117752-85-9Relevant academic research and scientific papers
Rational design, synthesis and in vitro evaluation of novel exo-methylene butyrolactone salicyloylamide as NF-κB inhibitor
Sidthipong, Kulrawee,Ma, Jun,Yu, Wei Lin,Wang, Yan Feng,Kobayashi, Susumu,Kishino, Satoshi,Koide, Naoki,Yokochi, Takashi,Kato, Kuniki,Okada, Shoshiro,Umezawa, Kazuo
, p. 562 - 566 (2017/01/17)
(?)-Dehydroxymethylepoxyquinomicin ((?)-DHMEQ, 1) is a specific inhibitor of NF-κB. It binds to SH group in the specific cysteine residue of NF-κB components with its epoxide moiety to inhibit DNA binding. In the present research, we have designed and synthesized an epoxide-free analog called (S)-β-salicyloylamino-α-exo-methylene-?-butyrolactone (SEMBL, 3). SEMBL inhibited DNA binding of NF-κB component p65 in vitro. It inhibited LPS-induced NF-κB activation, iNOS expression, and inflammatory cytokine secretions. It also inhibited NF-κB and cellular invasion in ovarian carcinoma ES-2 cells. Moreover, its stability in aqueous solution was greatly enhanced compared with (?)-DHMEQ. Thus, SEMBL has a potential to be a candidate for a new anti-inflammatory and anticancer agent.
Synthesis of enantiomerically pure β-amino-α-methylene-γ-butyrolactones by way of ozonolysis of aromatic α-amino acids
Hvidt, Torsten,Szarek, Walter A.,Maclean, David B.
, p. 779 - 782 (2007/10/02)
The (R) and (S) isomers of β-amino-α-methylene-γ-butyrolactone hydrochloride (4-amino-dihydro-3-methylene-2(3H)-furanone hydrochloride) have been synthesized from (R)- and (S)-tryptophan, respectively.A key step is the ozonolysis of N,O-diacetyl-2-amino-3-(3'-indolyl)-1-propanol. (S)-β-Amino-α-methylene-γ-butyrolactone hydrochloride has been synthesized also by an analogous route starting with (S)-phenylalanine.
