19393-83-0

Usage

Uses

Used in Pharmaceutical Industry:
4-AMINO-6-BROMO-7H-PYRROLO[2,3-D]PYRIMIDINE-5-CARBONITRILE is used as a building block in organic synthesis for the preparation of various heterocyclic compounds. Its biological activity makes it a promising candidate for the development of new pharmaceuticals with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical industry, 4-AMINO-6-BROMO-7H-PYRROLO[2,3-D]PYRIMIDINE-5-CARBONITRILE may be utilized as a starting material for the synthesis of agrochemicals with pesticidal or herbicidal properties. Its unique structure and functional groups can contribute to the development of novel and effective agrochemicals.
Used in Organic Synthesis:
4-AMINO-6-BROMO-7H-PYRROLO[2,3-D]PYRIMIDINE-5-CARBONITRILE is used as a key intermediate in the synthesis of complex organic molecules. Its versatile structure allows for further functionalization and modification, making it a valuable compound for the preparation of a wide range of heterocyclic compounds with diverse applications in various fields.

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

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

Downstream Products

• 118043-66-6 4-amino-6-bromo-5-cyano-7-<<1,3-bis(benzyloxy)-2-propoxy>methyl>pyrrolo<2,3-d>pyrimidine 
• 120386-04-1 4-amino-5-cyano-7-<(2-acetoxyethoxy)methyl>pyrrolo<2,3-d>pyrimidine 
• 120386-05-2 4-amino-5-cyano-1-<(2-acetoxyethoxy)methyl>pyrrolo<2,3-d>pyrimidine 
• 141232-17-9 6-bromo-5-cyano-4-tritylaminopyrrolo<2,3-d>pyrimidine 
• 174019-77-3 4-amino-6-bromo-5-cyano-7-(2,3-di-O-benzoyl-5-deoxy-5-fluoro-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine 
• 174019-83-1 4-amino-6-bromo-5-cyano-7-(5-azido-2,3-di-O-benzoyl-5-deoxy-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine 
• 151707-53-8 (2R,3R,4R,5R)-2-(4-amino-6-bromo-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-((benzoyloxy)methyl)tetrahydrofuran-3,4-diyl dibenzoate 
• 332363-34-5 C₃₆H₃₁N₅O₇ 
• 332363-33-4 C₃₆H₂₉N₅O₇ 
• 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 
• 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 

Relevant academic research and scientific papers

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.

An expeditious total synthesis of 50-Deoxy-toyocamycin and 50-Deoxysangivamycin

In present paper, an expeditious total synthesis of naturally occurring 50-deoxytoyocamycin and 50-deoxysangivamycin was accomplished. Because of the introduction of a benzoyl group at N-6 of 4-amino-5-cyano-6-bromo-pyrrolo[2,3-d]pyrimidine, a Vorbrüggen glycosylation with 1,2,3-tri-O-acetyl-5-deoxy-β-D-ribofuranose afforded a completely regioselective N-9 glycosylation product, which is unambiguously confirmed by X-ray diffraction analysis. All of the involved intermediates were well characterized by various spectra.

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.

An improved synthesis of the versatile heterocycle, 4-amino-6-bromo-5- cyanopyrrolo [2,3-d]pyrimidine

A fast and efficient method was developed for the preparation of 4- amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidine from 2-amino-5-bromo-3,4- dicyanopyrrole, triethylorthoformate and ethanolic ammonia. Pure product was obtained in higher yields and in less

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.

New small molecule inhibitors of histone methyl transferase DOT1L with a nitrile as a non-traditional replacement for heavy halogen atoms

A number of new nucleoside derivatives are disclosed as inhibitors of DOT1L activity. SARs established that DOT1L inhibition could be achieved through incorporation of polar groups and small heterocycles at the 5-position (5, 6, 12) or by the application of alternative nitrogenous bases (18). Based on these results, CN-SAH (19) was identified as a potent and selective inhibitor of DOT1L activity where the polar 5-nitrile group was shown by crystallography to bind in the hydrophobic pocket of DOT1L. In addition, we show that a polar nitrile group can be used as a non-traditional replacement for heavy halogen atoms.

Selectivity between N-1 and N-7 nucleosides: Regioselective synthesis of BMK-Y101, a potent cdk7 and 9 inhibitor

BMK-Y101 is a new pyrrolo[2,3-d]pyrimidine-based potent cdk7 and 9 inhibitor, which is characterized by an intriguing structural feature of N-1 nucleoside, departing from previously reported N-7 nucleoside Cdk inhibitor, xylocydine. Though N-1 nucleosides have appeared in the literature, they have often been considered as kinetic products and thus intermediates of N-7 glycosylation. In the course of the synthetic studies of xylocydine derivatives, we have developed a highly regioselective method to obtain the N-1 nucleoside. The origin of the selectivity is apparently based on the reactivity of the silylated nucleobase and the stability of the resulting N-1 nucleoside. The choice of BSA as a silylating agent was critical in securing the N-1 nucleoside, BMK-Y101. On the other hand, proper selection of reaction conditions promoting transglycosylation provides an efficient route to N-7 nucleosides.

CDK-INHIBITING PYRROLOPYRIMIDINONE CARBOXAMIDE DERIVATIVE OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, AND PHARMACEUTICAL COMPOSITION CONTAINING SAME AS ACTIVE INGREDIENT FOR PREVENTING OR TREATING LIVER CELL CANCER

The present invention relates to a CDK-inhibiting pyrrolopyrimidinone carboxamide derivative or a pharmaceutically acceptable salt thereof, and a pharmaceutical composition containing same as an active ingredient for preventing or treating liver cell canc

CDK-INHIBITING PYRROLOPYRIMIDINONE CARBOXAMIDE DERIVATIVE OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, AND PHARMACEUTICAL COMPOSITION CONTAINING THE SAME AS ACTIVE INGREDIENT FOR PREVENTING OR TREATING HEPATOCELLULAR CARCINOMA

The present invention relates to a CDK-inhibiting pyrrolopyrimidinone carboxamide derivative or a pharmaceutically acceptable salt thereof, and a pharmaceutical composition containing same as an active ingredient for preventing or treating liver cell canc

Nitrile reductase from Geobacillus kaustophilus: A potential catalyst for a new nitrile biotransformation reaction

The cloning, expression and characterization of a nitrile reductase (NRed) from the thermophile Geobacillus kaustophilus is reported. The enzyme shows a 12-fold increase in activity in response to a temperature change from 25 °C to 65 °C. The substrate scope regarding its biocatalytic applicability was investigated by testing a range of common nitriles. The narrow substrate range observed for the wild-type enzyme prompted the rational design of GkNRed active site mutants based on a previously published homology model from Bacillus subtilis. The activities of the mutants and the wild-type enzyme were investigated in their structure-function relationship regarding the natural substrate 7-cyano-7-deazaguanine (preQ0) as well as a range of synthesized preQ0-like substrate structures. A distinct dependence of the wild-type enzyme activity on specific structural modifications of the natural substrate was observed. Two non-natural nitriles derived from preQ 0 could be reduced to their corresponding amino compounds. Copyright