The total synthesis of (±)-9-deoxygoniopypyrone (1) from the α-allenic alcohol 2 is described. The synthesis is accomplished in 10 steps with the relative configuration of the three contiguous asymmetric centers being established by the highly diastereoselective formation of the syn-vicinal di...

The structure and absolute configuration of natural 8-epi-9-deoxygoniopypyrone have been confirmed by an efficient and highly diastereoselective synthesis in 15 steps from (S)-mandelic acid with an overall yield of 43%.

Stereoselective syntheses of the bio-active styryllactones goniodiol and 9-deoxygoniopypyrone were accomplished from d-(−)-tartaric acid. The key step involves the elaboration of a γ-hydroxy butyramide to the styryllactones via high yielding stereoselective transformations.

Aggregation of Islet amyloid polypeptide (IAPP) is believed to play a critical role in the pathogenesis of Type II Diabetes Mellitus. In an attempt to gain details on the early events of this process, here we performed MD simulations of the spontaneous assembly of three replicas of human IAPP. S...

The siliques and seeds of Arabidopsis thaliana accumulate a series of glucosinolates containing an alkyl side chain of varying length with a terminal benzoate ester function. The biosynthesis of these unusual nitrogen- and sulfur-containing natural products was investigated by feeding isotopical...

An enzymic transesterification was carried out in a continuously operated fixed bed reactor. The reaction system consisted of immobilized α-chymotrypsin (E.C. 3.4.21.1) catalysing the transfer of the l-phenylalanine radical from the racemic propyl ester to 1,4-butanediol, yielding l-phenylalani...

Optimization of a high-throughput screening hit led to the discovery of a new series of 5-phenoxy-1,3-dimethyl-1H-pyrazole-4-carboxamides as highly potent agonists of TGR5. This novel chemotype was rapidly developed through iterative combinatorial library synthesis. It was determined that in vit...

Highly enantioselective and enantiospecific resolution processes were developed for 2-(3-methoxy-4-methyl-phenyl)-propan-1-ol (VI), 2-(2-methoxy-5-methyl-phenyl)-propan-1-ol (VII), 2-(3,4,5-trimethoxy-phenyl)-propan-1-ol (VIII) and 2-(3-hydroxy-4-methyl-phenyl)-propan-1-ol (XII) via lipase-catal...

A novel series of monoamine reuptake inhibitors, the 1-amino-3-(1H-indol-1-yl)-3-phenylpropan-2-ols, have been discovered by combining virtual and focused screening efforts with design techniques. Synthesis of the two diastereomeric isomers of the molecule followed by chiral resolution of each e...

The SAR of a series of 1-amino-3-(1H-indol-1-yl)-3-phenylpropan-2-ols as monoamine reuptake inhibitors, with a goal to improve both potency toward inhibiting the norepinephrine transporter and selectivity over the serotonin transporter, is reported. The effect of specific substitution on both th...

High-valent Mn species are key intermediates in the oxygen evolving complex in photosystem II. In some mechanisms, the MnVO moiety is proposed to be a critical species at the final step of oxygen production. This work reports the use of a mechanistic probe 2-methyl-1-phenylpropan-2-yl hydroperox...

In this study, the Fourier Transform Infrared (FT-IR) and FT-Raman of (1S,2R)-2-amino-1-phenylpropan-1-ol (abbreviated as 2APPO) have been recorded in the regions 4000-100 cm− 1 and 4000–400 cm− 1, respectively. A complete assignment and analysis of the fundamental vibrational modes of the mole...

Novel N-(1-(4-(dibenzo[b,f][1,4]thiazepin-11-yl)piperazin-1-yl)-1-oxo-3-phenylpropan-2-yl derivatives were designed, synthesized and their chemical structures were confirmed by 1H NMR, 13C NMR and Mass spectra. The anticancer activities of the newly synthesized compounds were evaluated in vitro ...

A class of N,N-dialkylated 4-(4-arylsulfonylpiperazine-1-carbonyl)-benzamidines and 4-((4-arylsulfonyl)-2-oxo-piperazin-1-ylmethyl)-benzamidines has been discovered as potent factor Xa inhibitors with desirable in vitro and in vivo anticoagulant activity, but with low oral bioavailability. The 5...

5-Carboxy-6-chloroindole, a precursor for p38 kinase inhibitor, was prepared from 4-amino-2-chloro-3-iodobenzoicacid by following the Japp–Klingemann synthetic approach. The structures of the key intermediates were also confirmed by X-ray analyses. Computational analysis was helpful in understa...

The use of high-performance liquid chromatography in the reversed-phase mode coupled to a spectrophotofluorimetric detector allowed the selective detection of acidic indoles possessing a C-3 methylene side chain, following the reaction of a purified plant extract with acetic anhydride. Of these ...

The nitrosation rates of indole-3-acetonitrile, indole-3-carbinol, indole and 4-chloroindole and the stability of their nitrosated products were investigated. Each of the nitrosated indole compounds was directly mutagenic to Salmonella typhimurium TA 100 in the following order of potency: 4-chlo...

Cytochrome P450 (P450) 2A6 is able to catalyze indole hydroxylation to form the blue dye indigo. The wild-type P450 2A6 enzyme was randomly mutated throughout the whole open reading frame and screened using 4-chloroindole hydroxylation, a substituted indole selected from 30 indole compounds for ...

Endogenous IAA and 4-chloroindole-3-acetic acid (4-C1-IAA) were analysed in vegetative and reproductive tissues of the garden pea (Pisum sativum) using GC-MS selected ion monitoring in the presence of stable-isotope labelled internal standards. In fruit collected 3–8 days after anthesis (DAA) c...

A series of trihalogenated alkenylbenzenes undergo consecutive palladium catalyzed inter- and intramolecular amination reactions to deliver a series of 1-functionalized mono-chloroindoles. 4-, 5-, 6- and 7-Chloroindoles can all be prepared; carbamates, anilines and amines can be employed as the ...