15937-07-2Relevant articles and documents
Regiospecific dihydroindoles directly from β-arylethylamines by photoinduced SET reaction: One pot 'wavelength switch' approach to benzopyrrolizidines related to mitomycin
Pandey,Sridhar,Bhalerao
, p. 5373 - 5376 (1990)
Regiospecific highly substituted indole derivatives are synthesised by photoinduced SET initiated cyclisation of β-arylethylamines and development of sequential one pot approach to benzopyrrolizidines related to mitomycin at two different wavelengths under SET conditions is reported.
Aerobic Dehydrogenation of N-Heterocycles with Grubbs Catalyst: Its Application to Assisted-Tandem Catalysis to Construct N-Containing Fused Heteroarenes
Kawauchi, Daichi,Noda, Kenta,Komatsu, Yoshiyuki,Yoshida, Kei,Ueda, Hirofumi,Tokuyama, Hidetoshi
supporting information, p. 15793 - 15798 (2020/10/12)
An aerobic dehydrogenation of nitrogen-containing heterocycles catalyzed by Grubbs catalyst is developed. The reaction is applicable to various nitrogen-containing heterocycles. The exceptionally high functional group compatibility of this method was confirmed by the oxidation of an unprotected dihydroindolactam V to indolactam V. Furthermore, by taking advantage of the oxygen-mediated structural change of the Grubbs catalyst, we integrated ring-closing metathesis and subsequent aerobic dehydrogenation to develop the novel assisted-tandem catalysis using molecular oxygen as a chemical trigger. The utility of the assisted-tandem catalysis was demonstrated by the concise synthesis of N-containing fused heteroarenes including a natural antibiotic, pyocyanine.
Compound for hair dyeing and single dosage type hair dye containing compound
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Paragraph 0049; 0051; 0052; 0053; 0054, (2018/09/21)
The invention relates to a compound for hair dyeing and single dosage type hair dye containing the compound. The compound has a structure formula shown as a formula I or a formula II shown in description, wherein X in the formula II is Br or Cl. The raw material compound provided by the invention has the beneficial effects that 1, new raw materials can easily permeate into hair and are subjected to auto-oxidation polymerization in air inside the hair; melanin generating natural black achieves a dyeing effect; the advantages of fast coloring and coloring durability are realized; the generated melanin is a polymer; the melanin pre se is a substance generated by human body melanin cells and cannot reversely enter the human body in the hair; 2, the new raw materials and the hair dye provided by the invention have a good dyeing effect; particularly universality is realized; human hair with various colors such as white color, grey white color, faint yellow color, golden yellow color and redcolor can be dyed into natural black.
NOVEL PYRAZOLE AND IMIDAZOLE DERIVATIVES USEFUL AS OREXIN ANTAGONISTS
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Page/Page column 44, (2012/09/10)
The present invention relates to pyrazole and imidazole derivatives of formula (I) wherein U, V, L, X, Y, R1, (R2)n and (R3)m and ring A are as described in the description, to their preparation, to pharmaceutically acceptable salts thereof, and to their use as pharmaceuticals, to pharmaceutical compositions containing one or more compounds of formula (I), and especially to their use as orexin receptor antagonists.
Effect of structural modification in the amine portion of substituted aminobutyl-benzamides as ligands for binding σ1 and σ2 receptors
Fan, Kuo-Hsien,Lever, John R.,Lever, Susan Z.
experimental part, p. 1852 - 1859 (2011/05/02)
5-Bromo-N-[4-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-butyl)]-2, 3-dimethoxy-benzamide (1) is one of the most potent and selective σ2 receptor ligands reported to date. A series of new analogs, where the amine ring fused to the aromatic ring was varied in size (5-7) and the location of the nitrogen in this ring was modified, has been synthesized and assessed for their σ1/σ2 binding affinity and selectivity. The binding affinity of an open-chained variant of 1 was also evaluated. Only the five-membered ring congener of 1 displayed a higher σ1/σ2 selectivity, derived from a higher σ2 affinity and a lower σ1 affinity. Positioning the nitrogen adjacent to the aromatic ring in the five-membered and six-membered ring congeners dramatically decreased affinity for both subtypes. Thus, location of the nitrogen within a constrained ring is confirmed to be key to the exceptional σ2 receptor binding affinity and selectivity for this active series.
Synthesis and biological evaluation of nonclassical 2,4-diamino-5- methylpyrido[2,3-d]pyrimidines with novel side chain substituents as potential inhibitors of dihydrofolate reductases
Gangjee, Aleem,Vasudevan, Anil,Queener, Sherry F.
, p. 479 - 485 (2007/10/03)
Nine novel 2,4-diamino-5-methyl-6-substituted-pyrido[2,3-d]pyrimidines, 2-10, were synthesized as potential inhibitors of Pneumocystis carinii dihydrofolate reductase (pcDHFR) and Toxoplasma gondii dihydrofolate reductase (tgDHFR). Compounds 2-5 were designed as conformationally restricted analogues of trimetrexate (TMQ), in which rotation around τ3 was constrained by incorporation of the side chain nitrogen as part of an indoline or an indole ring. Analogue 6, which has an extra atom between the side chain nitrogen and the phenyl ring, has its nitrogen as part of a tetrahydroisoquinoline ring. Analogues 7-9 are epiroprim (Ro 11-8958) analogues and contain a pyrrole ring as part of the side chain substitution on the phenyl ring similar to epiroprim. These analogues were designed to investigate the role of the pyrrole substitution on the phenyl ring of 2,4- diamino-5-methyl-6-(anilinomethyl)pyrido[2,3-d]pyrimidines. Molecular modeling indicated that a pyrrole substituent in the ortho position of the side chain phenyl ring was most likely to interact with pcDHFR in a manner similar to the pyrrole moiety of epiroprim. Analogue 10, in which a phenyl ring replaced a methoxy group, was synthesized to determine the contribution of a phenyl ring on selectivity, lipophilicity, and cell penetration. The synthesis of analogues 2-4 was achieved via reductive amination of 2,4- diamino-5-methyl 6-carboxaldehyde with the appropriately substituted indolines. The indolines were obtained from the corresponding indoles via NaCNBH3 reductions. Analogues 5-10 were synthesized by nucleophilic displacement of 2,4-diamino-5-methyl-6-(bromemethyl)-pyrido[2,3-d]pyrimidine with the 5-methoxyindolyl anion, 6,7-dimethoxytetrahydroisoquinoline, the appropriately substituted pyrroloaniline or 2-methoxy-5-phenylaniline. The pyrroloanilines were synthesized in two steps by treating the substituted nitroanilines with 2,5-dimethoxy-tetrahydrofuran to afford the nitropyrrole intermediates, followed by reduction of the nitro group with Raney Ni. The analogues were more potent than trimethoprim and epiroprim and more selective than TMQ and piritrexim against pcDHFR and tgDHFR. Compounds 5 and 10 had IC50 values of 1 and 0.64 μM, respectively, for the inhibition of the growth of T. gondii cells in culture, and showed excellent culture IC50/enzyme IC50 ratios, which were correlated with their calculated log P values, indicating a direct relationship between calculated lipephilicity and cell penetration.
Generation of the Neurotoxin 6-Hydroxydopamine by Peroxidase/H2O2 Oxidation of Dopamine
Napolitano, Alessandra,Crescenzi, Orlando,Pezzella, Alessandro,Prota, Giuseppe
, p. 917 - 922 (2007/10/02)
At physiological pH values, oxidation of the neurotransmitter dopamine(DA) by the peroxidase/H2O2 system leads to, besides dopaminochrome and 5,6-dihydroxyindole resulting from oxidative cyclization of dopaminequinone (DQ), significant amounts of the neurotoxin 6-hydroxydopamine (6-OHDA) in the oxidized quinonoid form (topaminequinone, TQ).Formation of TQ was shown to depend critically on the presence of hydrogen peroxide in the reaction medium and was not observed when DA oxidation was carried out using the tyrosinase/O2 system or chemical agents such as periodate or ferricyanide.These and other data suggest that, under the conditions adopted, nucleophilic attack of the hydrogen peroxide anion on DQ leading to TQ significantly competes with the intramolecular cyclization path.In line with this mechanism, the reaction course was not affected by the presence of hydroxyl radical scavengers.Peroxidase/H2O2 oxidation of the model N-acetyldopamine (1) gave, as expected, the 2-hydroxy-1,4-benzoquinone 3 in yields up to 55percent, depending on the catecholamine/H2O2 mole ratio.Likewise, reaction of 4-methyl-1,2-benzoquinone (4) with hydrogen peroxide afforded 2-hydroxy-5-methyl-1,4-benzoquinone (5) in good yields.Collectively, these results would point to the possibility that intraneuronal formation of 6-OHDA is associated with an increased production of hydrogen peroxide under oxidative stress conditions.
