Category: esters-buliding-blocks

Oligosaccharide-camptothecin conjugates as potential antineoplastic drugs: Design, synthesis and biological evaluation was written by Li, Maolin;Ye, Wenchong;Fu, Kaishuo;Cui, zhou;Shi, Yonghui;Huang, Weiping;Chen, Wenming;Hu, Jiliang;Jiang, Zhilin;Zhou, Wen. And the article was included in European Journal of Medicinal Chemistry in 2020.Safety of (2S,3R,4S,5S,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate This article mentions the following:

Thirty novel 20 (S)-O-linked camptothecin (CPT) glycoconjugates were synthesized. They showed more potent in vitro cytotoxicities over irinotecan, but very weak direct topoisomerase I (Topo I) inhibition was observed at 100.0μM. Oligosaccharide types, length of a PEG linker and acetyl groups exerted obvious effects on cytotoxicity, selectivity, water solubility and stability of the newly synthesized CPT glycoconjugates. Construct 40, with a bleomycin (BLM) disaccharide linked to diethylene glycol in the introduced ester moiety, demonstrated a superior antitumor activity and a distinct selectivity compared to CPT. No toxicity was detectable in animal acute toxicity i.v. (160 mg/kg). Collectively, attachment of oligosaccharides with tumor targeting to 20 (S)-OH of CPT could offer a solution to the daunting problems posed by current Topo I poisons. 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: 4163-60-4Safety of (2S,3R,4S,5S,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate).

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

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

Associations between phthalic acid esters in household dust and childhood asthma in Shanghai, China was written by Zhang, Jialing;Sun, Chanjuan;Lu, Rongchun;Zou, Zhijun;Liu, Wei;Huang, Chen. And the article was included in Environmental Research in 2021.Reference of 84-61-7 This article mentions the following:

Phthalic acid esters (PAEs) have a neg. impact on human health and are widely distributed in China. As part of the China, Children, Home, Health (CCHH) study, we investigated the associations between childhood asthmatic symptoms and PAEs in settled house dust in Shanghai, China. We found that di-2-ethylhexyl phthalate (DEHP), di-Bu phthalate (DBP), and diisobutyl phthalate (DiBP) were abundant in the indoor environment. A total of 27% of children suffered from diagnosed asthma. The Mann-Whitney U test and multiple logistic regression were used to obtain the associations between PAEs and childhood asthmatic symptoms. Stratification anal. was performed to reveal the influence of gender on the associations between PAE exposure and target symptoms. Compared with low concentrations of PAEs, high concentrations of high mol. weight PAEs (HMW-PAEs) were significantly associated with childhood diagnosed asthma (adjusted odds ratios (AORs) > 1, P < 0.05). Moreover, significantly neg. associations were found between high concentrations of DiBP and current cough (AORs<1, P < 0.05). All significantly pos. associations were observed among girls, and most of the associations of di-Me phthalate (DMP) and di-Et phthalate (DEP) exposure with the studied symptoms among girls were higher than those among boys. Exposure to PAEs may be a risk factor for asthmatic symptoms in children, especially in girls. In the experiment, the researchers used many compounds, for example, Dicyclohexyl phthalate (cas: 84-61-7Reference of 84-61-7).

Dicyclohexyl phthalate (cas: 84-61-7) 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. Cyclic esters are called lactones, regardless of whether they are derived from an organic or inorganic acid. One example of an organic lactone is γ-valerolactone.Reference of 84-61-7

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

Synthesis and pharmacological properties of ureidomethylcarbamoylphenylketone derivatives. A new potent and subtype-selective nonpeptide CCK-B/gastrin receptor antagonist, S-0509 was written by Hagishita, Sanji;Murakami, Yosushi;Seno, Kaoru;Kamata, Susumu;Haga, Nobuhiro;Konoike, Toshiro;Kanda, Yasuhiko;Kiyama, Ryuichi;Shiota, Takeshi;Ishihara, Yasunobu;Ishikawa, Michio;Shimamura, Mayumi;Abe, Koji;Yoshimura, Koji. And the article was included in Bioorganic & Medicinal Chemistry in 1997.Recommanded Product: 16413-26-6 This article mentions the following:

A novel series of CCK-B/gastrin receptor antagonists-ureidomethylcarbamoylphenylketone derivatives-were designed, synthesized, and evaluated for activity. Structure-activity relationship studies revealed the importance of a carboxylic acid at substituent R₂ and a tert-butoxycarbonyl group at R₁ in structure A. Ureidomethylcarbamoylphenylketone PhCO-2-C₆H₄N(CH₂CO₂CMe₃)COCH₂NHCONHC₆H₄-3-CO₂H (I) (S-0509) showed remarkable affinity for the CCK-B/gastrin receptor and a subtype selectivity profile in vitro. Administration (id) of I led to excellent inhibition of gastric acid secretion induced by pentagastrin in anesthetized rats with an ED₅₀ value of 0.014 mg/kg. Furthermore, I proved to have poor blood-brain permeability by its small effect on enhancement of morphine analgesia. Thus, I has an increase in selectivity for the peripheral effects of gastrin antagonism from the central effects of CCK-B antagonism. In the experiment, the researchers used many compounds, for example, 3-Cyanophenylisocyanate (cas: 16413-26-6Recommanded Product: 16413-26-6).

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. 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.Recommanded Product: 16413-26-6

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

Synthesis, carbonic anhydrase II/IX/XII inhibition, DFT, and molecular docking studies of hydrazide-sulfonamide hybrids of 4-methylsalicyl- and acyl-substituted hydrazide was written by Khushal, Adil;Mumtaz, Amara;Shadoul, Wamda Ahmed;Zaidi, Syeda Huda Mehdi;Rafique, Hummera;Munir, Abida;Maalik, Aneela;Shah, Syed Jawad Ali;Baig, Ayesha;Khawaja, Wajiha;Al-Rashida, Mariya;Hashmi, Muhammad Ali;Iqbal, Jamshed. And the article was included in BioMed Research International in 2022.Reference of 81245-24-1 This article mentions the following:

Synthesis of hydrazide-sulfonamide hybrids I [R = 4-Me, 3-MeO, 2-MeO-4-Me, 2-HO-4-Me, R¹ = 4-MeC₆H₄, 4-MeOC₆H₄, 4-O₂NC₆H₄, 4-BrC₆H₄, 2-naphthyl, n = 0, 1] was carried out by the reaction of aryl and acyl hydrazides with substituted sulfonyl chlorides. Final product formation was confirmed by FT-IR, NMR, and EI-MS. D. functional theory (DFT) calculations were performed on all the synthesized compounds to get the ground-state geometries and compute NMR properties. NMR computations were in excellent agreement with the exptl. NMR data. All the synthesized hydrazide-sulfonamide hybrids I were evaluated in vitro against CA II, CA IX, and CA XII isoenzymes for their carbonic anhydrase inhibition activities. Among the entire series, only compounds I [R = 2-MeO-4-Me, R¹ = 4-MeC₆H₄, n = 0; R = 3-MeO, R¹ = 4-O₂NC₆H₄, 2-naphthyl, n = 1] were highly selective inhibitors of hCA IX and did not inhibit hCA XII. To investigate the binding affinity of these compounds, mol. docking studies of compounds I [R = 3-MeO, R¹ = 4-O₂NC₆H₄, 2-naphthyl, n = 1] were carried out against both hCA IX and hCA XII. By using BioSolveIT’s SeeSAR software, further studies to provide visual clues to binding affinity indicate that the structural elements that were responsible for this were also studied. The binding of these compounds with hCA IX was highly favorable (as expected) and in agreement with the exptl. data. In the experiment, the researchers used many compounds, for example, Methyl 2-methoxy-4-methylbenzoate (cas: 81245-24-1Reference of 81245-24-1).

Methyl 2-methoxy-4-methylbenzoate (cas: 81245-24-1) 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 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. Reference of 81245-24-1

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

Pd-Catalyzed Divergent C(sp²)-H Activation/Cycloimidoylation of 2-Isocyano-2,3-diarylpropanoates was written by Tang, Shi;Yang, Sheng-Wen;Sun, Hongwei;Zhou, Yali;Li, Juan;Zhu, Qiang. And the article was included in Organic Letters in 2018.Quality Control of Ethyl 2-fluorophenylacetate This article mentions the following:

A Pd-catalyzed site-selective C(sp²)-H activation/cycloimidoylation of 2-isocyano-2,3-diarylpropanoates to construct diverse cyclic imine products has been developed. Six-membered 3,4-dihydroisoquinolines containing a C3 quaternary carbon center were generated dominantly by using bulky Ad₂Pn-Bu as a ligand, while five-membered 1,1-disubstituted 1H-isoindoles were formed preferentially in the presence of bidentate phosphine ligand DPPB. The selectivity for 1H-isoindole formation was enhanced by using steric hindered aryl iodides. DFT calculations suggested that the exptl. observed ligand-controlled selectivity was a result of trans effect. In the experiment, the researchers used many compounds, for example, Ethyl 2-fluorophenylacetate (cas: 584-74-7Quality Control of Ethyl 2-fluorophenylacetate).

Ethyl 2-fluorophenylacetate (cas: 584-74-7) 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. 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.Quality Control of Ethyl 2-fluorophenylacetate

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

Sugar-Oligoamides: Synthesis of DNA Minor Groove Binders was written by Badia, Concepcion;Souard, Florence;Vicent, Cristina. And the article was included in Journal of Organic Chemistry in 2012.Quality Control of Ethyl 4-nitro-1H-pyrrole-2-carboxylate This article mentions the following:

Sugar-oligoamides, e.g. I, have been designed and synthesized as structurally simple carbohydrate-based ligands to study carbohydrate-minor groove DNA interactions. Here we report an efficient solution-phase synthetic strategy to obtain two broad families of sugar-oligoamides. The first type, structure vector A (-Py[Me]-γ-Py-Ind), has a Me group present as a substituent on the nitrogen of pyrrole B, connected to the C terminal of the oligoamide fragment. The second type, structure vector B (-Py[(CH₂)₁₁OH]-γ-Py-Ind), has an alkyl chain present on the nitrogen of pyrrole B connected to the C terminal of the oligoamide fragment and has been designed to access to di- and multivalent sugar-oligoamides. By using sequential DIPC/HOBt coupling reactions, the oligoamide fragment -Py[R]-γ-Py-Ind has been constructed. The last coupling reaction between the anomeric amino sugar and the oligoamide fragment was carried out by activating the acid derivative as a BtO- ester, which has been performed by using TFFH. The isolated esters (BtO-Py[R]-γ-Py-Ind) were coupled with selected amino sugars using DIEA in DMF. The synthesis of two different selective model vectors (vector A and vector B) and two types of water-soluble sugar-oligoamide ligands, with vector A structure, e.g. I, and with vector B structure, was carried out. In the experiment, the researchers used many compounds, for example, Ethyl 4-nitro-1H-pyrrole-2-carboxylate (cas: 5930-92-7Quality Control of Ethyl 4-nitro-1H-pyrrole-2-carboxylate).

Ethyl 4-nitro-1H-pyrrole-2-carboxylate (cas: 5930-92-7) 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.Quality Control of Ethyl 4-nitro-1H-pyrrole-2-carboxylate

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

Quantitative analysis of characteristic aromatic compounds in red berry (Myrica rubra Sieb. Et Zucc) by HS-SPME and GC/MS was written by Kang, Wenhuai;Xu, Yan;Fan, Wenlai;Jiang, Wenguang;Zhou, Zengqun;Zhu, Yongfeng. And the article was included in Shipin Gongye Keji in 2009.Related Products of 1190-39-2 This article mentions the following:

Red bayberry (Myrica rubra Sieb. et Zucc) was a subtropical fruit tree native to China Southern, and its mature berry was characterized by strong aromatic flavor. The investigation on flavor was very significant. In this research, the volatile characteristic flavor was investigated using the liquid-liquid extraction (LLE) and headspace-solid phase microextraction (HS-SPME) technique, and the gas chromatog. mass spectrometry (GC/MS). The results showed that there were 60 components identified by HS-SPME-GC/MS. The primary classification of volatile components was terpenoids (40%). The second category was alcs. (22%). The contents of acid and ester were lower, with 1% and 3% resp. It showed that the content of β-caryophyllene was highest (1069.8 μg/L) among them. The research on anal. of red bayberry characteristic flavor was significant theor. basis for improving construction of the quality evaluation system and for investigating effect of the deep processing technol. on the flavor. In the experiment, the researchers used many compounds, for example, malonic acid dibutyl ester (cas: 1190-39-2Related Products of 1190-39-2).

malonic acid dibutyl ester (cas: 1190-39-2) 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. 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. Related Products of 1190-39-2

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

Non-Saccharomyces yeasts highly contribute to characterisation of flavor profiles in greengage fermentation was written by Qiu, Shuang;Chen, Kai;Liu, Chang;Wang, Yingxiang;Chen, Tao;Yan, Guoliang;Li, Jingming. And the article was included in Food Research International in 2022.Reference of 118-61-6 This article mentions the following:

Non-Saccharomyces yeasts play an important role in greengage fermentation To obtain practical non-Saccharomyces yeasts for high-acid fermentation environments, and improve the flavor quality of fermented greengage beverage, four indigenous acid-tolerant non-Saccharomyces yeast strains were used to conduct greengage fermentation Hanseniaspora occidentalis, Pichia terricola, and Issatchenkia orientalis were competitively fermentable and significantly decreased the concentration of citric acid and malic acid. HS-SPME and GC-MS were used to analyze the aroma profiles, and results showed that H. occidentalis has potential to produce explicit fruity aroma, since the fermented beverages obtained more esters. Moreover, phenolic acids had the highest concentration among polyphenols of fermented greengage beverage. Comparatively, spontaneous fermentation produced higher levels of most polyphenols, whereas P. terricola treatment resulted predominantly in partial phenolic acids. Kendall coefficients indicated that procyanidins and glycosidic bound flavonols significantly pos. correlated with more than 30% volatiles. This study verified the biofunctions of non-Saccharomyces yeasts and applied their potential for flavor improvement in the production of high-acidity fermented fruit beverages. In the experiment, the researchers used many compounds, for example, Ethyl 2-hydroxybenzoate (cas: 118-61-6Reference of 118-61-6).

Ethyl 2-hydroxybenzoate (cas: 118-61-6) 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. 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. Reference of 118-61-6

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

Volatile profile of elderberry juice: Effect of lactic acid fermentation using L. plantarum, L. rhamnosus and L. casei strains was written by Ricci, Annalisa;Cirlini, Martina;Levante, Alessia;Dall’Asta, Chiara;Galaverna, Gianni;Lazzi, Camilla. And the article was included in Food Research International in 2018.HPLC of Formula: 659-70-1 This article mentions the following:

In this study we explored, for the first time, the lactic acid fermentation of elderberry juice (EJ). A total of 15 strains isolated from dairy and plant matrixes, belonging to L. plantarum, L. rhamnosus and L. casei, were used for fermentations The volatile profile of started and unstarted EJ was characterized by HS-SPME/GC-MS technique after 48 h of fermentation and 12 days of storage at 4 °C. All L. plantarum and L. rhamnosus strains exhibited a good capacity of growth while not all L. casei strains showed the same ability. The aromatic profile of fermented juices was characterized by the presence of 82 volatile compounds pertaining to different classes: alcs., terpenes and norisoprenoids, organic acids, ketones and esters. Elderberry juice fermented with L. plantarum strains showed an increase of total volatile compounds after 48 h while the juices fermented with L. rhamnosus and L. casei exhibited a larger increase after the storage. The highest concentration of total volatile compounds were observed in EJ fermented with L. plantarum 285 isolated from dairy product. Ketones increased in all fermented juices both after fermentation and storage and the most concentrated were acetoin and diacetyl. The organic acids were also affected by lactic acid fermentation and the most abundant acids detected in fermented juices were acetic acid and isovaleric acid. Hexanol, 3-hexen-1-ol (Z) and 2-hexen-1-ol (E) were pos. influenced during dairy lactic acid bacteria strains fermentation The most represented esters were Et acetate, Me isovalerate, isoamyl isovalerate and Me salicylate, all correlated with fruit notes. Among terpenes and norisoprenoids, β-damascenone resulted the main representative with its typical note of elderberry. Furthermore, coupling obtained data with multivariate statistical analyses, as Principal Component Anal. (PCA) and Classification Trees (CT), it was possible to relate the characteristic volatile profile of samples with the different species and strains applied in this study. In the experiment, the researchers used many compounds, for example, Isopentyl 3-methylbutanoate (cas: 659-70-1HPLC of Formula: 659-70-1).

Isopentyl 3-methylbutanoate (cas: 659-70-1) 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. 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.HPLC of Formula: 659-70-1

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

Search for new pharmacophores for antimalarial activity. Part I: Synthesis and antimalarial activity of new 2-methyl-6-ureido-4-quinolinamides was written by Madapa, S.;Tusi, Z.;Sridhar, D.;Kumar, A.;Siddiqi, M. I.;Srivastava, K.;Rizvi, A.;Tripathi, R.;Puri, S. K.;Shiva Keshava, G. B.;Shukla, P. K.;Batra, S.. And the article was included in Bioorganic & Medicinal Chemistry in 2009.Product Details of 16413-26-6 This article mentions the following:

A total of 80 new 2-methyl-6-ureido-4-quinolinamides were synthesized and evaluated for their antimalarial activity. Several analogs elicited the antimalarial effect at MIC of 0.25 mg/mL against the chlooquine-sensitive P. falciparum strain. The IC₅₀ values of the active compounds were observed to be in ng/mL range and two of the analogs have better IC₅₀ value than the standard chloroquine. In the in vivo assay against mdr CQ resistant P. yoelii N67/P. yoelii nigeriensis, however, none of the compound showed complete suppression of parasitemia on day 7. One of the compounds displayed significant antibacterial effect against several strains of bacteria and was many-fold better than the standard drug gentamicin. In the experiment, the researchers used many compounds, for example, 3-Cyanophenylisocyanate (cas: 16413-26-6Product Details of 16413-26-6).

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. 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.Product Details of 16413-26-6

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