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271-70-5,MFCD08234403
Catalog No.:AA0034BJ

271-70-5 | 7H-Pyrrolo[2,3-d]pyrimidine

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100mg
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250mg
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1g
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$12.00   $8.00
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5g
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  • Technical Information
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Technical Information
Catalog Number:
AA0034BJ
Chemical Name:
7H-Pyrrolo[2,3-d]pyrimidine
CAS Number:
271-70-5
Molecular Formula:
C6H5N3
Molecular Weight:
119.1240
MDL Number:
MFCD08234403
SMILES:
c1ncc2c(n1)[nH]cc2
NSC Number:
94210
Properties
Properties
 
BP:
288.3°C at 760 mmHg  
Form:
Solid  
MP:
133 °C  
Storage:
Inert atmosphere;Room Temperature;  

Computed Properties
 
Complexity:
105  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
9  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
1  
XLogP3:
0.7  

Literature

Title: Pyrrolo[2,3-d]pyrimidines active as Btk inhibitors.

Journal: Expert opinion on therapeutic patents 20171201

Title: Targeting conserved water molecules: design of 4-aryl-5-cyanopyrrolo[2,3-d]pyrimidine Hsp90 inhibitors using fragment-based screening and structure-based optimization.

Journal: Bioorganic & medicinal chemistry 20121115

Title: Identification and synthesis of substituted pyrrolo[2,3-d]pyrimidines as novel firefly luciferase inhibitors.

Journal: Bioorganic & medicinal chemistry 20120915

Title: Solid-phase synthesis of tetrasubstituted pyrrolo[2,3-d]pyrimidines.

Journal: Organic & biomolecular chemistry 20120607

Title: N⁴-(3-Bromophenyl)-7-(substituted benzyl) pyrrolo[2,3-d]pyrimidines as potent multiple receptor tyrosine kinase inhibitors: design, synthesis, and in vivo evaluation.

Journal: Bioorganic & medicinal chemistry 20120401

Title: First total synthesis of a naturally occurring iodinated 5'-deoxyxylofuranosyl marine nucleoside.

Journal: Marine drugs 20120401

Title: Pyrrolo[3,2-d]pyrimidine derivatives as type II kinase insert domain receptor (KDR) inhibitors: CoMFA and CoMSIA studies.

Journal: International journal of molecular sciences 20120101

Title: Nuclear targeting of IGF-1 receptor in orbital fibroblasts from Graves' disease: apparent role of ADAM17.

Journal: PloS one 20120101

Title: Synthesis of new pyrroles of potential anti-inflammatory activity.

Journal: Archiv der Pharmazie 20111201

Title: Synthesis and anti-HIV-1 activity of 4-substituted-7-(2'-deoxy-2'-fluoro-4'-azido-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine analogues.

Journal: Bioorganic & medicinal chemistry letters 20111115

Title: 2-Amino-4-methyl-5-phenylethyl substituted-7-N-benzyl-pyrrolo[2,3-d]pyrimidines as novel antitumor antimitotic agents that also reverse tumor resistance.

Journal: Bioorganic & medicinal chemistry 20110715

Title: New condensed pyrroles of potential biological interest syntheses and structure-activity relationship studies.

Journal: European journal of medicinal chemistry 20110701

Title: Insulin-like growth factor-I receptor inhibition by specific tyrosine kinase inhibitor NVP-AEW541 in endometrioid and serous papillary endometrial cancer cell lines.

Journal: Gynecologic oncology 20110501

Title: Discovery of pyrrolo[2,3-d]pyrimidin-4-ones as corticotropin-releasing factor 1 receptor antagonists with a carbonyl-based hydrogen bonding acceptor.

Journal: Bioorganic & medicinal chemistry letters 20110415

Title: Synthesis and discovery of water-soluble microtubule targeting agents that bind to the colchicine site on tubulin and circumvent Pgp mediated resistance.

Journal: Journal of medicinal chemistry 20101125

Title: Synthesis of new pyrrolo[2,3-d]pyrimidine derivatives as antibacterial and antifungal agents.

Journal: European journal of medicinal chemistry 20101101

Title: Synthesis of novel pyrrole and pyrrolo[2,3-d]pyrimidine derivatives bearing sulfonamide moiety for evaluation as anticancer and radiosensitizing agents.

Journal: Bioorganic & medicinal chemistry letters 20101101

Title: Targeting the proton-coupled folate transporter for selective delivery of 6-substituted pyrrolo[2,3-d]pyrimidine antifolate inhibitors of de novo purine biosynthesis in the chemotherapy of solid tumors.

Journal: Molecular pharmacology 20101001

Title: Toward pyrrolo[2,3-d]pyrimidine scaffolds.

Journal: The Journal of organic chemistry 20100806

Title: Synthesis and biological evaluation of some thio containing pyrrolo [2,3-d]pyrimidine derivatives for their anti-inflammatory and anti-microbial activities.

Journal: European journal of medicinal chemistry 20100701

Title: 7-(5-Methyl-sulfanyl-β-d-erythrofuran-osyl)-7H-pyrrolo-[2,3-d]pyrimidin-4-amine monohydrate (MT-tubercidin·H(2)O).

Journal: Acta crystallographica. Section E, Structure reports online 20100701

Title: Synthesis of new pyrrolo[2,3-d]pyrimidine derivatives and evaluation of their activities against human colon cancer cell lines.

Journal: European journal of medicinal chemistry 20100401

Title: 5-Chloro-N-[2-(1H-imidazol-4-yl)eth-yl]-N-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine.

Journal: Acta crystallographica. Section E, Structure reports online 20100101

Title: Synthesis of pyrrolo[2,3-d]pyrimidine derivatives and their antiproliferative activity against melanoma cell line.

Journal: Bioorganic & medicinal chemistry letters 20091201

Title: Novel 7H-pyrrolo[2,3-d]pyrimidine derivatives as potent and orally active STAT6 inhibitors.

Journal: Bioorganic & medicinal chemistry 20091001

Title: Design, synthesis and dopamine D4 receptor binding activities of new N-heteroaromatic 5/6-ring Mannich bases.

Journal: Bioorganic & medicinal chemistry 20090701

Title: Synthesis and antiviral evaluation of 2'-C-methyl analogues of 5-alkynyl- and 6-alkylfurano- and pyrrolo[2,3-d]pyrimidine ribonucleosides.

Journal: Nucleosides, nucleotides & nucleic acids 20090501

Title: 8-Aza-7-deazaguanine nucleosides and oligonucleotides with octadiynyl side chains: synthesis, functionalization by the azide-alkyne 'click' reaction and nucleobase specific fluorescence quenching of coumarin dye conjugates.

Journal: Organic & biomolecular chemistry 20090407

Title: Electronic and steric effects on the mechanism of the inverse electron demand Diels-Alder reaction of 2-aminopyrroles with 1,3,5-triazines: identification of five intermediates by 1H, 13C, 15N, and 19F NMR spectroscopy.

Journal: The Journal of organic chemistry 20090102

Title: Novel antitumor acetamide, pyrrole, pyrrolopyrimidine, thiocyanate, hydrazone, pyrazole, isothiocyanate and thiophene derivatives containing a biologically active pyrazole moiety.

Journal: Arzneimittel-Forschung 20090101

Title: Synthesis and discovery of high affinity folate receptor-specific glycinamide ribonucleotide formyltransferase inhibitors with antitumor activity.

Journal: Journal of medicinal chemistry 20080828

Title: The effect of 5-alkyl modification on the biological activity of pyrrolo[2,3-d]pyrimidine containing classical and nonclassical antifolates as inhibitors of dihydrofolate reductase and as antitumor and/or antiopportunistic infection agents.

Journal: Journal of medicinal chemistry 20080814

Title: Xanthine oxidase-activated prodrugs of thymidine phosphorylase inhibitors.

Journal: European journal of medicinal chemistry 20080601

Title: Design, synthesis and biological evaluation of substituted pyrrolo[2,3-d]pyrimidines as multiple receptor tyrosine kinase inhibitors and antiangiogenic agents.

Journal: Bioorganic & medicinal chemistry 20080515

Title: The insulin-like growth factor-I receptor inhibitor NVP-AEW541 provokes cell cycle arrest and apoptosis in multiple myeloma cells.

Journal: British journal of haematology 20080501

Title: A CoMSIA study on the adenosine kinase inhibition of pyrrolo[2,3-d]pyrimidine nucleoside analogues.

Journal: Bioorganic & medicinal chemistry 20080501

Title: Antagonists of the human adenosine A2A receptor. Part 3: Design and synthesis of pyrazolo[3,4-d]pyrimidines, pyrrolo[2,3-d]pyrimidines and 6-arylpurines.

Journal: Bioorganic & medicinal chemistry letters 20080501

Title: Molecular modeling study and synthesis of novel pyrrolo[2,3-d]pyrimidines and pyrrolotriazolopyrimidines of expected antitumor and radioprotective activities.

Journal: Bioorganic & medicinal chemistry 20080301

Title: Biochemical and biological properties of 5-bromotubercidin: differential effects on cellular DNA-directed and viral RNA-directed RNA synthesis.

Journal: Bioorganic & medicinal chemistry 20080201

Title: [New furano- and pyrrolo[2,3-d]pyrimidine nucleosides and their 5'-triphosphates: synthesis and biological properties].

Journal: Bioorganicheskaia khimiia 20080101

Title: Inhibition of epidermal growth factor receptor and vascular endothelial growth factor receptor phosphorylation on tumor-associated endothelial cells leads to treatment of orthotopic human colon cancer in nude mice.

Journal: Neoplasia (New York, N.Y.) 20071201

Title: Role of focal adhesion kinase in human cancer: a potential target for drug discovery.

Journal: Anti-cancer agents in medicinal chemistry 20071101

Title: Classical anticytokinins do not interact with cytokinin receptors but inhibit cyclin-dependent kinases.

Journal: The Journal of biological chemistry 20070511

Title: Synthesis of pyrrolo[2,3-d]pyrimidine nucleoside derivatives as potential anti-HCV agents.

Journal: Bioorganic chemistry 20070201

Title: Furano- and pyrrolo [2,3-d] pyrimidine nucleosides and their 5'-O-triphospates: synthesis and enzymatic activity.

Journal: Nucleosides, nucleotides & nucleic acids 20070101

Title: The synthesis and properties of tricyclic analogues of S6-methylthioguanine and O6-methylguanine.

Journal: Nucleosides, nucleotides & nucleic acids 20070101

Title: The syntheses and properties of tricyclic pyrrolo[2,3-d]pyrimidine analogues of S6-methylthioguanine and O6-methylguanine.

Journal: Organic & biomolecular chemistry 20060507

Title: Cell cycle arrest and apoptotic induction in LNCaP cells by MCS-C2, novel cyclin-dependent kinase inhibitor, through p53/p21WAF1/CIP1 pathway.

Journal: Cancer science 20060501

Title: Progress in 7-deazapurine - pyrrolo[2,3-d]pyrimidine - ribonucleoside synthesis.

Journal: Current topics in medicinal chemistry 20060101

Title: Novel antitumor and radioprotective sulfonamides containing pyrrolo [2,3-d]pyrimidines.

Journal: Arzneimittel-Forschung 20060101

Title: Synthesis of N-{4-[(2,4-diamino-5-methyl-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl)thio]benzoyl}-L-glutamic acid and N-{4-[(2-amino-4-oxo-5-methyl-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl)thio]benzoyl}-L-glutamic acid as dual inhibitors of dihydrofolate reductase and thymidylate synthase and as potential antitumor agents.

Journal: Journal of medicinal chemistry 20051117

Title: Synthesis and antimicrobial screening of some fused heterocyclic pyrroles.

Journal: Acta pharmaceutica (Zagreb, Croatia) 20050901

Title: Synthesis and biological evaluation of acyclic 3-[(2-hydroxyethoxy)methyl] analogues of antiviral furo- and pyrrolo[2,3-d]pyrimidine nucleosides.

Journal: Journal of medicinal chemistry 20050714

Title: Synthesis and properties of 7-substituted 7-deazapurine (pyrrolo[2,3-d]pyrimidine) 2'-deoxyribonucleosides.

Journal: Current protocols in nucleic acid chemistry 20050701

Title: Role of insulin-like growth factor 1 receptor signalling in cancer.

Journal: British journal of cancer 20050620

Title: Induction of apoptosis in human leukemia cells by MCS-C2 via caspase-dependent Bid cleavage and cytochrome c release.

Journal: Cancer letters 20050608

Title: Synthesis of classical, three-carbon-bridged 5-substituted furo[2,3-d]pyrimidine and 6-substituted pyrrolo[2,3-d]pyrimidine analogues as antifolates.

Journal: Journal of medicinal chemistry 20041230

Title: Synthesis and enzymatic evaluation of xanthine oxidase-activated prodrugs based on inhibitors of thymidine phosphorylase.

Journal: Bioorganic & medicinal chemistry letters 20041101

Title: AEE788: a dual family epidermal growth factor receptor/ErbB2 and vascular endothelial growth factor receptor tyrosine kinase inhibitor with antitumor and antiangiogenic activity.

Journal: Cancer research 20040715

Title: A TOPS-MODE approach to predict adenosine kinase inhibition.

Journal: Bioorganic & medicinal chemistry letters 20040621

Title: In vivo antitumor activity of NVP-AEW541-A novel, potent, and selective inhibitor of the IGF-IR kinase.

Journal: Cancer cell 20040301

Title: A new and efficient synthesis of pyrrolo[2,3-d]pyrimidine anticancer agents: Alimta (LY231514, MTA), homo-Alimta, TNP-351, and some aryl 5-substituted pyrrolo[2,3-d]pyrimidines.

Journal: The Journal of organic chemistry 20031226

Title: Synthesis and evaluation of optically pure dioxolanes as inhibitors of hepatitis C virus RNA replication.

Journal: Bioorganic & medicinal chemistry letters 20031215

Title: Novel synthesis and antifungal activity of pyrrole and pyrrolo[2,3-d]pyrimidine derivatives containing sulfonamido moieties.

Journal: Farmaco (Societa chimica italiana : 1989) 20020801

Title: N(7)-substituted-5-aryl-pyrrolo[2,3-d]pyrimidines represent a versatile class of potent inhibitors of the tyrosine kinase c-Src.

Journal: Mini reviews in medicinal chemistry 20020601

Title: QSAR study on adenosine kinase inhibition of pyrrolo[2,3-d]pyrimidine nucleoside analogues using the hansch approach.

Journal: Bioorganic & medicinal chemistry letters 20020325

Title: Multi-targeted antifolates aimed at avoiding drug resistance form covalent closed inhibitory complexes with human and Escherichia coli thymidylate synthases.

Journal: Journal of molecular biology 20011102

Title: Tyrosine kinase inhibitors: from rational design to clinical trials.

Journal: Medicinal research reviews 20011101

Title: Pyrrolo[2,3-d]pyrimidine thymidylate synthase inhibitors: design and synthesis of one-carbon bridge derivatives.

Journal: Chemical & pharmaceutical bulletin 20011001

Title: Chemical modification of aryl-1,2,3,6-tetrahydropyridinopyrimidine derivative to discover corticotropin-releasing factor(1) receptor antagonists: aryl-1,2,3,6-tetrahydropyridino-purine, -3H-1,2,3-triazolo[4,5-d)pyrimidine, -purin-8-one, and -7H-pyrrolo[2,3-d]pyrimidine derivatives.

Journal: Bioorganic & medicinal chemistry 20010501

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