4815-30-9

Basic information

• Product Name: DIETHYL 5-AMINO-3-METHYL-2,4-THIOPHENEDICARBOXYLATE
• Synonyms: IFLAB-BB F1386-0052;DIETHYL 5-AMINO-3-METHYL-2,4-THIOPHENEDICARBOXYLATE;DIETHYL 5-AMINO-3-METHYLTHIOPHENE-2,4-DICARBOXYLATE;DIETHYL 2-AMINO-4-METHYLTHIOPHENE-3,5-DICARBOXYLATE;ART-CHEM-BB B000492;AURORA 879;ASISCHEM S46503;2,4-THIOPHENEDICARBOXYLIC ACID, 5-AMINO-3-METHYL-, DIETHYL ESTER
• CAS NO: 4815-30-9
• Molecular Formula: C₁₁H₁₅NO₄S
• Molecular Weight: 257.31
• EINECS: 225-388-0
• Product Categories: Esters;Thiophenes & Benzothiophenes;Thiophenes & Benzothiophenes;Building Blocks;Heterocyclic Building Blocks;Thiophenes
• Mol File: 4815-30-9.mol

Chemical Properties

• Melting Point: 105-108 °C(lit.)
• Boiling Point: 372.6 °C at 760 mmHg
• Flash Point: 179.1 °C
• Appearance: Slightly yellow to beige-yellow/Crystalline Powder
• Density: 1.3137 (rough estimate)
• Vapor Pressure: 9.51E-06mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• PKA: -0.53±0.10(Predicted)
• CAS DataBase Reference: DIETHYL 5-AMINO-3-METHYL-2,4-THIOPHENEDICARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIETHYL 5-AMINO-3-METHYL-2,4-THIOPHENEDICARBOXYLATE(4815-30-9)
• EPA Substance Registry System: DIETHYL 5-AMINO-3-METHYL-2,4-THIOPHENEDICARBOXYLATE(4815-30-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-60-37
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 4815-30-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
DIETHYL 5-AMINO-3-METHYL-2,4-THIOPHENEDICARBOXYLATE is used as a reagent for the synthesis of novel pyrazolo-pyrimidinones, which act as dipeptidyl peptidase IV (DPP-IV) inhibitors. These inhibitors play a significant role in the management of diabetes by regulating glucose levels in the body.
Additionally, DIETHYL 5-AMINO-3-METHYL-2,4-THIOPHENEDICARBOXYLATE is used in the synthesis of N-phenylthieno[2,3-d]pyrimidin-4-amines. These compounds serve as inhibitors of fibroblast growth factor receptor 1 (FGFR1), making them potential candidates for the development of anticancer agents. By targeting FGFR1, these inhibitors can potentially disrupt the growth and proliferation of cancer cells, offering a new avenue for cancer treatment.

InChI:InChI=1/C11H15NO4S/c1-4-15-10(13)7-6(3)8(17-9(7)12)11(14)16-5-2/h4-5,12H2,1-3H3

Upstream product

• 15933-07-0 Ethyl 2-oxobutanoate 
• 105-56-6 ethyl 2-cyanoacetate 
• 141-97-9 ethyl acetoacetate 

Downstream Products

• 101130-12-5 5-Methyl-4-oxo-2-((E)-styryl)-3,4-dihydro-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl ester 
• 17417-67-3 3,4-Dihydro-5-methyl-4-oxothieno<2,3-d>pyrimidin-6-carbonsaeure-ethylester 
• 89567-06-6 ethyl 2-(chloromethyl)-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate 
• 23903-53-9 4-Hydroxy-2,5-dimethyl-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl ester 
• 23903-53-9 3,4-Dihydro-2,5-dimethyl-4-oxothieno<2,3-d>pyrimidin-6-carbonsaeure-ethylester 
• 304898-01-9 5-isothiocyanato-3-methyl-2,4-thiophenedicarboxylic acid diethyl ester 

Relevant articles and documents

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.

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

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.

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.

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.

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.

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:

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.

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.

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.