38693-09-3Relevant academic research and scientific papers
4-(Indol-3-yl)thiazole-2-amines and 4-ιndol-3-yl)thiazole acylamines as novel antimicrobial agents: Synthesis, in silico and in vitro evaluation
Geronikaki, Athina,Glamo?lija, Jasmina,Ivanov, Marija,Kartsev, Victor,Kostic, Marina,Nicolaou, Ioannis,Petrou, Anthi,Simakov, Sergei,Sokovi?, Marina,Talea, Despoina,Vizirianakis, Ioannis S.
, (2021/11/08)
This manuscript deals with the synthesis and computational and experimental evaluation of the antimicrobial activity of twenty-nine 4-(indol-3-yl)thiazole-2-amines and 4-ιndol-3-yl)thiazole acylamines. An evaluation of antibacterial activity against Gram (+) and Gram (?) bacteria revealed that the MIC of indole derivatives is in the range of 0.06–1.88 mg/mL, while among fourteen methylindole derivatives, only six were active, with an MIC in the range of of 0.47–1.88 mg/mL. S. aureus appeared to be the most resistant strain, while S. Typhimurium was the most sensitive. Compound 5x was the most promising, with an MIC in the range of 0.06–0.12 mg/mL, followed by 5d and 5m. An evaluation of these three compounds against resistant strains, namely MRSA P. aeruginosa and E. coli, revealed that they were more potent against MRSA than ampicillin. Furthermore, compounds 5m and 5x were superior inhibitors of biofilm formation, compared to ampicillin and streptomycin, in terms Compounds 5d, 5m, and 5x interact with streptomycin in additive manner. The antifungal activity of some compounds exceeded or was equipotent to those of the reference antifungal agents bifonazole and ketoconazole. The most potent antifungal agent was found to be compound 5g. Drug likeness scores of compounds was in a range of ?0.63 to 0.29, which is moderate to good. According to docking studies, E. coli MurB inhibition is probably responsible for the antibacterial activity of compounds, whereas CYP51 inhibition was implicated in antifungal activity. Compounds appeared to be non-toxic, according to the cytotoxicity assessment in MRC-5 cells.
Collective Synthesis of 3-Acylindoles, Indole-3-carboxylic Esters, Indole-3-sulfinic Acids, and 3-(Methylsulfonyl)indoles from Free (N-H) Indoles via Common N-Indolyl Triethylborate
Zhang, Zhi-Wei,Xue, Hong,Li, Hailing,Kang, Huaiping,Feng, Juan,Lin, Aijun,Liu, Shouxin
supporting information, p. 3918 - 3921 (2016/08/16)
A general and direct C3 functionalization of free (N-H) indoles with readily available electrophiles such as acid chlorides, chloroformates, thionyl chloride, and methylsulfonyl chloride via a common N-indolyl triethylborate intermediate is reported. The reaction proceeds smoothly under mild conditions in up to 93% yield. Indoles with substituents at the C2, C4, C5, C6, and C7 positions are well tolerated. The easy accessibility of a variety of important 3-acylindoles, indole-3-carboxylic esters, indole-3-sulfinic acids, and 3-(methylsulfonyl)indoles demonstrates the high degree of compatibility and practicability of this method.
Synthesis, modelling and biological characterization of 3-substituted-1H-indoles as ligands of GluN2B-containing N-methyl-d-aspartate receptors
Gitto, Rosaria,De Luca, Laura,Ferro, Stefania,Russo, Emilio,De Sarro, Giovambattista,Chisari, Mariangela,Ciranna, Lucia,Alvarez-Builla, Julio,Alajarin, Ramon,Buemi, Maria Rosa,Chimirri, Alba
, p. 1040 - 1048 (2014/02/14)
A three-step synthetic pathway has been employed to synthesize a small library of 2-(4-arylpiperidin-1-yl)-1-(1H-indol-3-yl)ethanone and 2-(4-arylpiperidin-1-yl)-1-(1H-indol-3-yl)ethane-1,2-dione derivatives that have been screened in [3H]ifenp
Synthesis and biological characterization of 3-substituted-1h-indoles as ligands of GluN2B-containing N-methyl-D-aspartate receptors
Gitto, Rosaria,De Luca, Laura,Ferro, Stefania,Buemi, Maria Rosa,Russo, Emilio,De Sarro, Giovambattista,Costa, Lara,Ciranna, Lucia,Prezzavento, Orazio,Arena, Emanuela,Ronsisvalle, Simone,Bruno, Giuseppe,Chimirri, Alba
supporting information; experimental part, p. 8702 - 8706 (2012/02/16)
As an extension of our studies, novel indole derivatives were rationally designed and synthesized as ligands targeted to GluN2B/NMDA receptors. The 2-(4-benzylpiperidin-1-yl)-1-(6-hydroxy-1H-indol-3-yl)ethanone (4i) and 1-(4-benzylpiperidin-1-yl)-2-(6-hydroxy-1H-indol-3-yl)ethane-1,2-dione (6i) showed high binding affinity in [3H]ifenprodil displacement assay. By computational studies, we suggested the hypothetical interactions playing a significant role during the binding process. However, in functional and in vivo studies the most potent compound 4i did not show any activity whereas it displayed relevant affinity toward the σ2 receptor.
Quinolizidines. XXVIII. Racemic and Chiral Syntheses of Ochromianine, an Indoloquinolizidine Alkaloid from Neisosperma miana
Tozo, Fujii,Ohba, Masashi,Tachinami, Takeshi,Ohashi, Takako
, p. 75 - 78 (2007/10/02)
A full account is given of the first racemic and chiral syntheses of 11-methoxydihydrocorynantheol , a candidate structure for the Neisosperma alkaloid ochromianine.Coupling of (+/-)-trans-6-ethoxy-3-ethyl-2,3,4,5-tetrahydro-4-pyridineacetic acid ethyl ester with 2-chloro-1-(6-methoxy-1H-indol-3-yl)ethanone (4) in the presence of KBr produced the lactam ketone (+/-)-7, which was then converted into the lactam (+/-)-9 through the oxazolium salt (+/-)-8.Bischler-Napieralski cyclization of (+/-)-9 followed by catalytic hydrogenation gave the tetracyclic ester (+/-)-11.On reduction with LiAlH4, (+/-)-11 yielded the racemic target (+/-)-1.A parallel synthetic route starting from (+)-6 and 4 afforded the chiral target (-)-1 via (+)-7,8,(+)-9, and (-)-11.Identity of synthetic (-)-1 with ochromianine unequivocally established the struture and absolute stereochemistry of this alkaloid.
