6953-35-1Relevant academic research and scientific papers
A simple synthesis of 5-amino-3-(2-dimethylaminoethyl)indole [5-amino-N,N-dimethyltryptamine]
Macor,Post,Ryan
, p. 65 - 72 (1993)
A short (three step) synthesis of 5-amino-3-(2-dimethylaminoethyl)indole [5-amino-N,N-dimethyltryptamine, 4] from commercially available starting materials is presented. Reaction of 5-nitroindole with oxalyl chloride followed by dimethylamine afforded N,N-dimethyl 5-nitroindole-3-glyoxamide (1), which was reduced by diborane to 5-nitro-3-(2-dimethylaminoethyl)indole (3). Catalytic reduction of (3) afforded the title compound in 19% overall yield from 5-nitroindole.
Rationally designed tri-armed imidazole–indole hybrids as naked eye receptors for fluoride ion sensing
Jain, Anshu,Gupta, Ragini,Agarwal, Madhu
supporting information, p. 1307 - 1318 (2017/07/12)
The present communication describes the design, synthesis, and characterization of unique tri-armed imidazole–indole hybrids RA-RE for naked eye detection of fluoride ion in 9:1 DMSO–water at concentration level of 1.5 ppm, which is recommended permissible limit of fluoride ion. Molecular structures of the receptors are so fabricated that both heterocyclic units, namely, indole and imidazole have been rationally used as chromophore and binding unit, respectively. Strategical introduction of nitro group(s) at the fifth position of indole ring remarkably enhances the binding ability of receptor RD making it highly selective toward fluoride ion (tetrabutylammonium salt) over other typical anionic species. The sensing event can be visualized by naked eyes swiftly with color change. This observation is well corroborated by a redshift of 80 nm in UV–visible spectroscopic studies. A peak at 16.1 ppm due to HF2- in 1H NMR titration validates the deprotonation of imidazolium N?H by fluoride ion.
Facile synthesis of biologically important indole based quinoxalines
Kamila, Sukanta,Ankati, Haribabu,Biehl, Edward R.
experimental part, p. 94 - 104 (2011/09/12)
Condensation of 1,2-phenylenediamine with a variety of indole based aldehydes, prepared from the corresponding acid chloride in presence of HSnBu3, furnishes (1H-indol-3-yl)quinoxalines. In addition, 1,2-phenylenediamines substituted with a strong electron-withdrawing group at the para position, provides 6-substituted (1H-indol-3-yl)quinoxalines. Several biologically important quinoxalines were prepared in the same way. The yields are good to excellent in all cases. However, 1,2-phenylenediamine substituted with the weakly electron-donating methyl group, gives an inseparable mixture of 6-methyl and 7-methyl isomers of (1H-indol-3-yl)quinoxaline. All the compounds were characterized by 1H NMR, 13C NMR and IR spectroscopy. ARKAT USA, Inc.
Total synthesis and bioactivity of the marine alkaloid pityriacitrin and some of its derivatives
Zhang, Puyong,Sun, Xiaofei,Xu, Bin,Bijian, Krikor,Wan, Shengbiao,Li, Guigen,Alaoui-Jamali, Moulay,Jiang, Tao
scheme or table, p. 6089 - 6097 (2012/01/03)
We report herein the chemical synthesis and biological evaluation of β-carboline alkaloid pityriacitrin and some of its new derivatives. Using tryptophan or 5-hydroxytryptophan and 5-substituted indole-3-glyoxals as the starting materials, pityriacitrin and some of its derivatives were synthesized via the acid-catalyzed Pictet-Spengler reaction and fully characterized by 1H and 13C NMR, mass spectroscopy and IR determinations. Biological studies revealed that pityriacitrin has a weak antiproliferative activity against a panel of breast and prostate cancer cell lines, whereas some of its derivatives exhibited stronger and potent activity, which was associated with induction of both cell apoptosis and necrosis.
Synthesis of 4-, 5-, 6-, and 7-azidotryptamines
Friedrich, Anne,Br?se, Stefan,O'Connor, Sarah E.
supporting information; body text, p. 75 - 76 (2009/04/14)
Synthesis of azidotryptamines from commercially available nitroindoles via the corresponding amino tryptamines in good overall yields (15-38%) is presented.
Identification of anxiolytic/nonsedative agents among indol-3- ylglyoxylamides acting as functionally selective agonists at the γ-aminobutyric acid-A (GABAA) α2 benzodiazepine receptor
Taliani, Sabrina,Cosimelli, Barbara,Da Settimo, Federico,Marini, Anna Maria,La Motta, Concettina,Simorini, Francesca,Salerno, Silvia,Novellino, Ettore,Greco, Giovanni,Cosconati, Sandro,Marinelli, Luciana,Salvetti, Francesca,L'Abbate, Gianluca,Trasciatti, Silvia,Montali, Marina,Costa, Barbara,Martini, Claudia
scheme or table, p. 3723 - 3734 (2010/04/05)
Anxioselective agents may be identified among compounds binding selectively to the α2βxγ2 subtype of the γ-aminobutyric acid-A (GABAA)/central benzodiazepine receptor (BzR) complex and behaving as agonists or among compounds binding with comparable potency to various BzR subtypes but eliciting agonism only at the α2βxγ2 receptor. Because of subtle steric differences among BzR subtypes, the latter approach has proved much more successful. A biological screening within the class of indol-3-ylglyoxylamides 1-3 allowed us to identify compounds 1c and 2b as potential anxiolytic/nonsedative agents showing α2 selective efficacy in vitro and anxioselective effects in vivo. According to molecular modeling studies, and consistently with SARs accumulated in the past decade, 5-NO2- and 5-H-indole derivatives would preferentially bind to BzR by placing the indole ring in the LDi and the L2 receptor binding sites, respectively.
Novel and potent oxazolidinone antibacterials featuring 3-indolylglyoxamide substituents
Takhi, Mohamed,Singh, Gurpreet,Murugan,Thaplyyal, Nirvesh,Maitra, Soma,Bhaskarreddy,Amarnath,Mallik, Arundhuti,Harisudan,Trivedi, Ravi Kumar,Sreenivas,Selvakumar,Iqbal, Javed
scheme or table, p. 5150 - 5155 (2009/05/26)
Novel oxazolidinone antibacterials bearing a variety of 3-indolylglyoxamide substituents have been explored in an effort to improve the spectrum and potency of this class of agents. A subclass of this series was also made with the diversity at C-5 terminus. These derivatives have been screened against a panel of clinically relevant Gram-positive pathogens and fastidious Gram-negative organisms. Several analogs in this series were identified with in vitro activity superior to linezolid (MIC = 0.25-2 μg/mL). Compounds 10a, 10c, 10e and 10f displayed activity against linezolid resistant Gram-positive organisms (MIC = 2-4 μg/mL). Selected oxazolidinones were evaluated for in vivo efficacy against a mouse systemic infection model.
ANTIPARASITIC COMPOUNDS AND COMPOSITIONS
-
Page/Page column 44, (2010/11/29)
Disclosed is use of a compound having a structure according to general formula (I) defined below, in the manufacture of a medicament to treat and/or prevent a parasitic infection or infestation in a mammalian subject wherein X1 = N or CH or C=O (X2 = NH) or C=S (X2 = NH) or C-OR1 or C-halogen or C-azide; X2 = N or CR1 or C-halogen or CS(O)nR1 where n = 0-2 or a (C)m linker where m = 1-3 between X2 and X6 or C-X5X6 (in which case X5X6 at C6 (purine numbering) is replaced by H or NHR1 or O or OR1 or S or SR1); X3 = N or CH or C-NO2; X4 = N or CH or C-NO2 or C-NR1R2 or an amidine derivative or a guanidinium derivative; X5 = O or NR1 or CR1R2; X6 = OR1 or O-acyl or 0-S(O)nR1 or NR1R2 or NH-acyl or N(Acyl)2 or NH-OS(O)2R1 or NH-S(O)nR1 where n = 0-2 or a hydrazone derivative or an oxime derivative, but if X5 = O, X6 cannot = O or X5X6 is an amidine or an N-substituted pyridine or substituted guanidine; Y = H or NH2 or NR1R2 or -O (X3 = NH) or OR1 or F or Cl or Br or I or CR1R2R3 or S(O)nR1 where n = 0-2 or azide or X5X6 (in which case X5X6 at C6 (purine numbering) is replaced by H or NHR1 or O or OR1 or S or SR1); R1, R2, R3 are independently selected from the group consisting of H or (optionally substituted), alkyl, alkenyl or alkynyl or aryl or aralkyl where the substituents may be selected from H, OH, NH2, halogen, N3, CN, CHO, COOR', C0NR'2, OR, NE'2, SR', NR'NR'2, NR'OR', NO2 and R' is alkyl, alkenyl, alkynyl, aralkyl, acyl, sulfonyl; Z = H or substituted (alkyl or alkenyl or alkynyl or aralkyl) or a sugar derivative of general formula (II) in the β-configuration where: B is the nucleobase from Formula (I); X7 = CH2 or O or NR1 or S; R4 = H or OH or OR1 or halogen or azide or a phosphate derivative; R5 = H or F or CH3; R6 = H or OH or OR1 or halogen or azide or a phosphate derivative; and R7 = H or halogen or R1 or a derivative of an amino acid or PO3H2 or P2O6H3 or P3O9H4 or a methylene derivative of P2O6H3 or P3O9H4 or a masked phosphate or a phosphonate derivative (5'-O replaced with CH2).
Effect of a hydrogen bonding carboxamide group on universal bases
Too, Kathleen,Brown, Daniel M.,Holliger, Philipp,Loakes, David
, p. 899 - 911 (2008/02/03)
A number of aromatic universal base analogues have been described in the literature, but most are non-hydrogen bonding. We have examined the effect of introducing hydrogen bonding carboxamide groups onto the pyrrole ring of 5-nitroindole. The modified ana
