cas 4815-30-9, DIETHYL 5-AMINO-3-METHYL-2,4-THIOPHENEDICARBOXYLATE

Articles about 4815-30-9Total 27 be found

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Triester-amide based on thiophene and ricinoleic acid as an innovative primary plasticizer for poly(vinyl chloride)
It is necessary to replace phthalate plasticizers which are used in PVC as they are found to be carcinogenic and hazardous to human health. They can be substituted with other bio based plasticizers which are non toxic. We have synthesized a triester amide of thiophene (THPRABA) with ricinoleic acid (RA) and benzoic acid (BA) reacting with a diester derivative of 2-aminothiophene (THP) which itself is procured by using Gewald multicomponent synthesis. The structure of the THPRABA was confirmed by IR, 1H NMR, acid value, and hydroxyl value. The DOP was replaced entirely by THPRABA as a plasticizer for PVC in all samples with a varying proportion of THPRABA from 10 phr to 50 phr with a fixed heat stabilizer content as 5 phr. The incorporation of THPRABA shows a decrease in tensile and mechanical properties, glass transition temperature (Tg), crystallinity and shore hardness properties. The yellowness index shows darkening of PVC sheets with a decrease in whiteness. Hence it can replace DOP in plasticizer application successfully in some application areas of PVC.
Satavalekar, Sneha D.,Savvashe, Prashant B.,Mhaske, Shashank T.
p. 115101 - 115112
(2016)
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Synthesis and antiproliferative activity of some new thieno[2,3-d ]pyrimidin-4(3H)-ones containing 1,2,4-triazole and 1,3,4-thiadiazole moiety
Some new thieno[2,3-d]pyrimidin-4(3H)-ones containing 1,2,4-triazole and 1,3,4-thiadiazole moiety were synthesized using thieno[2,3-d]pyrimidin-3(4H)-yl)acetohydrazides as precursors in order to determine their cytotoxicity. Compounds 5, 7-8 and 10-18 wer
Mavrova, Anelia Ts.,Wesselinova, Diana,Tsenov, Jordan A.,Lubenov, Lubomir A.
p. 676 - 683
(2014)
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Efficient synthesis of new thieno[2,3-d]pyrimidin-4(3H)-one derivatives for evaluation as anticancer agents
Thieno[2,3-d]pyrimidinones were reported to act as potent anticancer agents; in this work, a series of new substituted thieno[2,3-d]pyrimidinone (6) were synthesized via the aza-Wittig reaction in satisfactory yields. The structures of these compounds were confirmed by elemental analysis, IR, 1H-NMR, and mass spectral data, and compound 6h was further analyzed by single crystal X-ray diffraction. Cytotoxic effect of all the compounds was carried out on human breast and lung cancer cell lines (MCF-7 and SPC-A-1, A459). Compound 6f exhibited the best inhibition activities against A459 with IC50 4.1 μM.
Hu, Yang-Gen,Zheng, Ai-Hua,Li, Gao-Jun,Dong, Meng-Zhu,Ye, Fang,Sun, Feng,Liu, Zheng-Yun,Li, Wen
p. E84-E88
(2014)
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Synthesis, computational, spectroscopic, hirshfeld surface, electronic state and molecular docking studies on diethyl-5-amino-3-methylthiophene-2,4-dicarboxylate
Diethyl 5-amino-3-methylthiophene-2,4-dicarboxylate (DAMC) was synthesized, characterized, and investigated theoretically and by experimental spectroscopy. Surface analysis by Hirshfeld, and Spectrochemical analysis by NMR (1H NMR and 13C NMR), FT-IR, and UV–Visible were performed. 1H NMR and 13C NMR shifts were estimated by the GIAO method and results were compared with experimental spectra. The energy difference between HOMO and LUMO revealed the chemical activity of the titled molecule such as Ionization Energy, Electron Affinity, Electronegativity. The molecular docking was carried out with 12 different protein receptors on a molecule to find the best ligand–protein interactions. Drug-likeness was also carried out.
Fatima, Aysha,Javed, Saleem,Khanum, Ghazala,Kumar Srivastava, Sanjay,Siddiqui, Nazia,Verma, Indresh
(2021/10/16)

Molecular design, synthesis and in vitro biological evaluation of thienopyrimidine–hydroxamic acids as chimeric kinase HDAC inhibitors: a challenging approach to combat cancer
A series of thieno[2,3-d]pyrimidine-based hydroxamic acid hybrids was designed and synthesised as multitarget anti-cancer agents, through incorporating the pharmacophore of EGFR, VEGFR2 into the inhibitory functionality of HDAC6. Three compounds (12c, 15b and 20b) were promising hits, whereas (12c) exhibited potent VEGFR2 inhibition (IC50=185 nM), potent EGFR inhibition (IC50=1.14 μM), and mild HDAC6 inhibition (23% inhibition). Moreover, compound (15c) was the most potent dual inhibitor among all the synthesised compounds, as it exhibited potent EGFR and VEGFR2 inhibition (IC50=19 nM) and (IC50=5.58 μM), respectively. While compounds (20d) and (7c) displayed nanomolar selective kinase inhibition with EGFR IC50= 68 nM and VEGFR2 IC50= 191 nM, respectively. All of the synthesised compounds were screened in vitro for their cytotoxic effect on 60 human NCI tumour cell lines. Additionally, molecular docking studies and ADMET studies were carried out to gain further insight into their binding mode and predict the pharmacokinetic properties of all the synthesised inhibitors.
Abdel-Atty, Mona M.,Abouzid, Khaled A. M.,Farag, Nahla A.,Mowafy, Samar,Serya, Rabah A. T.
p. 1290 - 1312
(2021/07/09)

COMPOUND AS ACC INHIBITOR AND USE THEREOF
Disclosed are a class of compounds which are inhibitors of acetyl-CoA carboxylase (ACC) and the use thereof. In particular, provided are compounds as shown in formula I or isomers, pharmaceutically acceptable salts, solvates, crystals or prodrugs thereof, and methods for preparing the same, and pharmaceutical compositions comprising the compounds and the use of the compounds or compositions for treating and/or preventing diseases associated with ACC expression, such as fibrotic diseases, metabolic diseases, cancers or tissue hyperplasia diseases. The compound has a good inhibitory activity against ACC and shows good promise to be a therapeutic drug for fibrotic diseases, metabolic diseases, cancers or tissue hyperplasia diseases.
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Paragraph 0190; 0191

(2020/06/15)

COMPOUNDS, COMPOSITIONS, AND METHODS FOR MODULATING ANDROGEN RECEPTOR ACTIVITY
Inhibitors of androgen receptors that are thienopyrimidine derivatives corresponding to formula (I), and salts thereof, and associated compositions and methods of treatment:
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Page/Page column 13; 46; 47

(2020/07/15)

Preparation method of thienopyrimidinedione compound
The invention provides a preparation method of a compound shown as a general formula c, wherein the definition of substituent is as defined in the specification. Please see the specification for the formula.
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Paragraph 0051-0054

(2020/02/20)

THIENOPYRIMIDINE DERIVATIVE AND USE THEREOF IN MEDICINE
The present invention relates to a thienopyrimidine derivative and use thereof in medicine, and also to a pharmaceutical composition containing the compound. The compound or pharmaceutical composition is used for inhibiting acetyl-CoA carboxylase (ACC). The present invention also relates to a method of preparing such compound and pharmaceutical composition, as well as their use in the treatment or prevention of diseases regulated by acetyl-CoA carboxylase in mammals, especially in humans.
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Paragraph 0160

(2018/08/12)

PYRAZOLE ACC INHIBITORS AND USES THEREOF
The invention provides pyrazole compounds of formula I inhibiting Acetyl CoA Carboxylase (ACC), compositions and uses thereof for the treatment of obesity or as fungicides.
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Paragraph 0386; 0392

(2017/06/21)

ESTER ACC INHIBITORS AND USES THEREOF
The present invention provides ester compounds useful as inhibitors of Acetyl CoA Carboxylase (ACC), compositions thereof, and methods of using the same.
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Paragraph 0440-0441

(2017/07/06)

Synthesis, anticancer activity and photostability of novel 3-ethyl-2-mercapto-thieno[2,3-d]pyrimidin-4(3H)-ones
Some derivatives of 3-ethyl-2-mercapto-thieno[2,3-d]pyrimidin-4(3H)-ones were synthesized using ethyl 2-aminothiophene-3-carboxylates as precursors in order to estimate their cytotoxicity, respectively proliferative activity. Thienopyrimidinones containing thiosemicarbazide as well as 1,3,4-thiadiazole moieties were evaluated for their cytotoxical effect on four cancer cell lines: HT-29, breast cancer cells MDA-MB-231, HeLa, HepG2 as well as human diploid cell line Lep-3. Compounds 5b, 6a and 6b revealed cytotoxicity to the four studied cancer cell lines. The highst cytotoxicity against MDA-MB-31 exhibited the thiosemicarbazide 5b with IC502.31.10?4?μM, but most active towards HT-29?cell lines was thienopyrimidine 6c with IC500.001?μM. Compound 6a showed the highest inhibitory activity with IC50- 0.99?μM to human liver carcinoma HepG2 cells and low cytotoxicity towards Lep3 (IC50?=?191?μM). The thienopyrimidine derivative linked to thiadiazole 6b was toxic to the four studied cancer cell lines, especially to HeLa (IC50–0.83?μM), and besides that the compound demonstrated toxicity to Lep 3?cells at very high concentration 89?×?103?μM. The solid-state photostability of the derivatives 5a-c and 6a-c was tested by irradiation with UV light. All of the studied compounds show solid-state photostability in 240?min of irradiation. Using MOE software molecular docking of the three ligands 5b, 6b and 7 was accomplished into an internal pocket formed by the activation segment and the P-loop ofV599EB-Raf. It was established that the binding of the ligands toV599EB-Raf promotes an inactive conformation of the enzyme.
Mavrova, Anelia Ts,Dimov, Stefan,Yancheva, Denitsa,Rangelov, Miroslav,Wesselinova, Diana,Tsenov, Jordan A.
p. 69 - 79
(2016/08/01)

Synthesis, characterization and in silico designing of diethyl-3-methyl-5-(6-methyl-2-thioxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxamido) thiophene-2,4-dicarboxylate derivative as anti-proliferative and anti-microbial agents
A series of eight compounds diethyl-3-methyl-5-(6-methyl-2-thioxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxamido) thiophene-2,4-dicarboxilate (KM10–17) analogues have been prepared by conventional methods and characterized by IR, Mass, NMR and elemental analysis. In silico docking studies on Human topoisomerase IIbeta (PDB Id: 3QX3) have been performed for all molecules (KM10–17) synthesized. The compounds were tested for in vitro anti-proliferative activity on VERO and 786-O cell lines. Out of all the synthesized compounds, KM11 & KM16 showed moderate activity on both cell lines. In vitro anti-microbial activity was also checked against Bacillus subtilis (BS), Staphylococcus aurous (SA), Pseudomonas aeruginosa (PA), Escherichia coli (EC) and Candida albicans (CA) by well diffusion method. The compound KM11 was found to have highest zone of inhibition against BS, SA, PA and EC. The molecules KM13 and KM16 exhibited good activity against CA. The compounds KM14 and KM16 indicated good zone of inhibition against BS.
Malani, Kalpesh,Thakkar, Sampark S.,Thakur, Mukund Chandra,Ray, Arabinda,Doshi, Hiren
p. 265 - 274
(2016/09/16)

Design and synthesis of novel protein kinase CK2 inhibitors on the base of 4-aminothieno[2,3-d]pyrimidines
An extension of our previous research work has resulted in a number of new ATP-competitive CK2 inhibitors that have been identified among 4-aminothieno[2,3-d]pyrimidine derivatives. The most active compounds obtained in the course of the research are 3-(5-p-tolyl-thieno[2,3-d]pyrimidin-4-ylamino)-benzoic acid, 5e (NHTP23, IC50 = 0.01 μM), 3-(5-phenyl-thieno[2,3-d]pyrimidin-4-ylamino)-benzoic acid, 5g (NHTP25, IC50 = 0.065 μM) and 3-(6-methyl-5-phenyl-thieno[2,3-d]pyrimidin-4-ylamino)-benzoic acid, 5n (NHTP33, IC50 = 0.008 μM). Structure-activity relationships of the tested 4-aminothieno[2,3-d]pyrimidine derivatives have been studied and their binding mode with ATP-acceptor site of CK2 has been proposed. A negative effect of intramolecular hydrogen bonding in the compounds' structure is discussed.
Ostrynska, Olga V.,Balanda, Anatoliy O.,Bdzhola, Volodymyr G.,Golub, Andriy G.,Kotey, Igor M.,Kukharenko, Olexander P.,Gryshchenko, Andrii A.,Briukhovetska, Nadiia V.,Yarmoluk, Sergiy M.
p. 148 - 160
(2016/04/05)

Basic Ionic Liquid [bmIm]OH-Mediated Gewald Reaction as Green Protocol for the Synthesis of 2-Aminothiophenes
A simple, efficient, and environmental friendly procedure was developed based on the Gewald reaction for the synthesis of 2-aminothiophenes using a basic ionic liquid [bmIm]OH as both catalyst and solvent. Besides being a green protocol, the method offers advantages of successful synthesis of a variety of alkyl, aryl, alkoxy, and alkylamino-2-aminothiophenes in good yields.
Kaki, Venkata Rao,Akkinepalli, Raghuram Rao,Deb, Pran Kishore,Pichika, Mallikarjuna Rao
p. 119 - 126
(2015/10/20)

ACC INHIBITORS AND USES THEREOF
The present invention provides compounds useful as inhibitors of Acetyl CoA Carboxylase (ACC), compositions thereof, and methods of using the same.
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Paragraph 0339; 0340; 0341

(2013/05/22)

Synthesis of some novel methyl- and ethyl-2-aminothiophene-3-carboxylate and related Schiff-bases
Methyl- and ethyl-2-amino thiophene-3-carboxylate derivatives 1(a-h) were synthesized by a simple one-pot condensation reaction of the ketone, elemental sulphur and methyl- or ethylcyanoacetate in the presence of morpholine as a catalyst. Further reaction of these compounds with salicylaldehyde gave related Schiff-bases, 2(a-e). Yields of products following recrystallization from ethanol were in the range of 70-85 %. 1H NMR and IR spectra and elemental analysis data were used to identification of these compounds.
Mobinikhaledi,Kalhor,Taheri
experimental part
p. 7399 - 7404
(2012/07/17)

Azo dyes
The azo dyes relate to thiophene azo dyes of the general formula: where R1 is Cyano or C1-C5 alkoxy carbonyl; R2 is hydrogen, halogene, C1-C2 alkyl, phenyl, or substituted phenyl; and R3 is C1-C5 alkoxy carbonyl, C1-C4 alkanoyl, benzoyl, phenyl, alkyl substituted phenyl, or alkoxy phenyl; or R2 and R3 are fused cycloalkane with C3-C5.
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Page/Page column 4-5

(2010/04/25)

Synthesis, biological and medicinal significance of S-glycosido-thieno[2,3-d]-pyrimidines as new anti-inflammatory and analgesic agents
Several 2-thioglycosides were prepared. Glycosylation of 2-thioxo-thieno[2,3-d]-pyrimidines 5a,b with 1-bromo-2,3,5-tri-O-acetyl-α-d-arabinofuranosyle 7, 2,3,4,6-tetra-O-acetyl-α-d-glucopyranosyl and galacto-pyranosyl bromide 8a,b gave the protected β-d-nuclosides 10a,b and 13a-d in high yields, which were transformed to deacetylated derivatives 14a,b and 15a-d. The structures of the compounds were elucidated by spectral and elemental analysis. Anti-inflammatory and Analgesic activities screening of the new compounds (at a dose of 100?mg/kg body weight) utilizing in vivo acute carrageenan-induced paw oedema standard method exhibited that the deacetylated derivatives 14a,b and 15a-d possess highly promising activities.
Hafez, Hend N.,El-Gazzar, Abdel-Rahman B.A.,Nawwar, Galal A.M.
scheme or table
p. 1485 - 1493
(2010/06/14)

Synthesis, antitrichinnellosis and antiprotozoal activity of some novel thieno[2,3-d]pyrimidin-4(3H)-ones containing benzimidazole ring
Some novel thieno[2,3-d]pyrimidin-4(3H)-ones containing benzimidazol-2-yl-thioethyl- and benzimidazol-2-yl-methanethioethyl moiety in second position of the pyrimidine ring were synthesized in order to determine their antitrichinellosis and antiprotozoal effects. The structures of the compounds were confirmed by IR, 1H NMR and elemental analysis. The antiparasitic screening showed that the benzimidazole derivatives of thieno[2,3-d]pyrimidin-4(3H)-ones exhibited higher activity against Trichinella spiralis in vitro in comparison albendazole. The most active compound, 2-[2-(5-nitro-1H-benzimidazol-1-yl)ethyl]-5,6,7,8-tetrahydro[1]benzothieno[2, 3-d]pyrimidin-4(3H)-one 22 revealed 95% activity at a dosage of 5 mg/kg mw after 24 h, while compounds 8 and 10 applied at the same dose showed efficacy of 90% after 48 h. The compound 2-{2-[(5(6)-nitro-1H-benzimidazol-2-yl)thio]ethyl}-5,6, 7,8-tetrahydro[1]-benzothieno[2,3-d]pyrimidin-4(3H)-one 11 exhibited 90% efficacy after 24 h. The pharmaco-therapeutic study in vivo on invaded with Lamblia muris white mice showed 100% effectiveness of the compounds 8, 10, 11, 13-15 and 22, 23 after five-days-treatment course.
Mavrova, Anelia Ts.,Vuchev, Dimitar,Anichina, Kameliya,Vassilev, Nikolay
experimental part
p. 5856 - 5861
(2011/01/03)

Design and synthesis of 3-pyrazolyl-thiophene, thieno[2,3-d]pyrimidines as new bioactive and pharmacological activities
Two series of 5-ethyl-2-amino-3-pyrazolyl-4-methylthiophenecarboxylate and 2-thioxo-N3-aminothieno[2,3-d]pyrimidines were prepared from 3,5-diethyl-2-amino-4-methylthio-phenecaboxylate and evaluated as anti-inflammatory, analgesic and ulcerogen
Hafez,El-Gazzar
experimental part
p. 5222 - 5227
(2009/05/07)

Efficient synthesis of substituted 2-amino-3-carbethoxythiophenes
A microwave-assisted method for the synthesis of a variety of thiophene o-aminoesters (2a-l) has been developed, starting from an appropriate aldehyde, methyl ketone or acetoacetate ester with ethyl cyanoacetate in the presence of elemental sulfur. Copyright Taylor & Francis Group, LLC.
Kathiravan,Shishoo,Chitre,Mahadik,Jain
p. 4273 - 4279
(2008/03/13)

Microwave accelerated Gewald reaction: synthesis of 2-aminothiophenes
Microwave-promoted synthesis of 2-aminothiophenes by multicomponent reactions of a ketone with an active nitrile and elemental sulfur under KF-alumina catalysis is described.
Sridhar, Madabhushi,Rao, Rayankula Mallikarjuna,Baba, Nanduri H.K.,Kumbhare, Ravindra M.
p. 3171 - 3172
(2007/10/03)

Synthesis of 2-aminothiophenes on ionic liquid phase support using the Gewald reaction
The first report of the use of task-specific ionic liquid as soluble support for the Gewald synthesis of 2-aminothiophenes is reported in this article. This synthetic method is simple and efficient, and the products are obtained in good to excellent yields with high purities, without the need for chromatographic purification. Copyright Taylor & Francis Group, LLC.
Hu, Yi,Wei, Ping,Huang, He,Han, Shi-Qing,Ouyang, Ping-Kai
p. 1543 - 1548
(2007/10/03)

Microwave-assisted gewald synthesis of 2-amimothio-phenes using functional ionic liquid as soluble support
A microwave-assisted liquid-phase Gewald synthesis of 2-aminothiophenes was developed using task-specific ionic liquid - [2-hydemim][BF4] as soluble support. This new synthetic method is simple and efficient, and the products are obtained in good to excellent yields with high purities, without the need for chromatographic purification.
Hu, Yi,Wei, Ping,Huang, He,Han, Shi-Qing,Ouyang, Ping-Kai
p. 375 - 380
(2007/10/03)

Microwave-assisted synthesis of 2-amino-thiophene-3-carboxylic derivatives under solvent-free conditions
Under microwave irradiation and solvent-free conditions, cyanoacetates (cyanoacetamides) react with ketones and sulphur in the presence of a small amount of morpholine to give 2-amino-thiophene-3-carboxylic derivatives. In particular, tetrahydro-benzo[b]thiophene-3-carboxylic acid N-aryl amides were synthesized in high yields of 84-95%. Copyright Taylor & Francis, Inc.
Huang, Wei,Li, Jian,Tang, Jing,Liu, Hong,Shen, Jianhua,Jiang, Hualiang
p. 1351 - 1357
(2007/10/03)

Organic reactions in ionic liquids: Gewald synthesis of 2-aminothiophenes catalyzed by ethylenediammonium diacetate
Ionic liquids based on 1-butyl-3-methylimidazolium tetrafluoroborate (BmimBF4) and 1-butyl-3-methylimidazolium hexafluorophosphate (BmimPF6) were used as reusable alternatives to volatile organic solvents (VOCs) for ethylenediammonium diacetate (EDDA) catalyzed Gewald synthesis of 2-aminothiophenes. Significant rate enhancement and improvement of the yield were observed. The ionic liquids containing catalyst EDDA were recycled several times with no decreases in yields and reaction rates.
Hu, Yi,Chen, Zhen-Chu,Le, Zhang-Gao,Zheng, Qin-Guo
p. 3801 - 3806
(2007/10/03)