Category: esters-buliding-blocks

Synthesis and SAR studies of 5-(pyridin-4-yl)-1,3,4-thiadiazol-2-amine derivatives as potent inhibitors of Bloom helicase was written by Rosenthal, Andrew S.;Dexheimer, Thomas S.;Gileadi, Opher;Nguyen, Giang H.;Chu, Wai Kit;Hickson, Ian D.;Jadhav, Ajit;Simeonov, Anton;Maloney, David J.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2013.Recommanded Product: 3-Cyanophenylisocyanate This article mentions the following:

Human cells utilize a variety of complex DNA repair mechanisms to combat constant mutagenic and cytotoxic threats from both exogenous and endogenous sources. The RecQ family of DNA helicases, which includes Bloom helicase (BLM), plays an important function in DNA repair by unwinding complementary strands of duplex DNA and atypical DNA structures such as Holliday junctions. Mutations of the BLM gene can result in Bloom syndrome, an autosomal recessive disorder associated with cancer predisposition. BLM-deficient cells exhibit increased sensitivity to DNA damaging agents indicating that a selective BLM inhibitor could be useful in potentiating the anticancer activity of these agents. In this work, we describe the medicinal chem. optimization of the hit mol. following a quant. high-throughput screen of >355,000 compounds These efforts lead to the identification of ML216 and related analogs, which possess potent BLM inhibition and exhibit selectivity over related helicases. Moreover, these compounds demonstrated cellular activity by inducing sister chromatid exchanges, a hallmark of Bloom syndrome. In the experiment, the researchers used many compounds, for example, 3-Cyanophenylisocyanate (cas: 16413-26-6Recommanded Product: 3-Cyanophenylisocyanate).

3-Cyanophenylisocyanate (cas: 16413-26-6) 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, including apples, durians, pears, bananas, pineapples, and strawberries. 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.Recommanded Product: 3-Cyanophenylisocyanate

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

Mechanistic Evaluation of Bioorthogonal Decaging with trans-Cyclooctene: The Effect of Fluorine Substituents on Aryl Azide Reactivity and Decaging from the 1,2,3-Triazoline was written by Matikonda, Siddharth S.;Fairhall, Jessica M.;Fiedler, Franziska;Sanhajariya, Suchaya;Tucker, Robert A. J.;Hook, Sarah;Garden, Anna L.;Gamble, Allan B.. And the article was included in Bioconjugate Chemistry in 2018.Recommanded Product: Methyl 4-amino-2,5-difluorobenzoate This article mentions the following:

Bioorthogonal prodrug activation/decaging strategies need to be selective, rapid and release the drug from the masking group upon activation. The rates of the 1,3-dipolar cycloaddition between a trans-cyclooctene (TCO) and a series of fluorine-substituted azido-PABC self-immolative spacers caging two model drugs, and subsequent release from the 1,2,3-triazoline are reported. As the number of fluorine substituents on the PABC linker increases from one to four, the rate of cycloaddition increases by almost one order of magnitude. Using a combination of fluorescence, ¹H/¹⁹F NMR, and computational experiments, we have been able to determine how substituents on the PABC ring can influence the degradation rates and also the product distribution of the 1,2,3-triazoline. We have also been able to determine how these substituents influence the rate of imine hydrolysis and 1,6-self-immolation decaging rates of the generated anilines. The NMR and computational studies demonstrate that fluorine substituents on the aromatic ring lower the transition state energy required for converting the triazoline to the imine or aziridine intermediates via extrusion of diat. nitrogen, and that in the case of a tetrafluoro substituted aromatic ring, it is the imine hydrolysis and 1,6-self-immolation that is rate-limiting. This knowledge further enhances the understanding of factors which influence the stability of triazolines, and enables potential applications of fluorinated aromatics, in particular, perfluorinated aromatics, in synthetic chem. and sustained-release drug delivery systems. In the experiment, the researchers used many compounds, for example, Methyl 4-amino-2,5-difluorobenzoate (cas: 952285-52-8Recommanded Product: Methyl 4-amino-2,5-difluorobenzoate).

Methyl 4-amino-2,5-difluorobenzoate (cas: 952285-52-8) 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. 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: Methyl 4-amino-2,5-difluorobenzoate

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

Synthesis of podophyllotoxin-glycosyl triazoles via click protocol mediated by silver (I)-N-heterocyclic carbenes and their anticancer evaluation as topoisomerase-II inhibitors was written by Nerella, Srinivas;Kankala, Shravankumar;Gavaji, Brahmeshwari. And the article was included in Natural Product Research in 2021.Product Details of 4163-60-4 This article mentions the following:

Herein we report the regioselective synthesis of podophyllotoxin-Glycosyl triazole hybrids catalyzed by Ag(I)-N-heterocyclic carbene (Ag(I)-NHC) in a short reaction time (∼30 min) at ambient conditions. In principle, it is the first report of Click alkyne-azide cycloaddition catalyzed by Ag(I)-NHC catalyst and moreover, this new methodol. yielded good results when compared with traditional CuAAC in terms of reaction time and selectivity. The synthesized compounds were further explored for in vitro anticancer activity against four human cancer cell lines Du145, HeLa, A-549, and MCF-7 and found that these synthesized compounds possess significant anticancer activity. Further, the compounds and were identified as promising leads due to their better activity across all cell lines than that of the standard drug etoposide. Mol. docking studies of I & II with DNA Topoisomerase-II were revealed that the free energy calculations of active compounds were in good agreement with observed IC₅₀ values. In the experiment, the researchers used many compounds, for example, (2S,3R,4S,5S,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 4163-60-4Product Details of 4163-60-4).

(2S,3R,4S,5S,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 4163-60-4) 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. 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.Product Details of 4163-60-4

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

Design and Synthesis of Nonpeptide Inhibitors of Hepatocyte Growth Factor Activation was written by Venukadasula, Phanindra K. M.;Owusu, Benjamin Y.;Bansal, Namita;Ross, Larry J.;Hobrath, Judith V.;Bao, Donghui;Truss, Jackie W.;Stackhouse, Murray;Messick, Troy E.;Klampfer, Lidija;Galemmo, Robert A.. And the article was included in ACS Medicinal Chemistry Letters in 2016.Application In Synthesis of 3-Cyanophenylisocyanate This article mentions the following:

In this letter the authors report first nonpeptide inhibitors of hepatocyte growth factor (HGF) activation. These compounds inhibit the three proteases (matriptase, hepsin, and HGF activator) required for HGF maturation. The authors show that several compounds I [Z = Me, HO, HOCH₂, MeOCH₂] block activation of fibroblast-derived pro-HGF, thus preventing fibroblast-induced scattering of DU145 prostate cancer cells. One of these compounds (SRI 31215) I [Z = Me] is very soluble (91 μM) and has excellent microsome stability (human t_1/2 = 162 min; mouse t_1/2 = 296 min). In mouse I [Z = Me] has an in vivo t_1/2 = 5.8 h following IV administration. The high solubility of I [Z = Me] and IV t_1/2 make this compound a suitable prototype “triplex inhibitor” for the study of the inhibition of HGF activation in vivo. In the experiment, the researchers used many compounds, for example, 3-Cyanophenylisocyanate (cas: 16413-26-6Application In Synthesis of 3-Cyanophenylisocyanate).

3-Cyanophenylisocyanate (cas: 16413-26-6) 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. 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.Application In Synthesis of 3-Cyanophenylisocyanate

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

Discovery of a 1-Methyl-3,4-dihydronaphthalene-Based Sphingosine-1-Phosphate (S1P) Receptor Agonist Ceralifimod (ONO-4641). A S1P₁ and S1P₅ Selective Agonist for the Treatment of Autoimmune Diseases was written by Kurata, Haruto;Kusumi, Kensuke;Otsuki, Kazuhiro;Suzuki, Ryo;Kurono, Masakuni;Komiya, Takaki;Hagiya, Hiroshi;Mizuno, Hirotaka;Shioya, Hiroki;Ono, Takeji;Takada, Yuka;Maeda, Tatsuo;Matsunaga, Norikazu;Kondo, Tetsu;Tominaga, Sachiko;Nunoya, Ken-ici;Kiyoshi, Hidekazu;Komeno, Masaharu;Nakade, Shinji;Habashita, Hiromu. And the article was included in Journal of Medicinal Chemistry in 2017.Category: esters-buliding-blocks This article mentions the following:

The discovery of 1-({6-[(2-methoxy-4-propylbenzyl)oxy]-1-methyl-3,4-dihydronaphthalen-2-yl}methyl)azetidine3-carboxylic acid (I) (13n, ceralifimod, ONO-4641), a sphingosine-1-phosphate (S1P) receptor agonist selective for S1P₁ and S1P₅, is described. While it has been revealed that the modulation of the S1P₁ receptor is an effective way to treat autoimmune diseases such as relapsing-remitting multiple sclerosis (RRMS), it was also reported that activation of the S1P₃ receptor is implicated in some undesirable effects. The authors carried out a structure-activity relationship (SAR) study of hit compound 6 with an amino acid moiety in the hydrophilic head region. Following identification of a lead compound with a dihydronaphthalene central core by inducing conformational constraint, optimization of the lipophilic tail region led to the discovery of I as a clin. candidate that exhibited >30 000-fold selectivity for S1P₁ over S1P₃ and was potent in a peripheral lymphocyte lowering (PLL) test in mice (ED₅₀ = 0.029 mg/kg, 24 h after oral dosing). In the experiment, the researchers used many compounds, for example, Methyl 2-methoxy-4-methylbenzoate (cas: 81245-24-1Category: esters-buliding-blocks).

Methyl 2-methoxy-4-methylbenzoate (cas: 81245-24-1) belongs to esters. Carboxylic acid esters of low molecular weight are colourless, volatile liquids with pleasant odours, slightly soluble in water. 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

A Method for Obtaining Defined End Groups of Polymethacrylates Prepared by the RAFT Process during Aminolysis was written by Roth, Peter J.;Kessler, Daniel;Zentel, Rudolf;Theato, Patrick. And the article was included in Macromolecules (Washington, DC, United States) in 2008.Quality Control of Benzyl benzodithioate This article mentions the following:

We presented a simple modification of the aminolysis of polymethacrylates prepared by the RAFT process overcoming the problems of thiolactone and side product formation. The method uses the high reactivity of Me methanethiosulfonate toward thiols, thus favoring Me disulfide formation even in the presence of oxygen. The transformed disulfide end group showed a higher affinity toward a gold surface than the dithioester end group and could successfully be employed for encapsulation of gold nanoparticles. This method enables polymethacrylates to be grafted onto metal surfaces and also opens new routes to end-group functionalization of RAFT polymers. In the experiment, the researchers used many compounds, for example, Benzyl benzodithioate (cas: 27249-90-7Quality Control of Benzyl benzodithioate).

Benzyl benzodithioate (cas: 27249-90-7) 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. 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.Quality Control of Benzyl benzodithioate

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

Temperature Driven Self-Assembly of a Zwitterionic Block Copolymer That Exhibits Triple Thermoresponsivity and pH Sensitivity was written by Jimenez, Zulma A.;Yoshida, Ryo. And the article was included in Macromolecules (Washington, DC, United States) in 2015.Synthetic Route of C14H12S2 This article mentions the following:

We report a zwitterionic block copolymer composed of N-isopropylacrylamide and N,N-dimethyl-N-(3-(methacrylamido)propyl)ammoniopropanesulfonate monomers which self-assembles into different structures depending on the solution temperature As the temperature is increased from 20 to 70 °C, the solubility of the polymer switches direction from insoluble to soluble to insoluble to soluble During this process, the polymer self-assembly changes from polymersomes to micelles. These extraordinary transitions are possible because of the hydrophilic-hydrophobic ratio of the polymer blocks and the presence of a carboxyl end group attached to the end of the poly(N-isopropylacrylamide) chain. Addnl., one of these transitions can be controlled by the pH of the solution thanks to the protonation-deprotonation of the carbonyl and the charge neutralization of the ammonium moieties. The present work opens the possibility of designing polymers with temperature driven self-assembly properties that could be used for biomedical applications. In the experiment, the researchers used many compounds, for example, Benzyl benzodithioate (cas: 27249-90-7Synthetic Route of C14H12S2).

Benzyl benzodithioate (cas: 27249-90-7) 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. Many esters have the potential for conformational isomerism, but they tend to adopt an s-cis (or Z) conformation rather than the s-trans (or E) alternative, due to a combination of hyperconjugation and dipole minimization effects. The preference for the Z conformation is influenced by the nature of the substituents and solvent, if present. Lactones with small rings are restricted to the s-trans (i.e. E) conformation due to their cyclic structure.Synthetic Route of C14H12S2

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

Biotransformation of phenolic profiles and improvement of antioxidant capacities in jujube juice by select lactic acid bacteria was written by Li, Tianlin;Jiang, Tian;Liu, Ning;Wu, Caiyun;Xu, Huaide;Lei, Hongjie. And the article was included in Food Chemistry in 2021.Formula: C6H10O2 This article mentions the following:

The objective of this study was to investigate the effects of four com. lactic acid bacteria (LAB), namely L. acidophilus, L. casei, L. helveticus and L. plantarum, on the phenolic profiles, antioxidant capacities and flavor profiles of jujube juices prepared from two crop varieties (Ziziphus Jujuba cv. Muzao and Hetian). Results showed that both jujube juices were excellent matrixes for LAB growth with more than 11 log CFU/mL of viable counts at the end of fermentation LAB fermentation dramatically increased total phenolic content, while decreased total flavonoid content of jujube juices. However, antioxidant capacities based on DPPH and FRAP methods were significantly improved by LAB fermentation and pos. correlated with caffeic acid and rutin contents. Furthermore, a total of 74 volatile compounds were identified and increased in total content by LAB fermentation, which resulted in 22 and 19 new flavor volatiles formation in Muzao juice and Hetian juice, resp. In the experiment, the researchers used many compounds, for example, 5-Ethyldihydrofuran-2(3H)-one (cas: 695-06-7Formula: C6H10O2).

5-Ethyldihydrofuran-2(3H)-one (cas: 695-06-7) 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. Formula: C6H10O2

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

Nucleophilic fluorination of β-ketoester derivatives with HBF₄ was written by Pasceri, Raffaele;Bartrum, Hannah E.;Hayes, Christopher J.;Moody, Christopher J.. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2012.Name: Ethyl 3-oxo-3-(thiophen-2-yl)propanoate This article mentions the following:

Treating readily available α-diazo-β-keto esters with HBF₄ results in nucleophilic fluorination by the usually inert and stable tetrafluoroborate anion. The resulting α-fluoro-β-ketoesters are highly versatile synthetic intermediates, for example in the preparation of fluoro-heterocycles, as illustrated by the direct formation of fluoro-pyrimidines, -pyrazoles and -coumarins in a single step. In the experiment, the researchers used many compounds, for example, Ethyl 3-oxo-3-(thiophen-2-yl)propanoate (cas: 13669-10-8Name: Ethyl 3-oxo-3-(thiophen-2-yl)propanoate).

Ethyl 3-oxo-3-(thiophen-2-yl)propanoate (cas: 13669-10-8) 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. 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.Name: Ethyl 3-oxo-3-(thiophen-2-yl)propanoate

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

The Willgerodt reaction with 2-acetylthiophene was written by Dann, Otto;Distler, Harry. And the article was included in Chemische Berichte in 1951.Recommanded Product: 19432-68-9 This article mentions the following:

Because the addition of RCH₂CONH₂ (I) (R = S.CH:CH.CH:C throughout the abstract) to the nutrient in the biosynthesis of penicillia gave a product with a highly increased activity and 2-thienylmethylpenicillin showed indications of permanent action, a synthesis of I by the Willgerodt reaction is carried out. Heating 10 g. RCOMe, 18 cc. dioxane, 22 cc. concentrated NH₄OH, 15 g. S, and 12 cc. yellow (NH₄)₂S_x in a bomb within 1 hr. at 142°, keeping the mixture 3.25 hrs. at 142°, raising the temperature the last 1/4 hr. to 152°, evaporating the contents of 3 runs on the water bath, and extracting the residue with hot H₂O gives 68% I, m. 146.5°. Refluxing 700 mg. I in 15 cc. 10% KOH 12 hrs. and acidifying with concentrated HCl give 300 mg. RCH₂CO₂H (II), m. 64°. Refluxing 6 g. II with 30 g. MeOH and 1 g. concentrated HCl 5 hrs. gives 82% RCH₂CO₂Me, b₂₅ 119-22°, n_D^19.5 1.5243. Adding dropwise 86 g. SnCl₄ over a period of 2 hrs. to 37.3 g. 2,5-dimethylthiophene, 26 g. AcCl, and 400 g. C₆H₆ with ice-NaCl cooling and stirring, and stirring the mixture 3 hrs. at 25-30° give 91% (with AlCl₃ in CS₂, 60%) 2,5-dimethyl-3-acetylthiophene (III), b₈ 96-105°, n_D²⁴ 1.5404 (semicarbazone, m. 211°). Refluxing 4.5 hrs. 132 g. III, 120 g. morpholine, and 45 g. S, pouring the mixture into 100 cc. EtOH-Me₂CO (1:1), and cooling with ice-NaCl give 56.8% 3-(2,5-dimethylthienyl)thioacetomorpholide (IV), shiny slightly yellow leaflets, m. 76°. Refluxing 12 hrs. 124 g. IV with 120 g. KOH in 1.2 l. MeOH, evaporating the mixture on a water bath to dryness, dissolving the residue in 700 cc. hot H₂O, washing the solution with CS₂ and ether, and acidifying with dilute H₂SO₄ give 50% 3-(2,5-dimethylthienyl)acetic acid, b_2.6 152-3°. In the experiment, the researchers used many compounds, for example, Methyl 2-thienylacetate (cas: 19432-68-9Recommanded Product: 19432-68-9).

Methyl 2-thienylacetate (cas: 19432-68-9) 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, including apples, durians, pears, bananas, pineapples, and strawberries. 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: 19432-68-9

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