opening of epichlorohydrine was carried out in the presence of N-alkylanilines to yield 3-(N-alkyl-N-phenylamino)-1-chloro-propan-2-ol derivatives using Ca(OTf)2 as catalyst based on our previous studies [1]. Second, ring closure was performed under basic conditions to afford N-epoxymethyl N-alkylaniline derivatives. Finally, the epoxide ring opening with four different secondary amines and three nucleobases afforded the final products, i.e., a series of β-amino alcohols. All compounds were screened for their inhibitory activity against Src kinase and anticancer activity on human breast carcinoma cells, BT-20 cell line. Among all compounds, 3-N-methyl-N-phenylamino-1-(pyrrolidin-1-yl)propan-2-ol (13b) exhibited the highest inhibitory potency (IC50 = 66.1 μM) against Src kinase. Structure-activity relationship studies suggested that the incorporation of bulky groups at position 1 and N-substitution with groups larger than methyl moiety, reduced the inhibitory potency of the compound significantly. Compounds 3-(N-ethyl-N-phenylamino-)-1-(4-methylpiperazin-1-yl)propan-2-ol (14c) and 3-(N-ethyl-N-phenylamino)-1-(thymine-1-yl)propan-2-ol (17) were found to inhibit the growth of breast carcinoma cells by approximately 45-49% at concentration of 50 μM.
Al(OTf)3-mediated epoxide ring-opening reactions: Toward piperazine-derived physiologically active products
Williams, D. Bradley G.,Cullen, Adam
supporting information; experimental part, p. 9509 - 9512 (2010/03/04)
(Chemical Equation Presented) Al(OTf)3 is a good catalyst for the ring opening of epoxides, forming β-amino alcohols bearing the piperazine motif. Two different strategies were examined, where the glycidyl ether resided on one-half of the molec
Novel diphenylalkyl piperazine derivatives with high affinities for the dopamine transporter
Kimura, Makoto,Masuda, Tomoko,Yamada, Koji,Mitani, Masaki,Kubota, Nobuo,Kawakatsu, Nobuyuki,Kishii, Kenichi,Inazu, Masato,Kiuchi, Yuji,Oguchi, Katsuji,Namiki, Takayuki
, p. 3953 - 3963 (2007/10/03)
The novel diphenyl piperazine derivatives containing the phenyl substituted aminopropanol moiety, including 1-[4,4-bis(4-fluorophenyl)butyl]-4-[2-hydroxy-3-(phenylamino)propyl]piperazine 1, which were modified at the connective between the diphenyl and piperazine moieties, have been found to be potent dopamine uptake inhibitors. To study the further structure-activity relationship (SAR) of these compounds, a new series was synthesized, with modifications at the 2-hydroxy-3-phenylaminopropyl moiety of 1. The series was evaluated for dopamine transporter (DAT) binding affinity with [3H]GBR12935 in rat striatal membranes. Most of the compounds showed moderate to high DAT binding affinities and some were approximately equivalent in activity to compound 1 or GBR12909 as a dopamine uptake inhibitor, with IC50 values of nanomolar range. The SAR suggested that on exhibiting a potent interaction with the DAT, there is probably a steric limitation around the benzene ring of the phenylamino moiety of 1, allowing only small-sized substituents with the exception of basic moieties at the 4-position. In addition, the SAR at the 3-amino-2-propanol moiety of 1 suggested that either the nitrogen atom with an electron donating substituent or the unsubstituted nitrogen atom and also the hydroxy group are desirable for elicitation of a potent DAT binding affinity.
