Category: 924-99-2

Ziao, Nahosse published the artcileAmino nitrogen and carbonyl oxygen in competitive situations: which is the best hydrogen-bond acceptor site?, Product Details of C7H13NO2, the publication is CrystEngComm (2002), 326-335, database is CAplus.

The relative H-bond acceptor abilities of amino N and carbonyl O in various chem. environments were studied using data retrieved from the Cambridge Structural Database (CSD) and via ab initio MO calculations Surveys of the CSD for H bonds between HX (X = N, O) donors and push-pull or saturated amino ketone and amino ester mol. fragments show that the H bonds are much more frequent on the O than on the amino N. In the push-pull families, the H-bonding (HB) ability of the carbonyl O is increased by conjugation between the lone pair of the amino substituent and the C=O group, a behavior similar to resonance-assisted H bonding. The unexpected behavior of twisted amides, in which only the amino N is involved in H bonding, is pointed out. This unusual feature is explained by the disruption of conjugation between the amino lone pair and the carbonyl owing to the cyclization involving the amino moiety. In aliphatic systems, the amino N retains its HB ability but is still involved in a rather low number of contacts. This behavior reflects the sensitivity of the amino N to steric hindrance. The relative strengths of the H bonds on the carbonyl O in ketones and esters follow the exptl. order of H-bond basicity as observed in solution through the pK_HB scale. Ab initio MO calculations (B3LYP/6-31+G^** level) of electrostatic and charge transfer descriptors also confirm the exptl. observations. pK_a.

CrystEngComm published new progress about 924-99-2. 924-99-2 belongs to esters-buliding-blocks, auxiliary class Alkenyl,Amine,Aliphatic hydrocarbon chain,Ester, name is Ethyl 3-(dimethylamino)acrylate, and the molecular formula is C16H24BF4Ir, Product Details of C7H13NO2.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Mathiyazhagan, Kasinathan published the artcileIsolation of Natural Naphthoquinones from Juglans regia and In Vitro Antioxidant and Cytotoxic Studies of Naphthoquinones and the Synthetic Naphthofuran Derivatives, SDS of cas: 924-99-2, the publication is Russian Journal of Bioorganic Chemistry (2018), 44(3), 346-353, database is CAplus.

The naphthoquinones and their derivatives containing hydroxyl group exhibit wide range of pharmacol. activities, such as antioxidant, antibacterial, antiviral, anticancer, antimalarial, and antifungal activities. In particular, the antioxidant and anticancer behaviors of these compounds continue to draw attention of researchers. In the present communication, three natural naphthoquinones-juglone, lawsone, and plumbagin-isolated from the chloroform extract of nutshells of Juglans regia Linn. and two 1,4-naphthoquinone derivatives-ethyl-5-hydroxynaphtho[ 1,2-b]furan-3-carboxylate and diethylnaphtho[1,2-b:4,3-b′]difuran-3,4-dicarboxylate-and three 5-hydroxy- 1,4-naphthoquinone derivatives-diethyl-7-hydroxynaphtho[1,2-b:4,3-b′]difuran-3,4-dicarboxylate,4-ethoxycarbonyl- 7-hydroxynaphtho[1,2-b:4,3-b′]difuran-3-carboxylic acid, and 7-hydroxynaphtho[1,2-b:4,3-b′]difuran-3,4- dicarboxylic acid were synthesized and examined for their in vitro antioxidant activity using 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azino-bis-3-ethylbenzthiazoline-6-sulfonic acid (ABTS) bioassays. The 5-hydroxy-1,4-naphthoquinone derivatives displayed almost equivalent scavenging activity in DPPH assay and higher activity in ABTS assay relative to ascorbic acid. On the other hand, naphthoquinones Juglone and Plumbagin showed lesser antioxidant activity, but higher cytotoxic activity than naphthofurans except for di-Et naphtho[1,2-b:4,3-b′]difuran-3,4-dicarboxylate, which showed excellent cytotoxic activity.

Russian Journal of Bioorganic Chemistry published new progress about 924-99-2. 924-99-2 belongs to esters-buliding-blocks, auxiliary class Alkenyl,Amine,Aliphatic hydrocarbon chain,Ester, name is Ethyl 3-(dimethylamino)acrylate, and the molecular formula is C7H13NO2, SDS of cas: 924-99-2.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Zahra, Jalal A. published the artcileSynthesis of some ethyl 3-(aryldiazenyl)-7-oxodihydropyrido[2,3-f]quinoxaline-8-carboxylates, Category: esters-buliding-blocks, the publication is Zeitschrift fuer Naturforschung, B: Chemical Sciences (2007), 62(8), 1045-1051, database is CAplus.

Et 7,8-diamino-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate (6) and its free acid were prepared by chem. reduction of the resp. 7-azido-8-nitroquinoline. Consecutive nucleophilic addition and cyclocondensation reactions of 6 with α-acetyl-N-arylhydrazonoyl chlorides in EtOH and NEt₃ are site-selective and yield the corresponding 3-(arylazo)-2-methylpyrido[2,3-f]quinoxalines.

Zeitschrift fuer Naturforschung, B: Chemical Sciences published new progress about 924-99-2. 924-99-2 belongs to esters-buliding-blocks, auxiliary class Alkenyl,Amine,Aliphatic hydrocarbon chain,Ester, name is Ethyl 3-(dimethylamino)acrylate, and the molecular formula is C8H5F3O3, Category: esters-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Nishimura, Yoshio published the artcileSynthesis of 6-unsubstituted 2-oxo, 2-thioxo, and 2-amino-3,4-dihydropyrimidines and their antiproliferative effect on HL-60 cells, Computed Properties of 924-99-2, the publication is Tetrahedron Letters (2020), 61(28), 151967, database is CAplus.

A general and efficient synthetic method for 6-unsubstituted 3,4-dihydropyrimidin-2(1H)-thiones and -ones I (R = H, C₆H₅, 4-ClC₆H₄, etc., X = S, O) has been developed. In three-component reactions, the reactivity of reagents serving as the C5-C6 fragment of the dihydropyrimidine ring was compared. The reaction of thiourea or urea, aldehydes RCHO, and Et 3-(dimethylamino)acrylate in the presence of a catalytic amount of AlCl₃ by smooth heating proceeds to give I in high yields. Synthetic novelty of the protocol are as follows: (1) Lewis acid-mediated reaction, (2) good to high yields, and (3) broad scope as for aldehydes and ureas. Hitherto unavailable 6-unsubstituted 2-aminodihydropyridimidines II (R = n-Pr, Ph) have been obtained from the 2-thioxo derivative I (X = S) by a stepwise method involving substitution reaction with the amine at the 2-position. The 6-unsubstituted compounds I and 6-Me derivatives III (R = cyclohexyl, n-Pr) were assessed for their antiproliferative effect on the human promyelocytic leukemia cell line, HL-60. The 4-propyl-6-Me derivative III (R = n-Pr) showed relatively strong activity with the IC₅₀ value of 952 nM.

Tetrahedron Letters published new progress about 924-99-2. 924-99-2 belongs to esters-buliding-blocks, auxiliary class Alkenyl,Amine,Aliphatic hydrocarbon chain,Ester, name is Ethyl 3-(dimethylamino)acrylate, and the molecular formula is C7H13NO2, Computed Properties of 924-99-2.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Al-Hiari, Yusuf M. published the artcileFluoroquinolones: novel class of gastrointestinal dietary lipid digestion and absorption inhibitors, Name: Ethyl 3-(dimethylamino)acrylate, the publication is Medicinal Chemistry Research (2014), 23(7), 3336-3346, database is CAplus.

Pancreatic triacylglycerol lipase (PL) has been reported as an interesting pharmacol. target for the management of dyslipidemia, atherosclerosis, and obesity. In the current study, a 4-quinoline-3-carboxylic acid system has been identified as a potent inhibitor of PL. Three new fluoroquinolones (11, 12, (I) and 13 (II)) were synthesized and evaluated in vitro with respect to their anti-lipase efficacy and potency properties and gave IC₅₀ values in the range of 18.4-29.1 μM against PL. The IC₅₀ of the standard drug orlistat was 0.2 μM. The inhibitory activities of these compounds were supported by docking studies, which suggested that they acted according to a similar mechanism to that of the known drug orlistat. In conclusion, these effective PL inhibitors could be used to advance the development of anti-obesity drugs via the regulation of the entire gastrointestinal lipolysis process.

Medicinal Chemistry Research published new progress about 924-99-2. 924-99-2 belongs to esters-buliding-blocks, auxiliary class Alkenyl,Amine,Aliphatic hydrocarbon chain,Ester, name is Ethyl 3-(dimethylamino)acrylate, and the molecular formula is C7H13NO2, Name: Ethyl 3-(dimethylamino)acrylate.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Sato, Motohide published the artcileQuinolone Carboxylic Acids as a Novel Monoketo Acid Class of Human Immunodeficiency Virus Type 1 Integrase Inhibitors, SDS of cas: 924-99-2, the publication is Journal of Medicinal Chemistry (2009), 52(15), 4869-4882, database is CAplus and MEDLINE.

The synthesis and detailed structure-activity relationship of quinolonecarboxylic acids as a novel monoketo acid class of HIV-1 integrase inhibitors was presented. Compounds I (R = t-Bu), which showed an IC₅₀ of 5.8 nM in the strand transfer assay and an ED₅₀ of 0.6 nM in the antiviral assay, and I (R = i-Pr), which had an IC₅₀ of 7.2 nM and an ED₅₀ of 0.9 nM, were the most potent compounds in this class. The monoketo acid I (R = i-Pr) was much more potent at inhibiting integrase-catalyzed strand transfer processes than 3′-processing reactions, as is the case with the keto-enol acids. Elvitegravir I (R = i-Pr) was chosen as a candidate for further studies and was reported as being in phase 3 clin. trials.

Journal of Medicinal Chemistry published new progress about 924-99-2. 924-99-2 belongs to esters-buliding-blocks, auxiliary class Alkenyl,Amine,Aliphatic hydrocarbon chain,Ester, name is Ethyl 3-(dimethylamino)acrylate, and the molecular formula is C7H13NO2, SDS of cas: 924-99-2.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Miyauchi, Rie published the artcileDesign, synthesis and biological evaluations of novel 7-[3-(1-aminocycloalkyl)pyrrolidin-1-yl]-6-desfluoro-8-methoxyquinolones with potent antibacterial activity against multi-drug resistant Gram-positive bacteria, Quality Control of 924-99-2, the publication is Bioorganic & Medicinal Chemistry (2009), 17(19), 6879-6889, database is CAplus and MEDLINE.

A series of novel 6-desfluoro [des-F(6)] and 6-fluoro-1-[(1R,2S)-2-fluorocyclopropan-1-yl]-8-methoxyquinolones bearing 3-(1-aminocycloalkyl)pyrrolidin-1-yl substituents at the C-7 position (1-6) was synthesized to obtain potent drugs for nosocomial infections caused by Gram-pos. pathogens. The des-F(6) compounds 4-6 exhibited at least four times more potent activity against representative Gram-pos. bacteria than ciprofloxacin or moxifloxacin. Among the derivatives, 7-[(3R)-3-(1-aminocyclopropan-1-yl)pyrrolidin-1-yl] derivative 4, which showed favorable profiles in preliminary toxicol. and non-clin. pharmacokinetic studies, exhibited potent antibacterial activity against clin. isolated Gram-pos. pathogens that had become resistant to one or more antibiotics.

Bioorganic & Medicinal Chemistry published new progress about 924-99-2. 924-99-2 belongs to esters-buliding-blocks, auxiliary class Alkenyl,Amine,Aliphatic hydrocarbon chain,Ester, name is Ethyl 3-(dimethylamino)acrylate, and the molecular formula is C7H13NO2, Quality Control of 924-99-2.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Schwalbe, Thomas published the artcileSynthesis of a library of Ciprofloxacin analogues by means of sequential organic synthesis in microreactors, Name: Ethyl 3-(dimethylamino)acrylate, the publication is QSAR & Combinatorial Science (2005), 24(6), 758-768, database is CAplus.

The realm of combinatorial chem. is strongly based on the concept of parallel chem. and its ease of automation. Although this batch-type approach in general may be considered a success story, some limitations remain rarely addressable by conventional approaches. Particularly, scaling-up problems such as the resynthesis of multi-gram amounts of active compounds as well as the synthesis of building blocks and scaffolds in large amounts may prove to be problematic. The authors’ expertise in continuous chem. prompted them to develop a micro-reaction system for sequential organic synthesis that should overcome these limitations. In the present contribution a suitable system as well as its application to the first library approach towards (fluoro)quinolone antibiotics, such as Ciprofloxacin, solely using micro-reaction technol. is described. A known one-pot batch procedure for the synthesis of this compound class was split in its individual reaction steps, which were successfully adapted to a continuous conduct. After some optimization studies the overall sequence was suitable for chem. diversification. Particularly it was shown, that the first step of the synthesis – the acylation reaction of a β-dimethylamino acrylate with trifluoro-benzoic acid chloride – was accessible to synthesis of high quantities without any difficulties to yield a primary building block suitable for subsequent library synthesis. In a first diversification step, the Michael addition of a set of primary amines was followed by nucleophilic ring closure providing the difluoroquinolone system, which was subjected to a second diversification step by means of a nucleophilic aromatic substitution reaction. Thus, a number of Ciprofloxacin analogs could be synthesized in good overall yield and purity. Isolated yields ranged from 71 to 85% in the first diversification step and from 59 to 99% in the second step.

QSAR & Combinatorial Science published new progress about 924-99-2. 924-99-2 belongs to esters-buliding-blocks, auxiliary class Alkenyl,Amine,Aliphatic hydrocarbon chain,Ester, name is Ethyl 3-(dimethylamino)acrylate, and the molecular formula is C12H13NO3, Name: Ethyl 3-(dimethylamino)acrylate.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Gu, Hai-ning published the artcileStudy on new process of synthesizing levofloxacin, Safety of Ethyl 3-(dimethylamino)acrylate, the publication is Gaoxiao Huaxue Gongcheng Xuebao (2005), 19(5), 708-711, database is CAplus.

New process for preparing the fluoroquinolone antibacterial drug levofloxacin was described. The object compound was prepared from 2,3,4,5-tetrafluorobenzoic acid, via acyl chlorination, Et N,N-dimethylamino-acrylate coupling, S-(+)-2-aminopropanol displacement, cyclization, hydrolysis, and finally N-methylpiperazine condensation, the total yield is 52.3%. Comparing to the old process conventionally used at present, the application of the new starting material Et N, N-dimethylamino-acrylate can curtail three reaction steps, they are the di-Et malonate condensation, partial hydrolysis decarboxylation and triethylorthoformate condensation. New process has many advantages, such as simple procedure, short reaction period, high optical purity, cheaper raw material, higher yield. So it should have a good prospect for industrial application.

Gaoxiao Huaxue Gongcheng Xuebao published new progress about 924-99-2. 924-99-2 belongs to esters-buliding-blocks, auxiliary class Alkenyl,Amine,Aliphatic hydrocarbon chain,Ester, name is Ethyl 3-(dimethylamino)acrylate, and the molecular formula is C7H13NO2, Safety of Ethyl 3-(dimethylamino)acrylate.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Gu, Hai-ning published the artcileSynthesis of Gatifloxacin hydrochloride, Computed Properties of 924-99-2, the publication is Zhejiang Daxue Xuebao, Lixueban (2005), 32(1), 66-68, 74, database is CAplus.

Gatifloxacin was prepared from 3-methoxy-2,4,5-triflurobenzoic acid via acylation, followed by coupling with Et N,N-dimethylaminoacrylate, replacement with cyclopropyl amine, after cyclization and hydrolysis, condensation with 2-methylpiperazine, further hydrolysis, and saltification, provided title product with overall yield 441.1%.

Zhejiang Daxue Xuebao, Lixueban published new progress about 924-99-2. 924-99-2 belongs to esters-buliding-blocks, auxiliary class Alkenyl,Amine,Aliphatic hydrocarbon chain,Ester, name is Ethyl 3-(dimethylamino)acrylate, and the molecular formula is C7H13NO2, Computed Properties of 924-99-2.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics