159846-14-7Relevant academic research and scientific papers
New Spisulosine Derivative promotes robust autophagic response to cancer cells
Chaturvedi, Priyank,Datta, Dipak,Ganesher, Asha,Meena, Sanjeev,Mitra, Kalyan,Panda, Gautam,Sahai, Rohit
, (2020/01/13)
Therapy resistance by evasion of apoptosis is one of the hallmarks of human cancer. Therefore, restoration of cell death by non-apoptotic mechanisms is critical to successfully overcome therapy resistance in cancer. By rational drug design approach, here we try to provide evidence that subtle changes in the chemical structure of spisulosine completely switched its cytotoxic function from apoptosis to autophagy. Our most potent molecule (26b) in a series of 16 synthesized derivatives showed robust autophagic cell death in diverse cancer cells sparing normal counterpart. Compound 26b mediated lethal autophagy induction was confirmed by formation of characteristic autophagic vacuoles, LC3 puncta formation, upregulation of signature autophagy markers like Beclin and Atg family proteins. Altogether, we have detected novel autophagy inducer small molecule which can be tested further for drug discovery research.
Total Synthesis of the Post-translationally Modified Polyazole Peptide Antibiotic Goadsporin
Dexter, Hannah L.,Williams, Huw E. L.,Lewis, William,Moody, Christopher J.
supporting information, p. 3069 - 3073 (2017/03/13)
The structurally unique polyazole antibiotic goadsporin contains six heteroaromatic oxazole and thiazole rings integrated into a linear array of amino acids that also contains two dehydroalanine residues. An efficient total synthesis of goadsporin is repo
CERAMIDE DERIVATIVE HAVING SMS2 INHIBITORY ACTIVITY
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Paragraph 0071, (2017/09/02)
PROBLEM TO BE SOLVED: To provide a ceramide derivative having excellent SMS2 inhibitory activity, preferably, a ceramide derivative having high SMS2 selectivity. SOLUTION: The present invention provides a compound represented by formula (I) or a pharmaceu
Studies toward the synthesis of (-)-zampanolide: Preparation of the macrocyclic core
Troast, Dawn M.,Yuan, Jiayi,Porco Jr., John A.
experimental part, p. 1701 - 1711 (2009/07/18)
Studies towards the synthesis of the macrocyclic core of (-)-zampanolide are reported. The synthetic approach features a one-pot reduction/vinylogous aldol reaction for construction of the C-15-C-20 fragment, an intramolecular silyl-modified Sakurai (ISMS) reaction for construction of the 2,6-cis-disubstituted exo-methylene pyran subunit, and use of an sp 2-sp3 Stille reaction for macrocyclization.
A practical method for selective cleavage of a tert-butoxycarbamoyl N-protective group from N,N-diprotected α-amino acid derivatives using montmorillonite K-10
Hernandez, J. Nicolas,Crisostomo, Fernando R. Pinacho,Martin, Tomas,Martin, Victor S.
, p. 5050 - 5058 (2008/03/18)
A new, practical, and mild procedure for the selective cleavage of a tert-butoxycarbonyl group (Boc) in N-Boc-N-acyl-diprotected amines is described. When applied to α-amino acids, complete integrity of the stereochemistry was observed. The use of N,N-di-Boc-α-amino-δ- and γ-hydroxy esters provided both δ- and γ-lactones in very good yields. The method is based on the use of Montmorillonite K-10 either in CH 2Cl2 at room temperature or in toluene at 65°C and is compatible with the presence of a large range of functional and other protecting groups in the substrates. In most cases virtually pure samples are obtained after filtration and removal of solvents. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
(+)-Saxitoxin: A first and second generation stereoselective synthesis
Fleming, James J.,McReynolds, Matthew D.,Du Bois
, p. 9964 - 9975 (2008/03/17)
A stereoselective synthesis of the bis-guanidinium toxin (+)-saxitoxin (STX), the agent infamously associated with red tides and paralytic shellfish poisoning, is described. Our approach to this unique natural product advances through an unusual nine-membered ring guanidine intermediate 39 en route to the tricyclic skeleton that defines STX. The effectiveness of this strategy is notable, as only four steps are needed to transform 39 into the target molecule, including a four-electron alkene oxidation catalyzed by OsCl3. Construction of the critical monocyclic guanidine has been achieved through two channels, the first of which makes use of Rh-catalyzed C-H amination and highlights a novel class of heterocyclic N,O-acetals as iminium ion equivalents for crafting functionalized amines. A second route to 39 relies on a stereoselective acetylide dianion addition to a serine-based nitrone, thereby facilitating the preparation of STX in just 14 linear steps from commercial material.
Total synthesis of the thiopeptide antibiotic amythiamicin D
Hughes, Rachael A.,Thompson, Stewart P.,Alcaraz, Lilian,Moody, Christopher J.
, p. 15644 - 15651 (2007/10/03)
The thiopeptide (or thiostrepton) antibiotics are a class of sulfur containing highly modified cyclic peptides with interesting biological properties, including reported activity against MRSA and malaria. Described herein is the total synthesis of the thi
Total synthesis of the thiopeptide amythiamicin D.
Hughes, Rachael A,Thompson, Stewart P,Alcaraz, Lilian,Moody, Christopher J
, p. 946 - 948 (2007/10/03)
The first total synthesis of the thiopeptide antibiotic amythiamicin D is described.
Facile Route to 3,5-Disubstituted Morpholines: Enantioselective Synthesis of O-Protected trans-3,5-Bis(hydroxymethyl)morpholines
Dave, Rajesh,Andre Sasaki
, p. 15 - 18 (2007/10/03)
(Equation presented) trans-3,5-Bis(benzyl/terf-butyldiphenylsilyloxymethyl) morpholines, promising candidates for the C2-symmetric class of chiral reagents, were prepared with excellent optical purity. A key step in the synthesis is the couplin
A new selective cleavage of N,N-dicarbamoyl-protected amines using lithium bromide
Hernandez, J. Nicolas,Ramirez, Miguel A.,Martin, Victor S.
, p. 743 - 746 (2007/10/03)
A mild and new procedure for the selective cleavage of an alkoxycarbonyl group (Boc, CBz) in N,N-dicarbamoyl-protected amino compounds is described. The method is based on the use of lithium bromide in acetonitrile and is compatible with a large range of other functionalities present in the substrates. Compared with other reported methodologies, the procedure is particularly useful for the Cbz-selective cleavage in N,N-Ts,Cbz-diprotected amines. A rationalization of the selectivity supported by ab initio calculations is also presented.
