Evaluation of sorghum straw hemicellulosic hydrolysate for xylitol production
Sene,L;Vaz-Arrudaa,Menegati-Oliveiraa,S;Almeida Felipe,M
New Biotechnology
2009, Vol.25(1), pp.S226-S227
DOI: 10.1016/j.nbt.2009.06.196

High specific activity tritium-labeled N-(2-methoxybenzyl)-2,5-dimethoxy-4-iodophenethylamine (INBMeO): A high-affinity 5-HT2A receptor-selective agonist radioligand
David E. Nicholsa,  Stewart P. Frescasa, Benjamin R. Chemela, Kenneth S. Rehderb, Desong Zhongb and Anita H. Lewinb
Bioorganic & Medicinal Chemistry
2008, Volume 16, Issue 11, Pages 6116-6123
doi:10.1016/j.bmc.2008.04.050


Abstract
The title compound ([3H]INBMeO) was prepared by an O,O-dimethylation reaction of a t-BOC protected diphenolic precursor using no carrier added tritiated iodomethane in DMF with K2CO3. Removal of the t-BOC protecting group and purification by HPLC afforded an overall yield of 43%, with a radiochemical purity of 99% and specific activity of 164 Ci/mmol. The new radioligand was suitable for labeling human 5-HT2A receptors in two heterologous cell lines and had about 20-fold higher affinity than [3H]ketanserin.

Copper Catalyzed Arylation/C?C Bond Activation: An Approach toward ?-Aryl Ketones
Chuan He†, Sheng Guo†, Li Huang† and Aiwen Lei
J. Am. Chem. Soc.
2010, 132 (24), pp 8273–8275
DOI: 10.1021/ja1033777

The Persulfate Oxidation of Salicylic Acid 2,3,5-trihydroxybenzoic acid
Schrock,R;Tabern,D
J.Org.Chem
1951, Vol.16(11), pp.1772-1775
DOI: 10.1021/jo50005a018


Abstract
The oxidation of salicylic acid to gentisic acid by persulfate ion has been described (1,2,3). Recently a more complete study of the products of the reaction has revealed in addition to gentisic acid the presence of 2,3-dihydroxybenzoic acid to the extent of 15% of the final product (4). This is apparently the first published report of ortho attack even though the para position was unsubstituted. Prior to this communication ortho substitution was reported only when the para position was blocked.

The Henry reaction: spectroscopic studies of nitrile and hydroxylamine by-products formed during synthesis of psychoactive phenylalkylamines
Michelle Guy, Sally Freeman, John F. Alder and Simon D. Brandt
Central European Journal of Chemistry
2008, Volume 6, Number 4 ,pages 526-534
doi;10.2478/s11532-008-0054-z

Abstract
A clandestine two-step route to psychoactive racemic phenylalkylamines utilises the Henry reaction. In the first step an aromatic aldehyde reacts with a nitroalkane to give the nitrostyrene intermediate. In the second step the nitrostyrene is reduced to the phenylalkylamine. An impurity profile of both steps was evaluated through the synthesis and analysis of common street derivatives. The formation of nitrile impurities in the nitroaldol reaction and hydroxylamine impurities in the reduction step were shown by NMR spectroscopy and GC-MS. A selection of reducing agents has been used to give the phenylalkylamines, together with variable quantities of the partially reduced hydroxylamine product. GC-MS analysis of the hydroxylamines showed heat-induced disproportionation which led to the detection of the corresponding oximes.


Keywords; Drugs of abuse - Impurities - Amphetamines - NMR - GC-MS

Degradation of quaternary ammonium salts. Part VI. Effect of substitution on velocity of intramolecular rearrangement
John Laing Dunn and Thomas Stevens Stevens
J. Chem. Soc.
1932, 1926-1931
DOI: 10.1039/JR9320001926

Degradation of quaternary ammonium salts. Part VII. New cases of radical migration
Thomas Thomson and Thomas Stevens Stevens
J. Chem. Soc.
1932, 1932-1940
DOI: 10.1039/JR9320001932

Synthesis and 5-HT2A Radioligand Receptor Binding Assays of DOMCl and DOMOM, Two Novel 5-HT2A Receptor Ligands
Antje Harmsa, Ernst Ulmerb, Karl-Artur Kovarb
Arch. Pharm. Pharm. Med. Chem. 2003, 336, 155–158 dio:10.1002/ardp.200390014

A synthesis of two new active substances, DOMCl (1-(4-chloromethyl-2, 5-dimethoxyphenyl)-2-propanamine; 2) and DOMOM (1-(2, 5-dimethoxy-4-methoxymethylphenyl)-2-propanamine; 3), was developed. Unexpectedly, the Blanc reaction permitted successful synthesis of 2, 5-dimethoxyphenylpropylamine derivatives having a substituted methyl group in position 4 since solvation of the reactant occurs during the reaction. Afterwards, their affinities towards the 5-HT2A receptor were examined in 5-HT2A radioligand receptor binding assays. The study of these substances is of considerable interest because they were predicted, by preliminary molecular modeling studies based on mescalin units, to be potential new hallucinogens that should be added to the list of substances prohibited by law. It was assumed that DOMCl would be 82 times more potent as a hallucinogen than mescalin, and DOMOM would be 94 times more potent. The 5-HT2A radioligand receptor binding studies showed that the affinities of DOMCl and DOMOM for the 5-HT2A receptor are less than expected but are nevertheless 1.6 and 8.7 times higher, respectively, than that of mescalin. Therefore, scheduling these substances as potential drugs of abuse might be considered.

Keywords
5-HT2A receptor • 5-HT2A radioligand receptor binding assay • DOMCl • DOMOM • Synthesis

@Salat

In vitro dopaminergic neuroprotective and in vivo antiparkinsonian-like effects of ?3,2-hydroxybakuchiol isolated from Psoralea corylifolia (L.)

G. Zhao a, b, X.-W. Zheng a, G.-W. Qin c, Y. Gai a, Z.-H. Jiang a and L.-H. Guo

Journal Cellular and Molecular Life Sciences
ISSN 1420-682X (Print) 1420-9071 (Online)
Issue Volume 66, Number 9 / May, 2009 Pages 1617-1629
DOI 10.1007/s00018-009-9030-9


Abstract

Cocktail recipes containing Psoralea corylifolia seeds (PCS) are used to empirically treat Parkinson disease. A PCS isolate ?3,2-hydroxybakuchiol (BU) can inhibit dopamine uptake in dopamine transporter (DAT) transfected Chinese hamster ovary (CHO) cells, and dopamine reuptake blockade may provide an alternative approach for ameliorating parkinsonism. Here, we assessed the potential dopaminergic neuroprotective, and antiparkinsonian-like activity of BU. BU sample size was increased by using a scale-up extraction paradigm. Pharmacologically, BU significantly protected SK-N-SH cells from 1-methyl-4-phenylpyridinium (MPP+) insult, produced striking inhibitory actions on dopamine/norepinephrine uptake and WIN35,428 binding in synaptosomes on in vivo administration, and significantly preventing poor performance on rotarod and dopaminergic loss in substantia nigra in 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) mice. BU acts by protecting dopaminergic neurons from MPP+ injury and preventing against MPTP-induced behavioral and histological lesions in the Parkinson’s disease (PD) model, possibly by inhibiting monoamine transporters. These findings suggest that BU could be meaningful in PD treatment.
Keywords.  ?3,2-hydroxybakuchiol - scale-up extraction - dopamine transporter - reuptake inhibitor - Parkinson’s disease




Bakuchiol analogs inhibit monoamine transporters and regulate monoaminergic functions

Gang Zhaoa, b, Shao-Yun Zanga, Xiang-Wei Zhengb, Xiao-Hua Zhangb and Li-He Guoa

Biochemical Pharmacology
Volume 75, Issue 9, 1 May 2008, Pages 1835-1847
DOI:10.1016/j.bcp.2008.01.014

Abstract

Monoamine transporters play key roles in controlling monoamine levels and modulating monoamine reuptake. The objective of the present study was to identify monoamine transporter inhibitors from herbal sources. We discovered that bakuchiol analogs isolated from Fructus Psoraleae inhibited monoamine transporter uptake to differing degrees. The bakuchiol analog, ?3,2-hydroxybakuchiol was the most potent and efficacious reuptake blocker and was thus selected as the candidate target. Monoamine transporter inhibition by ?3,2-hydroxybakuchiol was more selective for the dopamine transporter (DAT) (IC50 = 0.58 ± 0.1 ?M) and norepinephrine transporter (NET) (IC50 = 0.69 ± 0.12 ?M) than for the serotonin transporter (SERT) (IC50 = 312.02 ± 56.69 ?M). ?3,2-Hydroxybakuchiol exhibited greater potency (pEC50 for DAT and NET) than bupropion and exhibited similar efficacy (Emax for DAT and/or NET) to bupropion and GBR12,935. Pharmacokinetically, ?3,2-hydroxybakuchiol competitively inhibited DAT and NET with partial reversibility and occupied cocaine binding sites. Moreover, ?3,2-hydroxybakuchiol counteracted 1-methyl-4-phenylpyridinium-induced toxicity in cells expressing DAT with similar efficacy to GBR12,935. In vivo studies showed that ?3,2-hydroxybakuchiol increased the activity of intact mice and improved the decreased activity of reserpinized mice. In the conditioned place preference test, preference scores in intact mice were unaffected by ?3,2-hydroxybakuchiol treatment. Bakuchiol analogs, especially ?3,2-hydroxybakuchiol, are monoamine transporter inhibitors involved in regulating dopaminergic and noradrenergic neurotransmission and may have represented potential pharmacotherapies for disorders such as Parkinson's disease, depression, and cocaine addiction.

Keywords: Bakuchiol analogs; Monoamine transporter; Dopamine transporter; Norepinephrine transporter; Reuptake inhibitor

@ Tsathoggua

Preparation of alginate beads for floating drug delivery
system: effects of CO2 gas-forming agents

B.Y. Choi a, H.J. Park a,*, S.J. Hwang b, J.B. Park

Abstract
Floating beads were prepared from a sodium alginate solution containing CaCO3 or NaHCO3 as gas-forming agents. The solution was dropped to 1% CaCl2 solution containing 10% acetic acid for CO2 gas and gel formation. The effects of gas-forming agents on bead size and floating properties were investigated. As gas-forming agents increased, the size and floating properties increased. Bead porosity and volume average pore size, as well as the surface and cross-sectional morphology of the beads were examined with Mercury porosimetry and Scanning Electron
Microscopy. NaHCO3 significantly increased porosity and pore diameter than CaCO3. Incorporation of CaCO3 into alginate solution resulted in smoother beads than those produced with NaHCO3. Gel strength analysis indicated that bead strength decreased with increasing gas-forming agent from 9 to 4 N. Beads incorporating CaCO3 exhibited
significantly increased gel strength over control and NaHCO3-containing samples. Release characteristics of riboflavin as a model drug were studied in vitro. Release rate of riboflavin increased proportionally with addition of NaHCO3. However, increasing weight ratios of CaCO3 did not appreciably accelerate drug release. The results of these studies
indicate that CaCO3 is superior to NaHCO3 as a gas forming agent in alginate bead preparations. The enhanced buoyancy and sustained release properties of CaCO3-containing beads make them an excellent candidate for floating drug dosage systems (FDDS). © 2002 Published by Elsevier Science B.V.

Keywords: Alginate bead; Floating bead; Floating drug dosage system (FDDS); Gas-forming agent; NaHCO3; CaCO3

@ no1uno

Amino-Alcohols. II. Homologs and Analogs of Phenylpropanolamine

Hartung,Walter;Munch,James;Deckert,W;Crossley,Frank

J. Am. Chem. Soc.
Vol.52( 1930 pp.3317–3322
DOI: 10.1021/ja01371a046
http://pubs.acs.org/doi/abs/10.1021/ja01371a046

Abstract

The preparation of phenylpropanolamine and its p-methyl derivative by reduction of the corresponding oximino ketones has been described. By employing the same technique, it has been possible to prepare other members of the arylalkanolamine series from phenylethanolamine to phenyloctanolamine. Diphenylethanolamine was prepared by the catalytic reduction of benzoin oxime, both the a- and B-oximes yielding the amino-alcohol melting at 165'C.