19393-83-0

Basic information

• Product Name: 4-AMINO-6-BROMO-7H-PYRROLO[2,3-D]PYRIMIDINE-5-CARBONITRILE
• Synonyms: 1H-Pyrrolo[2,3-d]pyrimidine-5-carbonitrile, 4-amino-6-bromo-;4-amino-6-bromo-1H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile;4-Amino-6-bromo-5-cyano-7H-pyrrolo[2,3-d]pyrimidine;4-Amino-6-bromo-5-cyano-7H-pyrrolo[2,3-d]pyrimidine 4-Amino-6-bromo-7-H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
• CAS NO: 19393-83-0
• Molecular Formula: C₇H₄BrN₅
• Molecular Weight: 238.0442
• Mol File: 19393-83-0.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 225 °C at 760 mmHg
• Flash Point: 89.9 °C
• Appearance: /
• Density: 2.05 g/cm³
• Vapor Pressure: 0.0883mmHg at 25°C
• Refractive Index: 1.802
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: 4-AMINO-6-BROMO-7H-PYRROLO[2,3-D]PYRIMIDINE-5-CARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINO-6-BROMO-7H-PYRROLO[2,3-D]PYRIMIDINE-5-CARBONITRILE(19393-83-0)
• EPA Substance Registry System: 4-AMINO-6-BROMO-7H-PYRROLO[2,3-D]PYRIMIDINE-5-CARBONITRILE(19393-83-0)

Safety Data

• Hazardous Substances Data: 19393-83-0(Hazardous Substances Data)

Usage

General Description

4-AMINO-6-BROMO-7H-PYRROLO[2,3-D]PYRIMIDINE-5-CARBONITRILE is a chemical compound with the molecular formula C7H3BrN6. It is a pyrrolopyrimidine derivative and contains a carbonitrile functional group. 4-AMINO-6-BROMO-7H-PYRROLO[2,3-D]PYRIMIDINE-5-CARBONITRILE has potential application in pharmaceutical and agrochemical industries due to its biological activity. It may also be used as a building block in organic synthesis for the preparation of various heterocyclic compounds. Its unique structure and properties make it a valuable compound for medicinal and chemical research.

InChI:InChI=1/C7H4BrN5/c8-5-3(1-9)4-6(10)11-2-12-7(4)13-5/h2H,(H3,10,11,12,13)

Upstream product

• 98130-58-6 2-amino-5-bromo-1H-pyrrole-3,4-dicarbonitrile 
• 3473-63-0 formamidine acetic acid 
• 670-54-2 ethenetetracarbonitrile 
• 110089-43-5 2-bromo-5-(ethoxymethyleneamino)pyrrole-3,4-dicarbonitrile 
• 122-51-0 orthoformic acid triethyl ester 

Downstream Products

• 729595-79-3 (2R,3R,4R,5R)-2-(4-amino-6-bromo-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(benzoyloxymethyl)-3-methyltetrahydrofuran-3,4-diyl dibenzoate 
• 120386-06-3 2-amino-5-cyano-7-<(2-hydroxyethoxy)methyl>pyrrolo<2,3-d>pyrimidine 
• 1350887-25-0 4-amino-6-(3-bromophenyl)-5-cyano-7-(2,3,5-tri-O-benzoyl-β-L-xylofuranosyl)pyrrolo[2,3-d]pyrimidine 
• 1350887-26-1 4-amino-6-(1H-pyrrol-2-yl)-5-cyano-7-(2,3,5-tri-O-benzoyl-β-L-xylofuranosyl)pyrrolo[2,3-d]pyrimidine 
• 1350887-27-2 4-amino-6-(thiophen-2-yl)-5-cyano-7-(2,3,5-tri-O-benzoyl-β-L-xylofuranosyl)pyrrolo[2,3-d]pyrimidine 
• 1350887-28-3 4-amino-6-(furan-2-yl)-5-cyano-7-(2,3,5-tri-O-benzoyl-β-L-xylofuranosyl)pyrrolo[2,3-d]pyrimidine 
• 1350887-29-4 4-amino-6-(p-tolyl)-5-cyano-7-(β-L-xylofuranosyl)pyrrolo[2,3-d]pyrimidine 
• 1350887-30-7 4-amino-6-(4-methoxyphenyl)-5-cyano-7-(β-L-xylofuranosyl)pyrrolo[2,3-d]pyrimidine 
• 1350887-31-8 4-amino-6-(3-methoxyphenyl)-5-cyano-7-(β-L-xylofuranosyl)pyrrolo[2,3-d]pyrimidine 
• 1350887-32-9 4-amino-6-(4-(tert-butyl)phenyl)-5-cyano-7-(β-L-xylofuranosyl)pyrrolo[2,3-d]pyrimidine 
• 1350887-33-0 4-amino-6-(4-bromophenyl)-5-cyano-7-(β-L-xylofuranosyl)pyrrolo[2,3-d]pyrimidine 
• 1350887-34-1 4-amino-6-(3-bromophenyl)-5-cyano-7-(β-L-xylofuranosyl)pyrrolo[2,3-d]pyrimidine 
• 1350887-36-3 4-amino-6-(p-tolyl)-7-(β-L-xylofuranosyl)pyrrolo[2,3-d]pyrimidine-5-carboxamide 
• 1350887-38-5 4-amino-6-(3-methoxyphenyl)-7-(β-L-xylofuranosyl)pyrrolo[2,3-d]pyrimidine-5-carboxamide 

Relevant articles and documents

The synthesis and evaluation of new carbocyclic pyrrolo[2,3-d]pyrimidine nucleoside analogs

New carbocyclic pyrrolo[2,3-d]pyrimidine nucleoside analogs were synthesized with the key intermediate, 4-amino-6-bromo-5-cyanopyrrolo[2,3- d]pyrimidine (2), by SN2 reaction. One of the products, 4-amino-6-bromo-1- cyclopentyl-1H-pyrrolo[2,3-d]pyrimidine-5-carboxamide (9), showed significant anti-proliferative activity to the human ovarian cancer PA-1 cells (IC50: 3.9 μM). Based on the biological effects and the functional group characteristics of the compound 9, other carbocyclic nucleoside analogs related to the compound 9 were synthesized with key intermediate 2 by a Pd(0)-catalyzed coupling reaction. As expected, syn-4-amino-6-bromo-7-[4-(methoxymethyl)-2- cyclopenten-1-yl]- 7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide (15) showed very similar antiproliferative activity (IC50: 2.6 μM) when compared to compound 9.

Effects of a novel carbocyclic analog of pyrrolo[2,3-d]pyrimidine nucleoside on pleiotropic induction of cell death in prostate cancer cells with different androgen responsiveness

Prostate cancer is the most frequently diagnosed cancer and is one of the leading causes of male cancer death in the world. Recently, in the course of our screening for a novel anticancer compound, we synthesized carbocyclic analogs of pyrrolo[2,3-d]pyrimidine nucleoside; compounds 5, and 6. In the current study, we report the effects of compound 5 on pleiotropic induction of cell death via up-regulation of AR-associated p21Cip1 protein in prostate cancer cells with different androgen responsiveness, such as LNCaP (androgen-dependent and -sensitive), LNCaPC4-2 (androgen-independent and -sensitive; androgen-refractory), and DU145 (androgen-independent and -insensitive) cells. The treatment of LNCaP cells with 6 μM compound 5 for 24 h stimulated the androgen receptor (AR) activity and dramatically up-regulated transcription (56-fold) of p21Cip1, which, in turn, induces typical apoptosis in the cells. However, induction of apoptosis through up-regulation (23-fold) of AR-associated p21Cip1 achieved in LNCaPC4-2 cells was possible by intensive cell treatment with compound 5 (9 μM, 48 h), because the cells are less sensitive and independent to androgen than LNCaP cells. Furthermore, 6 μM compound 5-treated DU145 cells, which exhibit extremely low AR activation due to no androgen responsiveness and dependency, showed neither up-regulation of p21Cip1 nor apoptotic induction. Instead, a different type of cell death, autophagy-like death through the LC3B-associated autophagosome formation, was obviously induced in DU145 cells. Taken together, our results suggest that pleiotropic induction of prostate cancer cell death by compound 5 is determined by how efficiently and how abundantly androgen-dependent activation of the AR occurs, whereas compound 6 shows no induction of apoptosis in LNCaP cells.

Design and Synthesis of Pyrrolo[2,3-d]pyrimidine-Derived Leucine-Rich Repeat Kinase 2 (LRRK2) Inhibitors Using a Checkpoint Kinase 1 (CHK1)-Derived Crystallographic Surrogate

Inhibitors of leucine-rich repeat kinase 2 (LRRK2) and mutants, such as G2019S, have potential utility in Parkinson’s disease treatment. Fragment hit-derived pyrrolo[2,3-d]pyrimidines underwent optimization using X-ray structures of LRRK2 kinase domain surrogates, based on checkpoint kinase 1 (CHK1) and a CHK1 10-point mutant. (2R)-2-Methylpyrrolidin-1-yl derivative 18 (LRRK2 G2019S cKi0.7 nM, LE 0.66) was identified, with increased potency consistent with an X-ray structure of 18 /CHK1 10-pt. mutant showing the 2-methyl substituent proximal to Ala147 (Ala2016 in LRRK2). Further structure-guided elaboration of 18 gave the 2-[(1,3-dimethyl-1H-pyrazol-4-yl)amino] derivative 32 . Optimization of 32 afforded diastereomeric oxolan-3-yl derivatives 44 and 45 , which demonstrated a favorablein vitroPK profile, although they displayed species disconnects in thein vivoPK profile, and a propensity for P-gp- and/or BCRP-mediated efflux in a mouse model. Compounds 44 and 45 demonstrated high potency and exquisite selectivity for LRRK2 and utility as chemical probes for the study of LRRK2 inhibition.