152467-43-1

Upstream product

• 56856-73-6 3-(4-chlorophenyl)-3-ketopropionaldehyde 
• 104-88-1 4-chlorobenzaldehyde 
• 22027-53-8 methyl 3-(4-chlorophenyl)-3-oxopropanoate 
• 99-91-2 para-chloroacetophenone 
• 1798-84-1 1-chloro-4-cyclopropylbenzene 
• 1073-67-2 4-vinylbenzyl chloride 
• 2881-63-2 ethyl (4-chlorobenzoyl)acetate 
• 70200-14-5 ethyl 3-hydroxy-3-(4-chlorophenyl)propanoate 

Downstream Products

• 171661-84-0 3-(4-chlorophenyl)-3-hydroxypropyl 4-methylbenzenesulfonate 
• 1621176-43-9 1-(4-chlorophenyl)-3-(4,5,6,7-tetrabromo-2H-benzotriazol-2-yl)propan-1-ol 
• 928780-22-7 4-amino-1-{3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-[4-(4-chloro-phenyl)-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yloxymethyl]-tetrahydro-furan-2-yl}-1H-pyrimidin-2-one 

Relevant academic research and scientific papers

Lewis Base-Promoted Ring-Opening 1,3-Dioxygenation of Unactivated Cyclopropanes Using a Hypervalent Iodine Reagent

A facile and effective system has been developed for the regio- and chemoselective ring-opening/electrophilic functionalization of cyclopropanes through C?C bond activation by [bis(trifluoroacetoxy)iodo]benzene with the aid of the Lewis basic promoter p-toluenesulfonamide. The p-toluenesulfonamide-promoted system works well for a wide range of cyclopropanes, resulting in the formation of 1,3-diol products in good yields and regioselectivity.

Synthesis of novel chiral TBBt derivatives with hydroxyl moiety. Studies on inhibition of human protein kinase CK2α and cytotoxicity properties

The efficient method for the synthesis of novel 4,5,6,7-tetrabromo-1H- benzotriazole (TBBt) derivatives bearing a single stereogenic center has been developed. New compounds with a variety of substituents at the meta- and para-position of the phenyl ring are reported. All of the presented compounds were obtained using classical synthetic methods, such as bromination of benzotriazole, and its subsequent alkylation by monotosylated arylpropane-1,3-diols, which in turn have been synthesized through reduction of the corresponding prochiral β-keto esters, and the selective monotosylation of the primary hydroxyl group. The influence of the new and previously reported N-hydroxyalkyl TBBt derivatives on the activity of human protein kinase CK2α catalytic subunit was examined. The most active were derivatives with N-hydroxyalkyl substituents (IC50 in 0.80-7.35 μM range). A binding mode of (R)-1-(4,5,6,7-tetrabromo-2H-benzotriazol-2-yl)butan-3-ol 7b to hCK2α has been proposed based on in silico docking studies. Additionally, MTT-based cytotoxicity tests demonstrated high activities of novel 1-aryl-3-TBBt-propan-1-ol and 3-TBBt-propan-1,2-diol derivatives against human peripheral blood T lymphoblast (CCRF-CEM), and moderate anti-tumor activities against human breast adenocarcinoma (MCF7) cell lines.

Studies on the chemoenzymatic synthesis of (R)- and (S)-methyl 3-aryl-3-hydroxypropionates: The influence of toluene-pretreatment of lipase preparations on enantioselective transesterifications

Two series (para- and meta-substituted) of racemic methyl esters of 3-aryl-3-hydroxypropionic acid were prepared after which the enantiomers were separated by an enzyme-catalyzed transesterification. Several lipases were investigated as the catalyst. The influence of the enzyme pretreatment, as well as substrate concentration, reaction temperature, stirring manner, and substrate conversion on the stereochemical outcome of the biotransformation process were investigated in detail. The best results were achieved by using solvent-pretreated lipase from Pseudomonas fluorescens or Burkholderia cepacia suspended in toluene, and vinyl acetate as the acetyl group donor.

Design, synthesis, and evaluation of novel cyclic phosphates of 5-aminosalicylic acid as cytochrome P450-activated prodrugs

Four novel cyclic phosphates of the anti-inflammatory agent 5-aminosalicylic acid (5-ASA) were designed and synthesized as cytochrome P450 (CYP)-activated prodrugs. These prodrugs can be used for targeting into gut wall, since these types of cyclic phosph

Tandem catalysis by lipase in a vinyl acetate-mediated cross-aldol reaction

The lipase Novozym435 (0.6% w/w) was used in tandem with organocatalysts in a first vinyl/isopropenyl acetate-mediated aldol reaction. The reaction was facilitated through the lipase-catalyzed in situ generation of acetaldehyde/acetone. The important features of the present methodology include the mild and facile reaction conditions, regenerability of the lipase, comparatively high yields and minimal side product formation.

A prodrug approach towards the development of tricyclic-based FBPase inhibitors

For the purpose of reducing the strong CYP3A4 inhibitory potency of diamide prodrug 4, cyclic prodrugs of tricyclic-based FBPase inhibitors were synthesized. Extensive SAR studies led to the discovery of pyridine-containing cyclic prodrug 20, which strong

Reduction of aromatic and aliphatic keto esters using sodium borohydride/MeOH at room temperature: a thorough investigation

Reduction of keto esters is a valuable alternative to produce diols. Sodium borohydride/MeOH system at room temperature and short reaction time efficiently reduced α, β, γ, and δ-keto esters having α-keto esters as the most reactive. The ester functionality was reduced effectively due to the presence of oxo group that somehow facilitates the formation of ring intermediate. As expected, the chemoselective experiments showed that ester functionality was not reduced using this system. This study presents a simple, easy, and benign reduction process of various keto esters to its corresponding diols.

Synthesis and characterization of a novel liver-targeted prodrug of cytosine-1-β-D-arabinofuranoside monophosphate for the treatment of hepatocellular carcinoma

Cytotoxic nucleosides have proven to be ineffective for the treatment of hepatocellular carcinoma (HCC) due, in part, to their inadequate conversion to their active nucleoside triphosphates (NTP) in the liver tumor and high conversion in other tissues. Th

Facile reduction of aromatic aldehydes, ketones, diketones and oxo aldehydes to alcohols by an aqueous TiCl3/NH3 system: Selectivity and scope

A simple and rapid procedure for the almost quantitative reduction of aromatic aldehydes, ketones, diketones and oxo aldehydes to alcohols by use of TiCl3/NH3 in aqueous methanol solution is reported. The reducing system distinguishes between different classes of aldehydes and/or ketones, and many functionalities that usually do not survive under reducing conditions are tolerated well. The concept of reversal of chemoselectivity has also been developed. A mechanism based on two sequential one-electron transfers from TiIII to the carbonyl carbon atom is proposed, the second SET becoming operative only in the presence of ammonium ion (either added or formed in situ). Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.