17422-12-7Relevant articles and documents
Antitubercular agents. Part 2: New thiolactomycin analogues active against Mycobacterium tuberculosis
Kamal, Ahmed,Ali Shaik, Ahmad,Sinha, Rakesh,Yadav,Arora, Sudarshan K.
, p. 1927 - 1929 (2005)
Structurally modified analogues of naturally occurring antibiotic thiolactomycin, substituted at 4-position of the thiolactone ring have been prepared and evaluated for their antitubercular activity. Some of the compounds have exhibited potential activity against Mycobacterium tuberculosis.
Origins of stereoselectivity in the α-alkylation of chiral hydrazones
Krenske, Elizabeth H.,Houk,Lim, Daniel,Wengryniuk, Sarah E.,Coltart, Don M.
, p. 8578 - 8584 (2010)
Density functional theory calculations and experiment reveal the origin of stereoselectivity in the deprotonation-alkylation of chiral N-amino cyclic carbamate (ACC) hydrazones. When the ACC is a rigid, camphor-derived carbamate, the two conformations of the azaenolate intermediate differ in energy due to conformational effects within the oxazolidinone ring and steric interactions between the ACC and the azaenolate. An electrophile adds selectively to the less-hindered π-face of the azaenolate. Although it was earlier reported that use of ACC auxiliaries led to α-alkylated ketones with er values of 82:18 to 98:2, B3LYP calculations predict higher stereoselectivity. Direct measurement of the dr of an alkylated hydrazone prior to removal of the auxiliary confirms this prediction; the removal of the auxiliary under the reported conditions can compromise the overall stereoselectivity of the process.
Chemoenzymatic synthesis of (5S)- and (5R)-hydroxymethyl-3,5-dimethyl-4-(methoxymethoxy)-5H-thiophen-2-one: a precursor of thiolactomycin and determination of its absolute configuration
Kamal, Ahmed,Shaik, Ahmad Ali,Azeeza, Shaik,Malik, M. Shaheer,Sandbhor, Mahendra
, p. 2890 - 2895 (2006)
A convenient enantioselective synthesis of (5S)- and (5R)-hydroxymethyl-3,5-dimethyl-4-(methoxymethoxy)-5H-thiophen-2-one, a key intermediate in the synthesis of thiolactomycin has been carried out by a Carica papaya lipase-mediated resolution protocol to
Unexpected Direct Synthesis of N-Vinyl Amides through Vinyl Azide–Enolate [3+2] Cycloaddition
Choi, Hans,Shirley, Harry J.,Hume, Paul A.,Brimble, Margaret A.,Furkert, Daniel P.
supporting information, p. 7420 - 7424 (2017/06/13)
The unexpected synthesis of industrially important N-vinyl amides directly from aldehydes and α,β-unsaturated N-vinyl amides from esters is reported. This reaction probably proceeds through an initial [3+2] azide–enolate cycloaddition involving a vinyl azide generated in situ. A survey of the reaction scope and preliminary mechanistic findings supported by quantum computational analysis are reported, with implications for the future development of atom-efficient amide synthesis. Intriguingly, this study suggests that (cautious) reevaluation of azidoethene as a synthetic reagent may be warranted.
Synthesis, antimalarial evaluation and molecular docking studies of some thiolactone derivatives
Sainy, Jitendra,Sharma, Rajesh
, p. 350 - 359 (2017/01/10)
In present study novel thiolactone derivatives were designed, synthesized and characterized by various analytical techniques such as IR, 1H NMR, 13C NMR, mass spectral data and elemental analysis. All synthesized compounds were evaluated for in?vitro antimalarial activity against Dd2 and 3d7 strain of P.?falciparum. All synthesized compounds were also subjected for molecular docking study with pf KASI/II enzyme to analyze their binding orientation in the active site of the enzyme. Compounds 5d, 5e, and 5i found to be most potent with IC50 in the range of 0.09–0.19?μM and 0.03–0.04?μM against the Dd2 strain and 3D7 strain respectively as well as they showed good binding affinities with the residues of the active site of pf KASI/II.
