81609-20-3Relevant academic research and scientific papers
C-3 alkylation of oxindole with alcohols by Pt/CeO2 catalyst in additive-free conditions
Chaudhari, Chandan,Siddiki, S. M. A. Hakim,Kon, Kenichi,Tomita, Atsuko,Tai, Yutaka,Shimizu, Ken-Ichi
, p. 1064 - 1069 (2014/04/03)
In a series of transition metal-loaded CeO2 catalysts and Pt-loaded catalysts on various supports, Pt-loaded CeO2 shows the highest activity for the selective C-3 alkylation of oxindole with octanol. The catalyst is effective for alkylation of oxindole and N-substituted oxindole with a series of substituted benzyl, linear, hetero-aryl alcohols under additive-free conditions and is recyclable. Our results demonstrate the first additive-free catalytic system for this reaction. Mechanistic studies show that this system is driven by the borrowing-hydrogen pathway. Structure-activity relationship studies show that co-presence of surface Pt0 species on Pt metal clusters and basic support is indispensable for this catalytic system. This journal is the Partner Organisations 2014.
Identification of indoline-2-thione analogs as novel potent inhibitors of α-melanocyte stimulating hormone induced melanogenesis
Thanigaimalai, Pillaiyar,Lee, Ki-Cheul,Sharma, Vinay Kumar,Sharma, Niti,Roh, Eunmiri,Kim, Youngsoo,Jung, Sang-Hun
, p. 1285 - 1288 (2011/11/12)
Based on the hits, 3,4-dihydroquinazoline-2-thione (1) and benzimidazole-2-thione (2), a series of indole-2-thione (3) and indole-2-thiol inhibitors (4) of melanogenesis were designed, synthesized and evaluated in melanoma B16 cells under the stimulant of α-melanocyte stimulating hormone (α-MSH). The indole-2-thione compounds (3a-g) exhibited an effective inhibitory activity on melanin synthesis. The Structure-Activity Relationship (SAR) studies of 2 have revealed that in potent inhibitor 3a (>100% inhibition at 30μM, IC50=1.40μM) the role of nitrogen (3-N) at 3-position is insignificance. In addition, the hydrophobic substituents of 3 were better than the hydrophilic one. However, conversion of thione (-C=S, 3) to thiol (-C-SH, 4) led to decrease in the potency.
REGIOSELECTIVE C-3 ALKYLATIONS OF OXINDOLE DIANION
Kende, Andrew, S.,Hodges, John C.
, p. 1 - 10 (2007/10/02)
Oxindole is converted to its dianion by treatment with two equivalents each of n-BuLi and TMEDA.Alkylations with a number of common electrophiles define the scope of synthetically useful tramsformations leading to 3-monosubstituted and 3,3-disubstituted o
