Crystal structure of rac-3-[2,3-bis(phenylsulfanyl)-3H-indol-3-yl]propanoic acid
نویسندگان
چکیده
The title compound, C23H19NO2S2, was obtained as an unexpected regioisomer from an attempted synthesis of an inter-mediate for a substituent-effect study on ergot alkaloids. This is the first report of a 1H-indole mono-thio-ating at the 2- and 3-positions to give a 3H-indole. In the crystal, the acid H atom is twisted roughly 180° from the typical carb-oxy conformation and forms centrosymmetric O-H⋯N hydrogen-bonded dimers with the indole N atom of an inversion-related mol-ecule. Together with a weak C-H⋯O hydrogen bond involving the carbonyl O atom, chains are formed along [100].
منابع مشابه
Synthesis, Characterization and Antimicrobial Activity of New 2-Phenylquinoline-4(3H)-one Derivatives
Quinazolinones is an important chemical synthesis with different physiological significance and pharmacological utility. Reaction of anthranilic acid with benzoyl chloride in pyridine yielded 2-phenyl4H-benzo[d][1,3]oxazin-4-one, which on condensation reaction with the tryptophan in glacial acetic acid afforded 3-(1H-indol-3-yl)-2-(4-oxo-2-phenylquinazolin-3(4H)-yl) propanoic acid (2). Treatmen...
متن کاملSonogashira diversification of unprotected halotryptophans, halotryptophan containing tripeptides; and generation of a new to nature bromo-natural product and its diversification in water† †Electronic supplementary information (ESI) available: Experimental procedures; NMR characterisation; LC-MS characterisation. See DOI: 10.1039/c6sc04423a Click here for additional data file.
Experimental For the synthesis of: Sodium 2'-(Dicyclohexylphosphanyl)-2,6-diisopropyl-(1,1-biphenyl)-4-sulfonate (sXPhos) 12 4 Standard Reaction Procedure of 5-bromoindole 15 under reflux: 5 Microwave Reaction Procedure of 5-bromoindole 15: 5 Standard Microwave Reaction Procedure for Tryptophans: 5 (S)-2-Amino-3-(5-(phenylethynyl)-1H-indol-3-yl)propanoic acid 19 6 (S)-2-Amino-3-5-((3-fluorophen...
متن کاملSeven 3-methylidene-1H-indol-2(3H)-ones related to the multiple-receptor tyrosine kinase inhibitor sunitinib.
The solid-state structures of a series of seven substituted 3-methylidene-1H-indol-2(3H)-one derivatives have been determined by single-crystal X-ray diffraction and are compared in detail. Six of the structures {(3Z)-3-(1H-pyrrol-2-ylmethylidene)-1H-indol-2(3H)-one, C(13)H(10)N(2)O, (2a); (3Z)-3-(2-thienylmethylidene)-1H-indol-2(3H)-one, C(13)H(9)NOS, (2b); (3E)-3-(2-furylmethylidene)-1H-indol...
متن کامل4-Nitro-N-phthalyl-l-tryptophan
THE CRYSTAL STRUCTURE OF THE TITLE COMPOUND [SYSTEMATIC NAME: (2R)-3-(1H-indol-3-yl)-2-(4-nitro-1,3-dioxoisoindolin-2-yl)propanoic acid], C(19)H(13)N(3)O(6), an analogue of epigenetic modulator RG108, is constrained by strong hydrogen bonds between the indole N-H group and a carbonyl O atom of the phthalimide ring of a symmetry-related mol-ecule, and between the protonated O atom of the carboxy...
متن کامل3-(7-Methoxy-β-carbolin-1-yl)propionic acid monohydrate
In the title compound, C(15)H(14)N(2)O(3)·H(2)O [systematic name: 3-(7-meth-oxy-9H-pyrido[3,4-b]indol-1-yl)propanoic acid monohydrate], the fused rings make dhedral angles of 0.4 (1), 1.1 (2) and 1.4 (2)°. In the crystal, the water mol-ecule is involved in the formation of three independent hydrogen-bonded chains via O-H⋯O and N-H⋯O hydrogen bonds, while the carb-oxy group forms an inter-molecu...
متن کامل