67852-95-3

Upstream product

• 18520-63-3 monobenzyl terephthalate 
• 100-39-0 benzyl bromide 
• 619-66-9 4-Carboxybenzaldehyde 
• 78767-55-2 benzyl 4-formylbenzoate 
• 19851-61-7 p-dibenzyl benzenedicarboxylate 
• 100-21-0 terephthalic acid 
• 100-20-9 terephthaloyl chloride 

Downstream Products

• 101097-45-4 4-benzyloxycarbonyl-benzamide 
• 122335-18-6 1,2-bis-(4-benzyloxycarbonyl-benzoyloxy)-ethane 
• 159157-21-8 (R,S)-1,6-di(benzoyloxy)-4,4'-di(benzyloxycarbonyl)-3-methylhexane 
• 121866-12-4 benzyl 4-<(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-1H-benzindol-1-yl)carbonyl>benzoate 
• 153849-52-6 N-Ethoxycarbonylmethyl-N-phenyl-terephthalamic acid benzyl ester 
• 126657-59-8 3-nitrophenyl 4-(4-octyloxyphenoxycarbonyl)benzoate 
• 154741-26-1 1-chloroethyl 4-(benzyloxycarbonyl)benzoate 
• 1365797-39-2 N-(4-benzyloxycarbonylbenzoyl)-N'-β-D-glucopyranosylurea 
• 1365797-41-6 N-(4-carboxybenzoyl)-N'-β-D-glucopyranosylurea 
• 153849-61-7 N-Ethoxycarbonylmethyl-N-phenyl-terephthalamic acid 

Relevant academic research and scientific papers

Design, synthesis, and biological evaluation of novel matrix metalloproteinase inhibitors as potent antihemorrhagic agents: From hit identification to an optimized lead

Growing evidence suggests that matrix metalloproteinases (MMP) are involved in thrombus dissolution; then, considering that new therapeutic strategies are required for controlling hemorrhage, we hypothesized that MMP inhibition may reduce bleeding by delaying fibrinolysis. Thus, we designed and synthesized a novel series of MMP inhibitors to identify potential candidates for acute treatment of bleeding. Structure-based and knowledge-based strategies were utilized to design this novel chemical series, α-spiropiperidine hydroxamates, of potent and soluble (>75 μg/mL) pan-MMP inhibitors. The initial hit, 12, was progressed to an optimal lead 19d. Racemic 19d showed a remarkable in vitro phenotypic response and outstanding in vivo efficacy; in fact, the mouse bleeding time at 1 mg/kg was 0.85 min compared to 29.28 min using saline. In addition, 19d displayed an optimal ADME and safety profile (e.g., no thrombus formation). Its corresponding enantiomers were separated, leading to the preclinical candidate 5 (described in Drug Annotations series, J. Med. Chem. 2015, 10.1021/jm501939z).

Synthesis of benzoic acids and polybenzamides containing tertiary alkylamino functionality

The high-yielding and easily scalable synthesis of a number of benzoic acids bearing a tertiary alkylamino functionality has been achieved. The flexible synthesis began from readily available aminobenzoic acids or terephthaloyl chloride and requires almost no chromatography. Coupling of the synthesised amino acids to a range of substituted anilines was achieved when utilizing a specific combination of DIC, HOBt and DMAP.

N-(4-Substituted-benzoyl)-N′-(β-d-glucopyranosyl)ureas as inhibitors of glycogen phosphorylase: Synthesis and evaluation by kinetic, crystallographic, and molecular modelling methods

N-(4-Substituted-benzoyl)-N′-(β-d-glucopyranosyl) ureas (substituents: Me, Ph, Cl, OH, OMe, NO2, NH2, COOH, and COOMe) were synthesised by ZnCl2 catalysed acylation of O-peracetylated β-d-glucopyranosyl urea as well as in reactions of O-peracetylated or O-unprotected glucopyranosylamines and acyl-isocyanates. O-deprotections were carried out by base or acid catalysed transesterifications where necessary. Kinetic studies revealed that most of these compounds were low micromolar inhibitors of rabbit muscle glycogen phosphorylase b (RMGPb). The best inhibitor was the 4-methylbenzoyl compound (Ki = 2.3 μM). Crystallographic analyses of complexes of several of the compounds with RMGPb showed that the analogues exploited, together with water molecules, the available space at the β-pocket subsite and induced a more extended shift of the 280s loop compared to RMGPb in complex with the unsubstituted benzoyl urea. The results suggest the key role of the water molecules in ligand binding and structure-based ligand design. Molecular docking study of selected inhibitors was done to show the ability of the binding affinity prediction. The binding affinity of the highest scored docked poses was calculated and correlated with experimentally measured Ki values. Results show that correlation is high with the R-squared (R2) coefficient over 0.9.

An efficient route to the synthesis of symmetric and asymmetric diastereomerically pure fullerene triads

A new synthetic route based on the stepwise functionalisation of fullerene cages allows the facile formation of linear, diastereomerically pure triads incorporating two different fullerene cages linked by an organic spacer group. The critical coupling step of two fullerene cages via activation by N,N′-dicyclohexylcarbodiimide was systematically investigated to reveal that the yield of the coupling is maximised in o-dichlorobenzene at high concentrations of the reactant fullerene nucleophile, while in more polar solvents or at lower concentrations of reactants the formation of unwanted side-products (such as guanidine-, N-acylurea- and anhydride-functionalised fullerenes) is favoured. The resultant triads possess an atypically good solubility for this class of compound, which enabled full detailed characterisation by 1H and 13C NMR, IR and UV-vis spectroscopies and by MALDI-TOF mass spectrometry.

Synthesis and protein kinase C inhibitory activities of balanol analogues with modification of 4-hydroxybenzamido moiety

A series of racemic balanol analogues with modification of the benzamido moiety of balanol have been synthesized and evaluated for their inhibitory activities against human protein kinase C isozymes (PKC-alpha, -beta I, -beta II, -gamma, -delta, -epsilon, and -eta). The structural modification includes replacement of the 4-hydroxyphenyl group with variously substituted phenyl rings, substitution of the amide linkage with a sulfonamide or an ester, and replacement of the 4-hydroxyphenyl substructure with a hydroxyl substituted indole or a hydroxybenzyl group. In general, these analogues were found to be less potent than balanol, but a number of analogues were identified with improved isozyme selectivity. The structure-activity relationship studies of these analogues also indicated that (1) the optimal general PKC inhibition requires a free 4-hydroxyl group in the benzamido portion of the molecule, (2) the amide linkage of the benzamido moiety is important for PKC inhibition, and (3) the conformation associated with the benzamido moiety seems to have a profound effect on PKC inhibition. The requirement of a free 4-hydroxyl group in conjunction with an appropriate conformation of the benzamido moiety for optimal PKC inhibition suggests that the 4-hydroxyphenyl group may be involved in a specific inhibitor-enzyme interaction important for PKC inhibition.

Liquid Crystalline Properties of 4-Alkoxyphenyl 4-Thiocyanatophenyl Terephthalates

This paper describes the preparation and thermal properties of a homologous series of 4-alkoxyphenyl 4-thiocya natophenyl terephthalates. The homologous series shows nematic and smectic A phases commencing from the pentyloxy homolog. The smectic A phase i

New Orally Active Serine Protease Inhibitors: Structural Requirements for Their Good Oral Activity

Synthesis and structural requirements for good oral activity of a series of para-substituted benzoyl esters of 4-hydroxybenzamidine serine protease inhibitors are described.The structure required for good oral activity was found to be general formula II w

SYNTHESIS AND LIQUID-CRYSTALLINE PROPERTIES OF NEW CHIRAL POLYESTERS WITH AROMATIC TRIAD MESOGEN AND SPACER OF DIFFERENT OPTICAL PURITY

A series of new chiral liquid-crystalline polyesters 1-x, comprising a terephthalate-methylhydroquinone-terephthalate mesogen and an (R)-3-methyl-1,6-hexanediyl spacer segment of varying optical purity, x (0, 20, 50, 70, or 95percent) has been prepared and studied with respect to the thermotropic properties.The polyesters were synthesized by direct polycondensation of a diacid and a diphenol in pyridine solution at 120 deg C in the presence of p-tosyl chloride as a condensing agent and dimethylformamide as an activator.High molecular weights (Mw = 61,000-73,000, by SEC) and narrow molecular weight distributions (Mw/Mn = 1.1-2.4) were obtained for all of the polyesters.Depending on the optical purity of the spacer, a nematic or a chiral nematic mesophase was formed that extended over a very broad range between the glass and the isotropization temperatures (Tg-Ti >= 179 deg C).X-Ray diffraction patterns proved the chiral mesophase to remain frozen-in in the glassy state.Polyesters 1-x appear to be suitable candidates for electro-optical investigations in the unwound chiral nematic mesophase.

Molecular structure and smectic properties. Part 1. The effect of linkages on smectic A thermal stability in three aromatic ring compounds linked by ester groups

The thermal properties of phenyl 4-(4-alkoxybenzoyloxy)benzoates (1), 4-alkoxyphenyl 4-benzoyloxybenzoates (2), 4-(4-alkoxybenzoyloxy) benzoyloxyxylenes (3), and phenyl 4-(4-alkoxyphenoxycarbonyl)benzoates (4) have been examined. In spite of the structural similarity, the smectic nature of the series is quite different. Series (1) shows a stable smectic A phase starting with the hexyloxy homologue. Series (2) and (3) do not show any smectic phases, and the potential smectic stabilities evaluated from the binary phase diagrams are quite low. Although series (4) shows no smectic phase because of higher melting points, this series intrinsically possesses a smectic A nature, where the potential smectic A - nematic transition temperatures are as high as those of series (1). The difference in the smectic nature for these four series is discussed in terms of the geometrical and electrocstatic properties of the molecules, and a new basis for the thermal stability of the smectic A phase has been proposes.

Thermal and X-Ray Diffraction Studies of Some Liquid Crystals Having a Nitro Group at the Lateral Position

3-Nitrophenyl 4-(4-octyloxy- and 4-(4-nonyloxybenzoyloxy)-benzoates (compound 1), 4-(4-octyloxyphenoxycarbonyl)phenyl 3-nitrobenzoate (compound 2), 4-(4-octyloxy- and 4-(4-decyloxybenzoyloxy)phenyl 3-nitrobenzoates (compound 3), and 3-nitrophenyl 4-(4-octyloxy- and 4-(4-nonyloxyphenoxycarbonyl)benzoates (compound 4) have been prepared.All the compounds show smectic A and nematic phases, where the molecular arrangement in the smectic A phase is dependent on the orientation of the ester linkages.The smectic A phase for compounds 1 and 3 has a monolayer rearrangement of the molecules, while the smectic A phase for compound 3 also involves a small contribution of a partially bilayer nature near the smectic A-nematic transition.The smectic A phase for compound 2 has a bilayer arrangement, and compounds 4 probably the bilayer one.A dipole correlation within the smectic A phases has been discussed. - Keywords: polar liquid crystals; smectic A modification; x-ray diffraction; lateral substituent effect.