Synthesis of the Selective 5-Hydroxytryptamine 4 (5-HT4) Receptor Agonist (+)-(S)-2-Chloro-5-methoxy-4-(5-(2-piperidylmethyl)-1,2,4-oxadiazol-3-yl)aniline.

Suzuki, Takeshi; Iwaoka, Kiyoshi; Imanishi, Naoki; Nagakura, Yukinori; Miyata, Kenji; Nakahara, Hideaki; Ohta, Mitsuaki; Mase, Toshiyasu

doi:10.1248/cpb.47.120

Cited by 12 publications

(10 citation statements)

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“…General procedure for the synthesis of 3-phenyl [1,2,4]oxadiazole-5-benzo [1,3]dioxol-5-ylmethylene-carbohydrazide derivatives 4a-h A mixture of O.Olmol of derivative 3a-h and O.Olmol of piperonal in 50mL of THF was refluxed in an inert atmosphere for 4h. Using a not very polar solvent on synthesis, we obtained better yields than those found for analogous compounds.…”

Section: ]-Oxadiazole-5-carboxylic Acid Benzolmentioning

confidence: 99%

“…Then, all solvent was evaporated out and compounds were purified in a flash chromatographic column before being recrystallized from dioxane/water system. [1,3] [1,2,4]oxadiazole-5-benzo [1,3] …”

Section: ]-Oxadiazole-5-carboxylic Acid Benzolmentioning

confidence: 99%

“…Nitro-phenyl[1,2,4]oxadiazole-5-benzo[l, 3]dioxol-5-ylmethylene-carbohydrazide 4d, yield = 94; Mp (°C) = 258-260; IR (υ cm"') = 3304 (N-H), 1712 (C=0), 1591 (C=N), 3095 (C-H); MS (m/z %) = 381 M + (74), 190(22), 162(12), 148(12), 147(100), 134(38)E), 6.02(s, H-9, Z); ratio {E/Z) = 91/9.…”

mentioning

confidence: 99%

“…2,4]oxadiazole-5-benzo[1,3]dioxol-5-ylmethylene-carbohydrazide 4e, yield = 81; Mp (°C) = 241-243; IR (υ cm" 1 ) = 3318 (N-H), 1708 (C=0), 1596 (C=N), 3023 (C-H); MS (m/z %) = 415 M + (24), 417(6), 267(4), 190(17), 162(14), 147(100), 134(39); 'H NMR (δ ppm) = 7.84 (d, H-2, J=8.4Hz), 8.03(d, H-3, J=8.4Hz), 12.64(s, H-4), 8.53(s, H-5 E),…”

mentioning

confidence: 99%

“…2,4]oxadiazole-5-benzo[1,3]dioxol-5-ylmethylene-carbohydrazide 4h, yield = 93; Mp (°C) = 231-233; IR (υ cm -1 ) = 3260 (N-H), 1679 (C=0), 1598 (C=N), 3068 (C-H); MS (m/z %) = 352 M + (7), 351(100), 205(31), 190(7), 162(14), 147(57), 135(11), 134(79); *H NMR (δ ppm) = 10.25(s, H-l), 6.96 (d, H-2, J=8.7Hz), 7.93(d, H-3, J=8.4Hz), 12.65(s, H-4), 8.5l(s, H-5 E), 8.07(s, H-5 Z), 7.32 (d, H-6, J=1.5Hz), 7.22(dd, H-7, J=8, 1.5Hz), 7.01 (d, H-8, J=8.1Hz), 6.1(s, H-9, E), 6.02(s, H-9, Z); ratio {EIZ) = 91/9.…”

mentioning

confidence: 99%

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Synthesis, Biological Evaluation, and Structural Studies of 3-Phenyl[ 1,2,4]oxadiazole-5-Carboxylic Acid Benzo[1,3]dioxol 5-Ylmethylene-Hydrazide

Santos-Filho¹,

Lima²,

Leite³

et al. 2005

Heterocyclic Communications

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A series of 1,2,4-oxadiazole combined with carbohydrazides residues, designed as possible bioactive compounds, was obtained in an attempt to analyse the effects of this molecular hybridization on the biological properties of the resulting compounds. They were tested for their antimicrobial and antimalarial activity. Ab initio calculations were performed in order to strengthen experimental NMR structural data.

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