Tag: 100-200

Imidazo[1,2-a]pyrazine diaryl ureas: Inhibitors of the receptor tyrosine kinase EphB4 was written by Mitchell, Scott A.;Danca, Mihaela Diana;Blomgren, Peter A.;Darrow, James W.;Currie, Kevin S.;Kropf, Jeffrey E.;Lee, Seung H.;Gallion, Steven L.;Xiong, Jin-Ming;Pippin, Douglas A.;DeSimone, Robert W.;Brittelli, David R.;Eustice, David C.;Bourret, Aaron;Hill-Drzewi, Melissa;Maciejewski, Patricia M.;Elkin, Lisa L.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2009.Quality Control of 3-Cyanophenylisocyanate This article mentions the following:

Inhibition of receptor tyrosine kinases (RTKs) such as vascular endothelial growth factor receptors (VEGFRs) and platelet-derived growth factor receptors (PDGFRs) has been validated by recently launched small mols. Sutent and Nexavar^, both of which display activities against several angiogenesis-related RTKs. EphB4, a receptor tyrosine kinase (RTK) involved in the processes of embryogenesis and angiogenesis, has been shown to be aberrantly up regulated in many cancer types such as breast, lung, bladder and prostate. We propose that inhibition of EphB4 in addition to other validated RTKs would enhance the anti-angiogenic effect and ultimately result in more pronounced anti-cancer efficacy. Herein we report the discovery and SAR of a novel series of imidazo[1,2-a]pyrazine diarylureas that show nanomolar potency for the EphB4 receptor, in addition to potent activity against several other RTKs. In the experiment, the researchers used many compounds, for example, 3-Cyanophenylisocyanate (cas: 16413-26-6Quality Control of 3-Cyanophenylisocyanate).

3-Cyanophenylisocyanate (cas: 16413-26-6) belongs to esters. Carboxylic acid esters of low molecular weight are colourless, volatile liquids with pleasant odours, slightly soluble in water. Esters contain a carbonyl center, which gives rise to 120° C–C–O and O–C–O angles. Unlike amides, esters are structurally flexible functional groups because rotation about the C–O–C bonds has a low barrier. Their flexibility and low polarity is manifested in their physical properties; they tend to be less rigid (lower melting point) and more volatile (lower boiling point) than the corresponding amides. Quality Control of 3-Cyanophenylisocyanate

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Characterization of Aroma Compounds in Apple Cider Using Solvent-Assisted Flavor Evaporation and Headspace Solid-Phase Microextraction was written by Xu, Yan;Fan, Wenlai;Qian, Michael C.. And the article was included in Journal of Agricultural and Food Chemistry in 2007.Formula: C11H14O3 This article mentions the following:

The aroma-active compounds in 2 apple ciders were identified using gas chromatog.-olfactometry (GC-O) and GC-mass spectrometry (MS) techniques. The volatile compounds were extracted using solvent-assisted flavor evaporation (SAFE) and headspace solid-phase microextraction (HS-SPME). On the basis of odor intensity, the most important aroma compounds in the 2 apple cider samples were 2-phenylethanol, butanoic acid, octanoic acid, 2-methylbutanoic acid, 2-phenylethyl acetate, Et 2-methylbutanoate, Et butanoate, Et hexanoate, 4-ethylguaiacol, eugenol, and 4-vinylphenol. Sulfur-containing compounds, terpene derivatives, and lactones were also detected in ciders. Although most of the aroma compounds were common in both ciders, the aroma intensities were different. Comparison of extraction techniques showed that the SAFE technique had a higher recovery for acids and hydroxy-containing compounds, whereas the HS-SPME technique had a higher recovery for esters and highly volatile compounds In the experiment, the researchers used many compounds, for example, Ethyl 2-hydroxy-3-phenylpropanoate (cas: 15399-05-0Formula: C11H14O3).

Ethyl 2-hydroxy-3-phenylpropanoate (cas: 15399-05-0) belongs to esters. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Liquid esters of low volatility serve as softening agents for resins and plastics. Esters also include many industrially important polymers. Polymethyl methacrylate is a glass substitute sold under the names Lucite and Plexiglas; polyethylene terephthalate is used as a film (Mylar) and as textile fibres sold as Terylene, Fortrel, and Dacron.Formula: C11H14O3

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

5-Substituted 2-amino-4,6-dihydroxypyrimidines and 2-amino-4,6-dichloropyrimidines. Synthesis and inhibitory effects on immune-activated nitric oxide production was written by Jansa, Petr;Holy, Antonin;Dracinsky, Martin;Kolman, Viktor;Janeba, Zlatko;Kostecka, Petra;Kmonickova, Eva;Zidek, Zdenek. And the article was included in Medicinal Chemistry Research in 2014.Formula: C10H14O4 This article mentions the following:

A series of 5-substituted 2-amino-4,6-dihydroxypyrimidines were prepared by a modified condensation of the corresponding monosubstituted malonic acid diesters with guanidine in an excess of sodium ethoxide. The optimized procedure using Vilsmeier-Haack-Arnold reagent, followed by immediate deprotection of the (dimethylamino)methylene protecting groups, was developed to convert the 2-amino-4,6-dihydroxypyrimidine analogs to novel 5-substituted 2-amino-4,6-dichloropyrimidines in high yields. Pilot screening for biol. properties of the prepared compounds was done in mouse peritoneal cells using the in vitro nitric oxide (NO) assay. Irresp. of the substituent at the 5 position, 2-amino-4,6-dichloropyrimidines inhibited immune-activated NO production The most effective was 5-fluoro-2-amino-4,6-dichloropyrimidine with an IC₅₀ of 2 μM (higher activity than the most potent reference compound) while the IC₅₀s of other derivatives were within the range of 9-36 μM. The 2-amino-4,6-dihydroxypyrimidine counterparts were devoid of any NO-inhibitory activity. The compounds had no suppressive effects on the viability of cells. In the experiment, the researchers used many compounds, for example, Diethyl 2-(prop-2-yn-1-yl)malonate (cas: 17920-23-9Formula: C10H14O4).

Diethyl 2-(prop-2-yn-1-yl)malonate (cas: 17920-23-9) belongs to esters. Esters typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in essential oils and pheromones. Because of their lack of hydrogen-bond-donating ability, esters do not self-associate. Consequently, esters are more volatile than carboxylic acids of similar molecular weight.Formula: C10H14O4

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Parallel synthesis of isatin-based serine protease inhibitors was written by Shuttleworth, Stephen J.;Nasturica, Daniel;Gervais, Christian;Siddiqui, M. Arshad;Rando, Robert F.;Lee, Nola. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2000.Category: esters-buliding-blocks This article mentions the following:

The synthesis of N-functionalized isatins, such as I [R = CH(Me)COC₆H₄-3-OMe, R¹ = Me, R³ = H; R = CH₂CONH₂, CH₂COC₆H₄-4-Cl, R¹ = R³ = H], using parallel, solution synthesis is described. Functionalized polymers were employed as stoichiometric and catalytic reagents as well as purification media. The prepared isatins showed inhibition against a panel of serine proteases, i.e. human chymotrypsin, human leukocyte elastase, and human plasmin. In the experiment, the researchers used many compounds, for example, 3-Cyanophenylisocyanate (cas: 16413-26-6Category: esters-buliding-blocks).

3-Cyanophenylisocyanate (cas: 16413-26-6) belongs to esters. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Because of their lack of hydrogen-bond-donating ability, esters do not self-associate. Consequently, esters are more volatile than carboxylic acids of similar molecular weight.Category: esters-buliding-blocks

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthesis and biological evaluation of new MET inhibitors with 1,6-naphthyridinone scaffold was written by Wang, Ming-Shu;Zhuo, Lin-Sheng;Yang, Fan-Peng;Wang, Wen-Jie;Huang, Wei;Yang, Guang-Fu. And the article was included in European Journal of Medicinal Chemistry in 2020.Recommanded Product: Ethyl 2-(4-fluorophenyl)acetate This article mentions the following:

A potent and novel MET inhibitor, naphthyridin-4(1H)-one derivatives I and II [R¹ = Me, cyclopropyl, Bu, etc.; R² = H, Me, Et, 2-hydroxyethyl, 2-hydroxy-2-methylpropyl] was synthesized via a scaffold-hopping strategy of a 2,7-naphthyridinone MET kinase inhibitor III. Lead compound I had good potency (IC₅₀ of 9.8 nM), but unfavorable pharmacokinetic profiles (F = 12%, CL = 5.0 L/h/kg). Systematic structural optimization of compound I resulted in II [R¹ = cyclopropyl, R² = H] (MET, IC₅₀ = of 9.8 nM) with a comparable MET potency to that of compound IV and a favorable pharmacokinetic profile (F = 63%, CL = 0.12 L/h/kg). Further study of the derivatization of N(1) amine group of II [R¹ = cyclopropyl, R² = H] led to the discovery of compound II [R¹ = cyclopropyl, R² = Me] with good MET potency (IC₅₀ of 7.1 nM), promising VEGFR-2 selectivity (3226-fold) and a markedly drug-likeness improvement (F = 57.7%, CL = 0.02 L/h/kg). The excellent VEGFR-2 selectivity and favorable drug-likeness of II [R¹ = cyclopropyl, R² = Me] suggested that the 1,6-naphthyridine moiety could be used as a new scaffold for kinase inhibitor discovery. In the experiment, the researchers used many compounds, for example, Ethyl 2-(4-fluorophenyl)acetate (cas: 587-88-2Recommanded Product: Ethyl 2-(4-fluorophenyl)acetate).

Ethyl 2-(4-fluorophenyl)acetate (cas: 587-88-2) belongs to esters. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits. Acyl chlorides and acid anhydrides alcoholysis is another way to produce esters. Acyl chlorides and acid anhydrides react with alcohols to produce esters. Anydrous conditions are recommended since both acyl chlorides and acid anhydrides react with water.Recommanded Product: Ethyl 2-(4-fluorophenyl)acetate

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Volatile oils from Psidium guineense Swartz leaves: Chemical seasonality, antimicrobial, and larvicidal activities was written by Abrao, Fernando Yano;da Costa, Henrique Marques;Fiuza, Tatiana de Sousa;Ramada, Marcelo Henrique Soller;Santos, Adelair Helena dos;Romano, Camila Aline;da Cunha, Luiz Carlos;Neto, Jeronimo Raimundo de Oliveira;Borges, Leonardo Luiz;Ferreira, Heleno Dias;de Paula, Jose Realino. And the article was included in South African Journal of Botany in 2022.Safety of (E)-3,7-Dimethylocta-2,6-dien-1-yl acetate This article mentions the following:

Psidium guineense Swartz is a shrub used in urinary tract diseases, diarrhea, and dysentery. The aims of this study were to analyze the seasonal chem. variability of the volatile oils of P. guineense leaves for 12 mo, to evaluate the antimicrobial activity against bacteria and fungus, and the larvicidal activity against third-instar Aedes aegypti larvae. The identification of the volatile oil components was performed by gas chromatog. coupled with mass spectrometry (GC-MS). The antimicrobial and larvicidal activities were assessed by in vitro methodologies. The majority compounds of the volatile oil were (2Z,6E)-farnesol (15.1-51.2%), α-copaene (5.9-24.6%) and muurola-4,10(14)-dien-1β-ol (2.7-9.6%). The composition varied according to rainfall occurrence: Cluster I (volatile oils from leaves collected in Apr., June, July, August, Sept., Oct., and Dec.- low precipitation months), Cluster II (volatile oils from leaves collected in Jan., Feb., March, May, and Nov. – higher precipitation levels). Cluster I and Cluster II showed strong to moderate activity against Cryptococcus neoformans (MIC = 32-64μg/mL) and Micrococcus luteus (MIC = 16-32μg/mL) while promising larvicidal activity was observed against Ae. aegypti (LC50 20.5-36.4μg/mL; LC90 47.5-70.1μg/mL). This is the first report describing the seasonal variability of P. guineense volatile oils, antifungal activity against yeasts, and larvicidal activity over Ae. aegypti. In the experiment, the researchers used many compounds, for example, (E)-3,7-Dimethylocta-2,6-dien-1-yl acetate (cas: 105-87-3Safety of (E)-3,7-Dimethylocta-2,6-dien-1-yl acetate).

(E)-3,7-Dimethylocta-2,6-dien-1-yl acetate (cas: 105-87-3) belongs to esters. Esters are also usually derived from carboxylic acids. It may also be obtained by reaction of acid anhydride or acid halides with alcohols or by the reaction of salts of carboxylic acids with alkyl halides. Esterification is the general name for a chemical reaction in which two reactants (typically an alcohol and an acid) form an ester as the reaction product. Esters are common in organic chemistry and biological materials.Safety of (E)-3,7-Dimethylocta-2,6-dien-1-yl acetate

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Ruthenium Catalyzed Rearrangement of Ene-cyclopropenes. Divergent Reaction Pathways was written by Lopez-Rodriguez, Alberto;Dominguez, Gema;Perez-Castells, Javier. And the article was included in Journal of Organic Chemistry in 2019.HPLC of Formula: 17920-23-9 This article mentions the following:

The reaction of ene-cyclopropenes with Cp*RuCl(cod) leads to alkenyl bicyclo[3.1.0]hexanes, bicyclo[4.1.0]heptanes, and bicyclo[5.1.0]octanes. This reaction involves a reverse regioselectivity in the cyclopropene opening than with gold chlorides. With gem-disubstituted cyclopropenes, a novel cycloisomerization based on ring-opening nucleophilic attack and rearrangement is observed Alternatively, some gem-disubstituted cyclopropenes give dimerizations of the intermediate carbene. In the experiment, the researchers used many compounds, for example, Diethyl 2-(prop-2-yn-1-yl)malonate (cas: 17920-23-9HPLC of Formula: 17920-23-9).

Diethyl 2-(prop-2-yn-1-yl)malonate (cas: 17920-23-9) belongs to esters. Esters typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in essential oils and pheromones. Acyl chlorides and acid anhydrides alcoholysis is another way to produce esters. Acyl chlorides and acid anhydrides react with alcohols to produce esters. Anydrous conditions are recommended since both acyl chlorides and acid anhydrides react with water.HPLC of Formula: 17920-23-9

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Discrimination and Characterization of the Volatile Organic Compounds in Schizonepetae Spica from Six Regions of China Using HS-GC-IMS and HS-SPME-GC-MS was written by Li, Chao;Wan, Huiying;Wu, Xinlong;Yin, Jiaxin;Zhu, Limin;Chen, Hanjiang;Song, Xinbo;Han, Lifeng;Yang, Wenzhi;Yu, Heshui;Li, Zheng. And the article was included in Molecules in 2022.Application In Synthesis of Isopentyl 3-methylbutanoate This article mentions the following:

Volatile organic compounds (VOCs) are the main chem. components of Schizonepetae Spica (SS), which have pos. effects on the quality evaluation of SS. In this study, HS-SPME-GC-MS (headspace solid-phase microextraction-gas chromatog.-mass spectrometry) and HS-GC-IMS (headspace-gas chromatog.-ion mobility spectrometry) were performed to characterize the VOCs of SS from six different regions. A total of 82 VOCs were identified. In addition, this work compared the suitability of two instruments to distinguish SS from different habitats. The regional classification using orthogonal partial least squares discriminant anal. (OPLS-DA) shows that the HS-GC-IMS method can classify samples better than the HS-SPME-GC-MS. This study provided a reference method for identification of the SS from different origins. In the experiment, the researchers used many compounds, for example, Isopentyl 3-methylbutanoate (cas: 659-70-1Application In Synthesis of Isopentyl 3-methylbutanoate).

Isopentyl 3-methylbutanoate (cas: 659-70-1) belongs to esters. Esters are also usually derived from carboxylic acids. It may also be obtained by reaction of acid anhydride or acid halides with alcohols or by the reaction of salts of carboxylic acids with alkyl halides. Because of their lack of hydrogen-bond-donating ability, esters do not self-associate. Consequently, esters are more volatile than carboxylic acids of similar molecular weight.Application In Synthesis of Isopentyl 3-methylbutanoate

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Subtlety of the Structure-Affinity and Structure-Efficacy Relationships around a Nonpeptide Oxytocin Receptor Agonist was written by Frantz, Marie-Celine;Rodrigo, Jordi;Boudier, Laure;Durroux, Thierry;Mouillac, Bernard;Hibert, Marcel. And the article was included in Journal of Medicinal Chemistry in 2010.Category: esters-buliding-blocks This article mentions the following:

Very few nonpeptide oxytocin agonists have currently been reported, and none of them seem suitable for the in vivo investigation of the oxytocin mediated functions. In an attempt to rationalize the design of better tools, we have systematically studied the structural determinants of the affinity and efficacy of representative ligands of the V_1a, V₂, and OT receptor subtypes. Despite apparently obvious similarity between the ligand structures on one hand, and between the receptor subtypes on the other hand, the binding affinity and the functional activity profiles of truncated and hybrid ligands highlight the subtlety of ligand-receptor interactions for obtaining nonpeptide OT receptor agonists. In the experiment, the researchers used many compounds, for example, Methyl 4-fluoro-3-methylbenzoate (cas: 180636-50-4Category: esters-buliding-blocks).

Methyl 4-fluoro-3-methylbenzoate (cas: 180636-50-4) belongs to esters. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Esters are more polar than ethers but less polar than alcohols. They participate in hydrogen bonds as hydrogen-bond acceptors, but cannot act as hydrogen-bond donors, unlike their parent alcohols. This ability to participate in hydrogen bonding confers some water-solubility.Category: esters-buliding-blocks

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

The Search for Histamine H₄ Receptor Ligands with Anticancer Activity among Novel (Thio)urea Derivatives was written by Dominguez-Alvarez, Enrique;Lazewska, Dorota;Szabo, Zsanett;Hagenow, Stefanie;Reiner, David;Gajdacs, Mario;Spengler, Gabriella;Stark, Holger;Handzlik, Jadwiga;Kiec-Kononowicz, Katarzyna. And the article was included in ChemistrySelect in 2019.HPLC of Formula: 16413-26-6 This article mentions the following:

A series of (thio)urea-containing compounds I [R = Ph, Bn, 4-PhC₆H₄, etc.; X = O, S] and II [A = 1,4-phenylene, 1,3-xylylene, 4,4′-methylenebis(phenyl)] were initially designed and synthesized as potential ligands for the histamine H4 receptor (H4R). Considering the structural analogy of these thioureas to previously described seleno/thiourea compounds with anticancer and/or reversal multidrug resistance action in cancer cells, selected thioureas were evaluated in in-vitro cytotoxicity- and cancer multidrug resistance assays. The thiourea derivatives showed a good cytotoxic activity, being the compound II [R = 4-PhC₆H₄; X = S] the most active (IC₅₀ = 11.9 μM). They also enhanced the cytotoxicity of the topoisomerase inhibitors topotecan and doxorubicin in a checkerboard combination assay. Compound I [R = 4-PhC₆H₄; X = S] showed the strongest synergistic effect on topotecan activity, whereas I [R = 4-MeC₆H₄; X = S] was the best in combination with doxorubicin. These results could be a good starting point to design more potent and effective (thio)urea derivatives with anticancer activity. In the experiment, the researchers used many compounds, for example, 3-Cyanophenylisocyanate (cas: 16413-26-6HPLC of Formula: 16413-26-6).

3-Cyanophenylisocyanate (cas: 16413-26-6) belongs to esters. Volatile esters with characteristic odours are used in synthetic flavours, perfumes, and cosmetics. Certain volatile esters are used as solvents for lacquers, paints, and varnishes. Esters contain a carbonyl center, which gives rise to 120° C–C–O and O–C–O angles. Unlike amides, esters are structurally flexible functional groups because rotation about the C–O–C bonds has a low barrier. Their flexibility and low polarity is manifested in their physical properties; they tend to be less rigid (lower melting point) and more volatile (lower boiling point) than the corresponding amides. HPLC of Formula: 16413-26-6

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics