77759-08-1Relevant academic research and scientific papers
4,5,6 and 7-indole and indoline derivatitives, their preparation and use
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, (2008/06/13)
A substituted 4-, 5-, 6-, and 7-indole derivative of Formula (I) wherein A is a group having formula (IIA), (IIB), (IIC) wherein X, U, Y, R3to R12, Z, W, n and m are as defined above. The compounds are potent serotonin reuptake inhib
A new method for the synthesis of 2,6-dinitro and 2-halo-6-nitrostyrenes
Mundla
, p. 6319 - 6321 (2007/10/03)
A new method for the synthesis of 2-halo-6-nitrostyrenes from 2-halo-6-nitrotoluenes is disclosed. Also described is a one-pot process for the synthesis of 2,6-dinitristyrene from 2,6-dinitrotoluene. (C) 2000 Elsevier Science Ltd.
New photolabile protecting groups in nucleoside and nucleotide chemistry - Synthesis, cleavage mechanisms and applications
Giegrich,Eisele-Buehler,Hermann,Kvasyuk,Charubala,Pfleiderer
, p. 1987 - 1996 (2007/10/03)
New photolabile protecting groups have been found in the 2-(2- nitrophenyl)ethoxycarbonyl and the 2-(2-nitrophenyl)ethylsulfonyl group, respectively. The influence of substituents at the phenyl ring as well as the side-chain has been investigated regarding the photolysis rates on irradiation at 365 mn. β-Branching in the side-chain leads to highly increased rates of photodeprotection. A new type of photocleavage mechanism consisting of a photoinduced β-elimination process is proposed.
Nucleoside derivatives with photolabile protective groups
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, (2008/06/13)
The invention relates to nucleoside derivatives having photolabile protective groups of the general formula (I) STR1 in which R1 =H, NO2, CN, OCH3, halogen or alkyl or alkoxyalkyl having 1 to 4 C atoms R2 =H, OCH3 R3 =H, F, Cl, Br, NO2 R4 =H, halogen, OCH3, or an alkyl radical having 1 to 4 C atoms R5 =H or a usual functional group for preparing oligonucleotides R6 =H, OH, halogen or XR8, where X=O or S and R8 represents a protective group usual in nucleotide chemistry, B=adenine, cytosine, guanine, thymine, uracil, 2,6-diaminopurin-9-yl, hypoxanthin-9-yl, 5-methylcytosin-1-yl, 5-amino-4-imidazolcarboxamid-1-yl, or 5-amino-4-imidazolcarboxamid-3-yl, where in the case of B=adenine, cytosine or guanine, the primary amino function optionally exhibits a permanent protective group. These derivatives may be used for the light-controlled synthesis of oligonucleotides on a DNA chip.
Synthesis of 2'-deoxyribofuranosyl indole nucleosides related to the antibiotics SF-2140 and neosidomycin
Girgis,Cottam,Robins
, p. 361 - 373 (2007/10/02)
The 2'-deoxyribofuranose analog of the naturally occurring antibiotics SF-2140 and neosidomycin were prepared by the direct glycosylation of the sodium salts of the appropriate indole derivatives, with 1-chloro-2-deoxy-3,5-di-O-p-toluoyl-α-D-erythropentofuranose. Thus, treatment of the sodium salt of 4-methoxy-1H-indol-3-ylacetonitrile with 5 provided the blocked nucleoside, 4-methoxy-1-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythropentofuranosyl)-1 -indol-3-ylacetonitrile, which was treated with sodium methoxide to yield the SF-2140 analog, 4-methoxy-1-(2-deoxy-β-D-erythropentofuranosyl)-1H-indol-3-ylacetoni rile. The neosidomycin analog was prepared by treatment of the sodium salt of 1H-indol-3-ylacetonitrile with 5 to obtain the blocked intermediate 1-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythropentofuranosyl)-1H-3-ylacet nitrile followed by sodium methoxide treatment to give 1-(2-deoxy-β-D-erythropentofuranosyl)-1H-indol-3-ylacetonitrile and finally conversion of the nitrile function of 7b to provide 1-(2-deoxy-β-D-erythropentofuranosyl)-1H-indol-3-ylacetamide. In a similar manner, indole and several other substituted indoles including 1H-indole-4-carbonitrile, 4-nitro-1H-indole, 4-chloro-1H-indole-2-carboxamide and 4-chloro-1H-indole-2-carbonitrile were each glycosylated and deprotected to provide 1-(2-deoxy-β-D-erythropentofuranosyl)-1H-indole, 1-(2-deoxy-β-D-erythropentofuranosyl)-1H-indole-4-carbonitrile, 4-nitro-1-(2-deoxy-β-D-erythropentofuranosyl)-1H-indole, 4-chloro-1-(2-deoxy-β-D-erythropentofuranosyl)-1H-indole-2-carboxami e and 4-chloro-1-(2-deoxy-β-D-erythropentofuranosyl)-1H-indole-2-carbonitr le, respectively. The 2'-deoxyadenosine analog in the indole ring system was prepared for the first time by reduction of the nitro group of 11c using palladium on carbon thus providing 4-amino-1-(2-deoxy-β-D-erythropentofuranosyl)-1H-indole (1,3,7-trideaza-2'-deoxyadenosine).
