3284-79-5Relevant articles and documents
Acid activated montmorillonite K-10 mediated intramolecular acylation: Simple and convenient synthesis of 4-chromanones
Begum, Ayisha F.,Balasubramanian, Kalpattu K.,Shanmugasundaram, Bhagavathy
supporting information, (2021/09/13)
3-Aryloxyproionic acids undergo intramolecular cyclization in the presence of AA.Mont.K-10 in toluene under reflux for 30–45 min in good to excellent yields. Phenyl ring bearing various substituents at the ortho, meta, para positions undergo this cyclization reaction. This method involves simple work up and amenable for large scale preparations. The heterogeneous acid treated catalyst can be regenerated and used for up to three cycles with minimum loss of activity.
Efficient and rapid synthesis of phenolic analogs of 4-phenylbutanoic acid using microwave-assisted Michael addition as a key reaction
Iida, Hirokazu,Akatsu, Yusuke,Mizukami, Kazushi,Natori, Sho,Matsukawa, Minako,Takahashi, Kie
supporting information, p. 581 - 585 (2016/07/06)
ABSTRACT: The addition of phenols to acrylonitrile in the presence of aqueous benzyltrimethylammonium hydroxide or tetramethylammonium hydroxide under microwave irradiation yielded the corresponding Michael adducts. The obtained adducts were easily transformed to phenolic analogs of 4-phenylbutanoic acids via the hydrolysis of nitrile groups.
Design and synthesis of HIV-1 protease inhibitors for a long-acting injectable drug application
Kesteleyn, Bart,Amssoms, Katie,Schepens, Wim,Hache, Geerwin,Verschueren, Wim,Van De Vreken, Wim,Rombauts, Klara,Meurs, Greet,Sterkens, Patrick,Stoops, Bart,Baert, Lieven,Austin, Nigel,Wegner, J?rg,Masungi, Chantal,Dierynck, Inge,Lundgren, Stina,J?nsson, Daniel,Parkes, Kevin,Kalayanov, Genadiy,Wallberg, Hans,Rosenquist, ?sa,Samuelsson, Bertil,Van Emelen, Kristof,Thuring, Jan Willem
, p. 310 - 317 (2013/02/25)
The design and synthesis of novel HIV-1 protease inhibitors (PIs) (1-22), which display high potency against HIV-1 wild-type and multi-PI-resistant HIV-mutant clinical isolates, is described. Lead optimization was initiated from compound 1, a Phe-Phe hydroxyethylene peptidomimetic PI, and was directed towards the discovery of new PIs suitable for a long-acting (LA) injectable drug application. Introducing a heterocyclic 6-methoxy-3-pyridinyl or a 6-(dimethylamino)-3-pyridinyl moiety (R3) at the para-position of the P1′ benzyl fragment generated compounds with antiviral potency in the low single digit nanomolar range. Halogenation or alkylation of the metabolic hot spots on the various aromatic rings resulted in PIs with high stability against degradation in human liver microsomes and low plasma clearance in rats. Replacing the chromanolamine moiety (R1) in the P2 protease binding site by a cyclopentanolamine or a cyclohexanolamine derivative provided a series of high clearance PIs (16-22) with EC50s on wild-type HIV-1 in the range of 0.8-1.8 nM. PIs 18 and 22, formulated as nanosuspensions, showed gradual but sustained and complete release from the injection site over two months in rats, and were therefore identified as interesting candidates for a LA injectable drug application for treating HIV/AIDS.
