173458-92-9

Basic information

• Product Name: 1H-Pyrrole-3-carboxylic acid, 2-aMino-5-(4-Methoxyphenyl)-, ethyl ester
• Synonyms: 1H-Pyrrole-3-carboxylic acid, 2-aMino-5-(4-Methoxyphenyl)-, ethyl ester;ethyl 2-amino-5-(4-methoxyphenyl)-1H -pyrrole-3-carboxylate
• CAS NO: 173458-92-9
• Molecular Formula: C₁₄H₁₆N₂O₃
• Molecular Weight: 260.28844
• Mol File: 173458-92-9.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 524.0±50.0 °C(Predicted)
• Appearance: /
• Density: 1.217±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 18.58±0.50(Predicted)
• CAS DataBase Reference: 1H-Pyrrole-3-carboxylic acid, 2-aMino-5-(4-Methoxyphenyl)-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrole-3-carboxylic acid, 2-aMino-5-(4-Methoxyphenyl)-, ethyl ester(173458-92-9)
• EPA Substance Registry System: 1H-Pyrrole-3-carboxylic acid, 2-aMino-5-(4-Methoxyphenyl)-, ethyl ester(173458-92-9)

Safety Data

• Hazardous Substances Data: 173458-92-9(Hazardous Substances Data)

Usage

Structure

Ethyl ester derivative of 1H-Pyrrole-3-carboxylic acid, 2-amino-5-(4-methoxyphenyl)-

Synonyms

Ethyl 2-amino-5-(p-methoxyphenyl)-1H-pyrrole-3-carboxylate

Use in medicinal chemistry

Building block for the synthesis of various pharmaceuticals and bioactive compounds

Potential applications

Drug discovery and development, research and development for the synthesis of new chemical entities with therapeutic potential

Structural features

Contains a pyrrole ring, an amino group, a methoxy group, and an ethyl ester group

Biological activities

Not specified in the provided material, but may have potential due to its structural features.

Upstream product

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• 2632-13-5 2-Bromo-4'-methoxyacetophenone 
• 105-56-6 ethyl 2-cyanoacetate 
• 27317-59-5 Ethyl 3-ethoxy-3-iminopropionate 
• 141-52-6 sodium ethanolate 
• 2318-25-4 ethyl 3-ethoxy-3-iminopropanoate hydrochloride 
• 50551-10-5 ethyl amidinoacetate 

Downstream Products

• 1011717-24-0 (R)-N-(1-(4-fluorophenyl)ethyl)-6-(4-methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine 
• 1220121-04-9 C₂₁H₁₉FN₄O 
• 1220121-05-0 C₂₁H₁₉FN₄O 
• 1220121-06-1 C₂₀H₁₇FN₄O 
• 1220121-07-2 C₂₀H₁₇FN₄O 
• 1220121-08-3 C₂₀H₁₇FN₄O 
• 173459-03-5 4-chloro-6-(4-methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidine 
• 1350639-66-5 (R)-N-(1-(4-bromophenyl)ethyl)-6-(4-methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine 
• 1350639-67-6 (R)-6-(4-methoxyphenyl)-N-(1-p-tolylethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine 
• 1350639-68-7 6-(4-methoxyphenyl)-N-(1-(4-(trifluoromethyl)phenyl)ethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine 
• 1350639-69-8 6-(4-methoxyphenyl)-N-(1-o-tolylethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine 
• 1350639-70-1 6-(4-methoxyphenyl)-N-(1-m-tolylethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine 
• 1011717-27-3 N-benzyl-6-(4-methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine 
• 1350639-71-2 (R)-6-(4-methoxyphenyl)-N-(1-phenylpropyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine 

Relevant articles and documents

Activity of 6-aryl-pyrrolo[2,3-d]pyrimidine-4-amines to Tetrahymena

A series 6-aryl-pyrrolo[2,3-d]pyrimidine-4-amines (43 compounds), some of which are epidermal growth factor tyrosine kinase inhibitors, were tested for their protozoal toxicity using an environmental Tetrahymena strain as model organism. The protozoacidal activity of the analogues was found to be highly dependent on a 4-hydroxyl group at the 6-aryl ring, and a chiral 1-phenylethanamine substituent in position 4. Further, the potency was affected by the aromatic substitution pattern of the phenylethanamine: the unsubstituted, the meta-fluoro and the para-bromo substituted derivatives had the lowest minimum protozoacidal concentrations (8-16 μg/mL). Surprisingly, both enantiomers were found to have high potency suggesting that this compound class could have several modes of action. No correlation was found between the compounds protozoacidal activity and the in vitro epidermal growth factor receptor tyrosine kinase inhibitory potency. This suggests that the observed antimicrobial effects are related to other targets. Testing towards a panel of kinases indicated several alternative modes of action.

1H,13C and19FNMR data of N-substituted 6-(4-methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amines in DMSO-d6

Chemical shift assignment of seven N-substituted 6-(4-methoxyphenyl)-7H- pyrrolo[2, 3-d]pyrimidin-4-amines, six of which are fluorinated, have been performed based on 1H, 13C, 19F, and 2D COSY, HMBC and HSQC experiments. C

MULTI-FUNCTIONAL SMALL MOLECULES AS ANTI-PROLIFERATIVE AGENTS

The present invention relates to the compositions, methods, and applications of a novel approach to selective inhibition of several cellular or molecular targets with a single small molecule. More specifically, the present invention relates to multi-functional small molecules wherein one functionality is capable of inhibiting histone deacetylases (HDAC) and the other functionality is capable of inhibiting a different cellular or molecular pathway involved in aberrant cell proliferation, differentiation or survival.