485809-19-6Relevant articles and documents
New optimized piperamide analogues with potent in vivo hypotensive properties
Duarte, Carolina De Mattos,Verli, Hugo,Araújo-Júnior, Jo?o Xavier De,Medeiros, Isac Almeida De,Barreiro, Eliezer J.,Fraga, Carlos Alberto Manssour
, p. 363 - 369 (2004)
We describe herein the structural optimization of new piperamide analogues, designed from two natural prototypes, piperine 1 and piperdardine 2, obtained from Piper tuberculatum Jacq. (Piperaceae). Molecular modeling studies using semiempirical AM1 method were made in order to establish rational modifications to optimize them by molecular simplification. The targeted compounds (10) and (11) were respectively obtained using benzaldehyde (12) and para-anisaldehyde (13) as starting materials. 1H NMR spectra showed that the target compounds were diastereoselectively obtained as the (E)-isomer, the same geometry of the natural prototypes. These new synthetic amides presented significant hypotensive effects in cardiovascular essays using in vivo methodologies. Compound 11 (N-[5-(4′-methoxyphenyl)-2(E)-pentenoyl] thiomorpholine) showed a potency 10,000 times greater than its prototype 5, evidencing an optimization of the molecular architecture for this class of hypotensive drug candidates.
Synthesis and fungicidal activity study of novel daphneolone analogs with 2,6-dimethylmorpholine
Xu, Gao-Fei,Yang, Xin-Ling,Lei, Peng,Liu, Xi-Li,Zhang, Xue-Bo,Ling, Yun
, p. 555 - 558 (2016/04/26)
A series of novel daphneolone analogs was designed and synthesized on the basis of natural product 1,5-diphenyl-2-penten-1-one (I) from Stellera chamaejasme L. as lead compound, whereby 2,6-dimethylmorpholine moiety was introduced to replace 1-phenyl group. Their structures were confirmed by IR, 1H NMR, and HRMS (ESI) or elemental analysis, 13C NMR for some representative compounds. The two isomers of target compounds were separated and identified by NOESY technique and chemical method. All of the synthesized compounds have been evaluated for anti-plant pathogenic fungi activities. The results showed that some compounds exhibited moderate to good antifungal activities against tested fungi at the concentration of 50 mg/L. Among them, compound 7d, with a 4-bromine-substituted phenyl group and cis-2,6-dimethylmorpholine moiety, displayed best activity with an EC50 of 23.87 μmol/L against Valsa Mali, superior to lead compound I. In addition, preliminary structure-activity relationship analysis indicated that, between two isomers of target compounds, the antifungal activities of the isomer with cis-2,6-dimethylmorpholine were better than the trans-isomer.
An efficient partial reduction of α,β-unsaturated esters using DIBAL-H in flow
Yoshida, Masahito,Otaka, Hiroyuki,Doi, Takayuki
, p. 6010 - 6016 (2015/03/30)
The partial reduction of α,β-unsaturated esters and benzoate derivatives to form the corresponding aldehydes was achieved using a flow reactor system within 1 s at a high flow rate (18 mL min-1) under cryogenic conditions (-97°C). Commercially available diisobutylaluminium hydride (DIBAL-H) was used as the reductant. The desired enals and benzaldehyde derivatives, except for 4-methoxycinnamate and 4-methoxybenzoate, were formed selectively and redox economically in moderate to high yields.
