103549-24-2Relevant articles and documents
Biomimetic semi-synthesis of fradcarbazole A and its analogues
Wang, Liping,Mei, Xiangui,Wang, Cong,Zhu, Weiming
, p. 7990 - 7997 (2015)
The first synthesis of fradcarbazole A (1) has been accomplished by using a biomimetic intramolecular cyclization/dehydration to construct the staurosporine-thiazole-indole skeleton. The phenyl and oxazole analogues of fradcarbazole A (2-4) were also synthesized using the same strategy. Compounds 1-4 displayed cytotoxicity against A549 cell line with IC50 values of 0.4-3.6 μM, induction of G0/G1 arrest of A549 cell cycle at 10 μM, and inhibition of PKC-β kinase with IC50 values of 0.5-0.9 μM.
A highly chemoselective Boc protection of amines using sulfonic-acid-functionalized silica as an efficient heterogeneous recyclable catalyst
Das, Biswanath,Venkateswarlu, Katta,Krishnaiah, Maddeboina,Holla, Harish
, p. 7551 - 7556 (2006)
A facile and versatile method for the chemoselective Boc protection of amines has been developed by a treatment with (Boc)2O in the presence of sulfonic-acid-functionalized silica as a catalyst. The method is general for the preparation of N-Boc derivatives of aliphatic (acyclic and cyclic), aromatic, and heteroaromatic amines; primary and secondary amines; aminols, amino-esters; and sulfonamides. The catalyst works under heterogeneous conditions and can be recycled.
Synthesis of novel oxazolyl-indoles
Roy, Sudipta,Haque, Sakhina,Gribble, Gordon W.
, p. 3948 - 3954 (2006)
We describe the synthesis of oxazolyl-indoles that are structurally related to pimprinaphine. The effect of the indole N-cyanoalkyl substituents on the 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) mediated oxidation was evaluated. Georg Thieme Verlag Stuttgart.
An efficient and highly chemoselective N-Boc protection of amines, amino acids, and peptides under heterogeneous conditions
Jahani, Fatemeh,Tajbakhsh, Mahmood,Khaksar, Samad,Azizi, Mohamad Reza
, p. 1035 - 1043 (2011)
A simple and efficient procedure for chemoselective mono-N-Boc protection of various structurally diverse amines, amino acids, and peptides with di-tert-butyl dicarbonate using Amberlyst-15 as catalyst in ethanol is described. The catalyst can be readily separated from the reaction products with simple filtration and recovered for direct reuse. No competitive side-reactions such as formation of isocyanate, urea, oxazolidinone, and N,N-di-Boc derivatives were observed.
A generic approach for the catalytic reduction of nitriles
Caddick, Stephen,Judd, Duncan B.,Lewis, Alexandra K. De K.,Reich, Melanie T.,Williams, Meredith R. V.
, p. 5417 - 5423 (2003)
The scope of nickel boride mediated reduction of nitriles has been extended further to allow the preparation of Boc protected amines via a mild catalytic process. It is noteworthy that the toxicity of this procedure is greatly reduced due to its catalytic
Synthesis of novel tryptamine-based macrocycles using an Ugi 4-CR/microwave assisted click-cycloaddition reaction protocol
Chavez-Acevedo, Lizbeth,Miranda, Luis D.
, p. 4408 - 4412 (2015)
A practical synthesis of novel tryptamine-based macrocycles using an Ugi 4-CR/click-cycloaddition sequential reaction protocol is described. The main features of the macrocyclic scaffolds are a peptoid moiety, a 1,3-substituted indole nucleus, and a triazole ring.
Ability of the Putative Decomposition Products of 2,3-dioxetanes of Indoles to Photosensitize Cyclobutane Pyrimidine Dimer (CPD) Formation and its Implications for the “Dark” (Chemisensitized) Pathway to CPDs in Melanocytes?
Wang, Yanjing,Cacchillo, Elena M.,Niedzwiedzki, Dariusz M.,Taylor, John-Stephen
, p. 442 - 454 (2021/10/14)
The formation of cyclobutane pyrimidine dimers (CPDs) by a “dark” pathway in melanocytes has been attributed to chemisensitization by dioxetanes produced from peroxynitrite oxidation of melanin or melanin precursors. These dioxetanes are proposed to decompose to triplet state compounds which sensitize CPD formation by triplet–triplet energy transfer. To determine whether such compounds are capable of sensitizing CPD formation, the putative decomposition products of 2,3-dioxetanes of variously substituted indoles were synthesized and their triplet state energies determined at 77?K. Their ability to photosensitize CPD formation was determined by an enzyme-coupled gel electrophoresis assay in comparison with norfloxacin (NFX) which has the lowest triplet energy known to sensitize CPD formation. The decomposition products of 2,3-dioxetanes of 5-hydroxy and 5,6-dimethoxy indoles used as models for melanin precursors had lower triplet energies and were incapable of photosensitizing CPD formation. Theoretical calculations suggest that the decomposition products of the 2,3-dioxetanes of melanin precursors DHI and DHICA will have similarly low triplet energies. Decomposition products of the 2,3-dioxetanes of indoles lacking oxygen substituents had higher triplet energies than NFX and were capable of photosensitizing CPD formation, suggesting that peroxynitrite oxidation of tryptophan could play a hitherto unrecognized role in the dark pathway to CPDs.
Catalytic and Enantioselective Control of the C–N Stereogenic Axis via the Pictet–Spengler Reaction
Kim, Ahreum,Kim, Aram,Park, Sunjung,Kim, Sangji,Jo, Hongil,Ok, Kang Min,Lee, Sang Kook,Song, Jayoung,Kwon, Yongseok
supporting information, p. 12279 - 12283 (2021/05/03)
An unprecedented example of a chiral phosphoric acid-catalyzed atroposelective Pictet–Spengler reaction of N-arylindoles is reported. Highly enantioenriched N-aryl-tetrahydro-β-carbolines with C?N bond axial chirality are obtained via dynamic kinetic reso
Design and synthesis of β-carboline and combretastatin derivatives as anti-neutrophilic inflammatory agents
Kumar, Sunil,Wang, Yi-Hsuan,Chen, Po-Jen,Chang, Yu-Chia,Kashyap, Hemant K.,Shen, Ya-Ching,Yu, Huang-Ping,Hwang, Tsong-Long
, (2021/04/09)
A series of β-carboline derivatives was synthesized by the Pictet-Spengler reaction with or without the combretastatin skeleton. The structures of these derivatives were elucidated by spectroscopic techniques. All synthesized compounds were evaluated for
