- Synthesis of highly fluorescent and water soluble perylene bisimide
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Designed and synthesized a new highly water soluble N,N′-bis(2-((5- ((dimethylamino)methyl)furan-2-yl)methylthio)ethyl)perylene-3,4,9, 10-tetracarboxylic diimide from 2-((5-((dimethylamino)methyl)furan-2-yl) methylthio)ethanamine and perylene-3,4,9,10-tetracarboxylic dianhydride. The compound was characterized by 1H, 13C, 2D NMR, mass and IR techniques. The compound is highly fluorescent with good solubility in water and other polar solvents.
- Boobalan, Gopal,Imran, Predhanekar Mohamed,Nagarajan, Samuthira
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Read Online
- Targeting a dynamic protein-protein interaction: Fragment screening against the malaria myosin a motor complex
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Motility is a vital feature of the complex life cycle of Plasmodium falciparum, the apicomplexan parasite that causes human malaria. Processes such as host cell invasion are thought to be powered by a conserved actomyosin motor (containing myosin A or myoA), correct localization of which is dependent on a tight interaction with myosin A tail domain interacting protein (MTIP) at the inner membrane of the parasite. Although disruption of this protein-protein interaction represents an attractive means to investigate the putative roles of myoA-based motility and to inhibit the parasitic life cycle, no small molecules have been identified that bind to MTIP. Furthermore, it has not been possible to obtain a crystal structure of the free protein, which is highly dynamic and unstable in the absence of its natural myoA tail partner. Herein we report the de novo identification of the first molecules that bind to and stabilize MTIP via a fragment-based, integrated biophysical approach and structural investigations to examine the binding modes of hit compounds. The challenges of targeting such a dynamic system with traditional fragment screening workflows are addressed throughout.
- Douse, Christopher H.,Vrielink, Nina,Wenlin, Zhang,Cota, Ernesto,Tate, Edward W.
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- Reductive Amination, Hydrogenation and Hydrodeoxygenation of 5-Hydroxymethylfurfural using Silica-supported Cobalt- Nanoparticles
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Efficient and selective conversion of renewable feedstocks to essential chemicals and fuels applying green and sustainable catalytic processes is of central importance and attracts scientific interest. Among different biomass-based feedstocks, 5-hydroxymethylfurfural (HMF) represents valuable platform compound widely used for the synthesis of valuable chemicals, fuels, and polymers. Here we report cobalt nanoparticles catalyzed reductive amination, hydrogenation and hydrodeoxygenation of HMF to produce furan based primary, secondary and tertiary amines including N-methylamines as well as 2,5-bis(hydroxymethyl)furan, (5-methylfuran-2-yl)methanol and selected N-, O-, and S-containing heterocycles. Key to success for this HMF valorization is the use of reusable silica supported cobalt-based nanoparticles, which have been prepared by the immobilization and pyrolysis of Co-terephthalic acid-piperazine MOF template on silica.
- Chandrashekhar, Vishwas G.,Natte, Kishore,Alenad, Asma M.,Alshammari, Ahmad S.,Kreyenschulte, Carsten,Jagadeesh, Rajenahally V.
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- Versatile CO-assisted direct reductive amination of 5-hydroxymethylfurfural catalyzed by a supported gold catalyst
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Reductive amination (RA) constitutes an attractive and practical strategy for discovering protocols capable of converting biomass into valuable N-containing compounds. Described herein is a versatile and sustainable RA of 5-hydroxymethyl-furfural (HMF), an important biomass-derived aldehyde, using abundant and cheaply available CO and water as reductants. A single phase rutile titania supported gold (Au/TiO2-R) catalyst is shown to efficiently catalyze this CO/H2O-mediated RA under mild and convenient conditions. With this system, a broad spectrum of primary and secondary amines can be used as suitable substrates and the desired reaction can proceed favourably in a highly chemoselective, efficient and atom-economical fashion. In particular, this protocol can also allow convenient access to bis(hydroxylmethylfurfuryl)-amines, a new group of furan-based monomers with great potential to form functional biopolymers with tunable properties. Moreover, this CO-assisted RA is more efficient (higher TON and TOF) and more eco-friendly (increased resource efficiency) than the previous state-of-the-art technique.
- Zhu, Ming-Ming,Tao, Lei,Zhang, Qi,Dong, Jing,Liu, Yong-Mei,He, He-Yong,Cao, Yong
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p. 3880 - 3887
(2017/08/22)
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- 4 β-nitrogen substituted [...] amine podophyllotoxin derivative and its preparation method and application
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The invention provides a 4beta-nitrogen-substituted furan tertiary amine podophyllotoxin derivative. The structural general formula of the derivative is as shown in the specification. The compound is good in solubility and strong in anti-tumor activity and has an obvious suppression effect on the tumor cells such as lung cancer, malignant lymphoma, acute leukemia and the like. The invention also provides a preparation method of the compound.
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Paragraph 0077-0078
(2016/11/28)
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- Synthesis and biological evaluation of ranitidine analogs as multiple-target-directed cognitive enhancers for the treatment of Alzheimer's disease
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Using molecular modeling and rationally designed structural modifications, the multi-target structure–activity relationship for a series of ranitidine analogs has been investigated. Incorporation of a variety of isosteric groups indicated that appropriate aromatic moieties provide optimal interactions with the hydrophobic and π–π interactions with the peripheral anionic site of the AChE active site. The SAR of a series of cyclic imides demonstrated that AChE inhibition is increased by additional aromatic rings, where 1,8-naphthalimide derivatives were the most potent analogs and other key determinants were revealed. In addition to improving AChE activity and chemical stability, structural modifications allowed determination of binding affinities and selectivities for M1–M4 receptors and butyrylcholinesterase (BuChE). These results as a whole indicate that the 4-nitropyridazine moiety of the JWS-USC-75IX parent ranitidine compound (JWS) can be replaced with other chemotypes while retaining effective AChE inhibition. These studies allowed investigation into multitargeted binding to key receptors and warrant further investigation into 1,8-naphthalimide ranitidine derivatives for the treatment of Alzheimer's disease.
- Gao, Jie,Midde, Narasimha,Zhu, Jun,Terry, Alvin V.,McInnes, Campbell,Chapman, James M.
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p. 5573 - 5579
(2016/11/09)
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- Synthesis and evaluation of novel podophyllotoxin derivatives as potential antitumor agents
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Cancer multidrug resistance (MDR) is a common cause of treatment failure in cancer patients. Increased expression of permeability glycoprotein (P-gp), which is also known as MDR-1, is the main cause of multidrug resistance. Podophyllotoxin derivatives hold great promise in the battle to overcome multidrug resistance, as they can induce cytotoxicity through multiple mechanisms. Here, we synthesized sixteen novel podophyllotoxin derivatives and evaluated their cytotoxicities in human cancer cell lines, HeLa, K562 and K562/A02. Some of these compounds were more potent than etoposide, a clinically relevant inhibitor of DNA repair enzymes. In particular, compound 5p exhibited the most potent activity toward drug-resistant K562/A02 cells, as it robustly inhibited tumor cell proliferation and induced apoptosis. Furthermore, preliminary investigation suggested that 5p inhibited the expression of MDR-1 in K562/A02 cells more effectively than etoposide.
- Cheng, Wei-Hua,Cao, Bo,Shang, Hai,Niu, Cong,Zhang, Li-Ming,Zhang, Zhong-Heng,Tian, Dan-Li,Zhang, Shi,Chen, Hong,Zou, Zhong-Mei
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p. 498 - 507
(2014/09/16)
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- PREPARATION OF AMINOMETHYL FURANS AND ALKOXYMETHYL FURAN DERIVATIVES FROM CARBOHYDRATES
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Described herein are single step methods of making various classes of alkylamine derivatives of furan and tetrahydrofuran by simultaneous contact of a sugar with H2, an acid catalyst and hydrogenation catalyst in the presence of an alkylamide solvent. The hydrogenation catalyst is a heterogeneous catalyst comprising a metal selected from the group consisting of Pt, Pd, and nickel. The acid catalysts may be homogeneous mineral acid or a heterogeneous acid catalyst on substrate. In a preferred practice the two catalysts are provided on a common heterogeneous bifunctional support. Using similar combinations of acid and hydrogenation catalysts, there is also described single step methods for making furandimethanol by simultaneously contacting a hexose with the two separate catalysts in the presence of H2 in an aprotic solvent, such as dimethylformamide. With the same catalyst system and similar reaction conditions, 2, 5 furan dialkylethers can also be made in a single step when the solvent includes an ROH alcohol.
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Page/Page column 11
(2012/06/30)
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- PIPERIDINE DERIVATIVES AND METHODS OF USE THEREOF
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The present invention relates to Compounds of Formula (I), compositions comprising the compounds, and methods of using the compounds to treat or prevent pain, diabetes, a diabetic complication, impaired glucose tolerance (IGT) or impaired fasting glucose (IFG) in a patient.
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Page/Page column 76
(2008/12/08)
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- QUINAZOLINE DERIVATIVES,PREPARATION METHODS AND USES THEREOF
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The present invention has disclosed a compound of formula I and a pharmaceutically acceptable salt or a solvate thereof, wherein the substituents are as defined in the description. The invention has also disclosed a method for preparing the compound of formula I, the pharmaceutical compositions comprising the same and their uses in the preparation of an anti- tumor medicament.
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Page/Page column 19-20
(2008/12/08)
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- Quinazoline Derivatives, Preparation Methods and Uses Thereof
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The present invention has disclosed a compound of formula I and a pharmaceutically acceptable salt or a solvate thereof, wherein the substituents are as defined in the description. The invention has also disclosed a method for preparing the compound of formula I, the pharmaceutical compositions comprising the same and their uses in the preparation of an anti-tumor medicament.
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Page/Page column 11
(2009/01/20)
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- 2-SACCHARINYLMETHYL ARYL CARBOXYLATES USEFUL AS PROTEOLYTIC ENZYME INHIBITORS AND COMPOSITIONS AND METHOD OF USE THEREOF
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A compound having the formula: STR1 wherein Ar, R 4 and R 5 are defined herein have pharmaceutical utility as proteolytic enzyme inhibitors.
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- Synthesis and pharmacology of two new histamine receptor antagonists related to ranitidine
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Pyridyl and 1,6-dihydropyridyl ranitidine analogues 1 and 2 were obtained by applying an improved modification of ranitidine synthesis. Compound 1 shows a selective H2 antagonistic activity while compound 2 is a non-selective histamine antagonist.
- Navarro,Almeida,Anaya,Moran,Grande,Caballero,Palacios,Montero,San Roman
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- Cholinergic agents structurally related to furtrethonium. 1
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A series of 5-substituted-2-(dimethylaminomethyl)-furyl derivatives 4 was prepared, with the aim of discovering novel antimuscarinic agents which are selective for smooth muscle as opposed to cardiac tissue.Both non-quaternary and quaternary ammonium compounds were synthesised.The agonist starting point, furtrethonium 3, was gradually transformed into antagonist by introduction of lipophilic and bulky groups in position 5 of this molecule.In particular, the introduction of α-hydroxy-α-cyclohexylbenzyl moiety (compound 9b), a lipophilic group characteristic ofantimuscarinic agents, caused an appreciable increase of the antagonist's potency, and the lengthening of the distance between this lipophilic group and the furan ring, obtained by introduction of an ester, ether or amide group, led to some selectivity towards smooth muscle (compounds 19, 21, 25).Interestingly, compound 19, with an ester moiety as a spacer group, proved to be at least 20 times more potent in rat ileum (pKB = 7.3) and rat bladder (pKB = 7.2) than guinea-pig atria (pKB = 5.9). furtrethonium derivatives / cholinergic agents / antimuscarinic activity
- Manfredini, S.,Guarneri, M.,Simoni, D.,Grana, E.,Boselli, C.,et al.
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p. 153 - 162
(2007/10/02)
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- Effects of temperature and relative humidity on the solid-state chemical stability of ranitidine hydrochloride
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The chemical stability of ranitidine HCl in solution and in the solid state at various temperatures was investigated by high-performance liquid chromatography. Ranitidine HCl was unstable in lower pH buffer solutions, and the percent degradation after 72 h increased as the pH of the buffer solution was reduced. The percent degradation in the unbuffered solution increased dose dependently. The critical relative humidity (CRH) of the ranitidine HCl bulk powder was ~67% relative humidity (RH). The amount of water adsorbed onto the sample above the CRH was proportional to the RH level. The percent degradation of the powder below 50% RH was almost negligible because, at this level, it was a solid. The percent degradation at 60-70% RH was higher than that above 70% RH. Ranitidine HCl powder was unstable around the CRH.
- Teraoka,Otsuka,Matsuda
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p. 601 - 604
(2007/10/02)
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- Isolation and Identification of the Hydrolytic Degradation Products of Ranitidine Hydrochloride
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Hydrolytic degradative studies on ranitidine hydrochloride (1) have shown that two different pathways are operative under strongly acid and strongly alkaline conditions.At intermediate pH values both pathways are operative whilst at very low pH values ranitidine hydrochloride is resistant to hydrolytic cleavage.This resistance to hydrolysis may be ascribed to C- protonation of the enediamine.
- Haywood, Phillip A.,Martin-Smith, Michael,Cholerton, Trevor J.,Evans, Michael B.
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p. 951 - 954
(2007/10/02)
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- Process for preparing thieno-fused heterocyclic anti-ulcer agents
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A process for preparing certain thieno-fused heterocyclic compounds having H2 -receptor antagonist and antisecretory activity, which comprises reacting a suitable thienoisothiazole derivative with an appropriate (furanylmethylthio)ethanamine derivative to yield an intermediate, which is subjected to cyclization to yield the desired final product.
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- Process for preparing thieno-fused heterocyclic anti-ulcer agents and intermediates therefor
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A process for preparing certain thieno-fused heterocyclic compounds having H2 -receptor antagonist and antisecretory activity, which involves the reaction of a mercaptan, obtained by reduction of a thienoisothiazole amino alkyl disulfide, with a 5-substituted-2-furanylmethanol; and said thienoisothiazole amino alkyl disulfide intermediates.
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- Process for the preparation of 5-dimethylaminomethyl-2-furanmethanol
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A process for preparing 5-dimethylaminomethyl-2-furanmethanol by reacting 2-furanmethanol with bis(dimethylamino)methane. The product is useful as a chemical intermediate, in particular to prepare H2 -histamine antagonists.
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