146924-95-0Relevant academic research and scientific papers
Stereoselective synthesis of-lactams under diverse conditions: Unprecedented Observations
Das, Aparna,Bose, Ajay K.,Banik, Bimal Krishna
, p. 917 - 925 (2020/12/04)
ferent reaction conditions have been used for this study. It is important to note that the stereochemistry of the-lactam formation reaction depends on the conditions of the experiments, structures of the imines and acid chlorides, order of addition of the
Microwave-induced cycloaddition of imines with acid chlorides in absence of a tertiary amine: Unprecedented synthesis of β-lactams in dimethylformamide
Yadav, Ram Naresh,Chavez, Ashlee,Banik, Bimal Krishna
, p. 1365 - 1367 (2020/06/27)
Synthesis β-lactams in N,N-dimethylformamide proceeds through cycloaddition of acid chlorides with imines in a domestic microwave oven in the absence of a tertiary base. This is an unprecedented observation.
Synthesis and biological evaluation of novel larotaxel analogues
Ren, Sumei,Wang, Yujie,Wang, Junfei,Gao, Dingding,Zhang, Minmin,Ding, Ning,Li, Yingxia
supporting information, p. 692 - 710 (2018/07/29)
Taxoids are a class of successful drugs and have been successfully used in chemotherapy for a variety of cancer types. However, despite the hope and promises that these taxoids have engendered, their utility is hampered by some clinic limitations. Extensive structure-activity relationship (SAR) studies of toxoids have been performed in many different laboratories. Whereas, SAR studies that based on the new-generation toxoid, larotaxel, have not been reported yet. In view of the advantages in preclinical and clinical data of larotaxel over former toxoids, new taxoids that strategicly modified at the C3’/C3′-N and C2 positions of larotaxel were designed, semi-synthesized, and examined for their potency and efficacy in vitro. As a result, it has been shown that the majority of these larotaxel analogues are exceptionally potent against both drug-sensitive tumor cells and tumor cells with drug resistance arising from P-glycoprotein over expression. Further in vivo antitumor efficacies investigations revealed A2 might be a potent antitumor drug candidate for further preclinical evaluation.
Paclitaxel Biosynthesis: Adenylation and Thiolation Domains of an NRPS TycA PheAT Module Produce Various Arylisoserine CoA Thioesters
Muchiri, Ruth,Walker, Kevin D.
, p. 1415 - 1425 (2017/03/23)
Structure-activity relationship studies show that the phenylisoserinyl moiety of paclitaxel (Taxol) is largely necessary for the effective anticancer activity. Several paclitaxel analogues with a variant isoserinyl side chain have improved pharmaceutical
A mild and selective reduction of β-lactams: Rh-catalyzed hydrosilylation towards important pharmacological building blocks
Bornschein, Christoph,Lennox, Alastair J. J.,Werkmeister, Svenja,Junge, Kathrin,Beller, Matthias
, p. 1915 - 1919 (2015/03/18)
Four-membered N-heterocyclic compounds exhibit a broad range of pharmacological activities. Herein, we report a useful rhodium-catalyzed protocol for the activation of phenylsilane to reduce tertiary β-lactams. Reaction with the tertiary amides was select
Stereospecific novel glycosylation of hydroxy β-lactams via iodine-catalyzed reaction: A new method for optical resolution
Banik, Bimal K.,Manhas, Maghar S.
, p. 10769 - 10779 (2013/01/15)
Glycosylation of racemic and optically active α-hydroxy β-lactams by reaction with a few glycal derivatives in the presence of catalytic amounts of iodine has provided stereospecific formation of α-glycosides. This method has been extended for the prepara
A new enzymatic strategy for the preparation of (2R,3S)-3-phenylisoserine: a key intermediate for the Taxol side chain
Forro, Eniko,Fueloep, Ferenc
scheme or table, p. 637 - 639 (2010/08/03)
Burkholderia cepacia lipase PS-IM catalysed the hydrolysis of racemic ethyl 3-amino-3-phenyl-2-hydroxypropionate with excellent enantioselectivity (E >200), when the reaction was performed with added H2O as a nucleophile, in iPr2O, at 50 °C. The hydrolysis of the less reactive enantiomeric ethyl 3-amino-3-phenyl-2-hydroxypropionate with 18% HCl afforded the corresponding enantiomerically pure (2R,3S)-3-amino-3-phenyl-2-hydroxypropionic acid hydrochloride, a key intermediate for the Taxol side chain.
A facile iodine-catalyzed glycosylation: Enantiomerically pure β-lactams with the thienamycin side chain
Banik, Bimal K.,Zegrocka, Oliwia,Manhas, Maghar S.,Bose, Ajay K.
scheme or table, p. 2443 - 2454 (2010/04/27)
A facile iodine-catalyzed glycosylation of the hydroxyethyl side chain as present in thienamycin side chain has been achieved with tri-O-acetyl-D-glucal. This method has produced two separable diasteromeric α-glycosides in excellent yields which on acid-i
Arthrobacter sp.: a lipase of choice for the kinetic resolution of racemic arylazetidinone precursors of taxanoid side chains
Anand, Naveen,Kapoor, Munish,Ahmad, Khursheed,Koul, Surrinder,Parshad, Rajinder,Manhas, Kuldip S.,Sharma, Rattan L.,Qazi, Ghulam N.,Taneja, Subhash C.
, p. 1059 - 1069 (2008/01/07)
The native strain of Arthrobacter sp. (MTCC 5125) bearing a lipase has been found to be the most effective in the kinetic resolution of racemic arylazetidinones for producing cis-(3R,4S)-3-acetoxy-1-(4-methoxyphenyl)-4-phenyl-2-azetidinone, cis-(3R,4S)-3-
N-Thiolated β-lactam antibacterials: Effects of the N-organothio substituent on anti-MRSA activity
Heldreth, Bart,Long, Timothy E.,Jang, Seyoung,Reddy, G. Suresh Kumar,Turos, Edward,Dickey, Sonja,Lim, Daniel V.
, p. 3775 - 3784 (2007/10/03)
A study on the structure-activity profiles of N-thiolated β-lactams 1 is reported which demonstrates the importance of the N-organothio moiety on antibacterial activity. Our results indicate that elongation of the N-alkylthio residue beyond two carbons, or extensive branching within the organothio substituent, diminishes antibacterial effects. Of the derivatives we examined, the N-sec-butylthio β-lactam derivative 5g possesses the strongest growth inhibitory activity against methicillin-resistant Staphylococcus aureus strains. Sulfur oxidation state is important, as the N-sulfenyl and N-sulfinyl groups provide for the best antibacterial activity, while lactams bearing the N-sulfonyl or N-sulfonic acid functionalities have much weaker or no anti-MRSA properties. Stereochemistry within the organothio chain does not seem to be a significant factor, although for N-sec-butylthio β-lactams 15a-d, the 3R,4S-lactams 15c, d are more active than the 3S,4R-stereoisomers 15a, b in agar diffusion experiments. The N-methylthio lactams are the most sensitive to the presence of glutathione, followed by N-ethylthio and N-sec-butylthio lactams, which indicates that bioactivity and perhaps bacterial selectivity of the lactams may be related to the amount of organothiols in the bacterial cell. These results support the empirical model for the mechanism of action of the compounds in which the lactam transverses the bacterial membrane to deliver the organothio moiety to its cellular target.
