2227-98-7

Basic information

• Product Name: 5H-Pyrrolo[3,2-d]pyrimidin-4-amine (9CI)
• Synonyms: 5H-Pyrrolo[3,2-d]pyrimidin-4-amine (9CI);4-Aminopyrrolo[3,2-d]pyrimidine;1H-pyrrolo[3,2-d]pyriMidin-4-aMine;4-AMino-5H-pyrrolo[3,2-d]pyriMidine;4-AMino-5H-pyrrolo[3,2-d]...
• CAS NO: 2227-98-7
• Molecular Formula: C₆H₆N₄
• Molecular Weight: 134.13864
• EINECS: 1533716-785-6
• Product Categories: PYRIMIDINE;Heterocycle-Pyrimidine series
• Mol File: 2227-98-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 235-237 °C
• Boiling Point: 399.8 °C at 760 mmHg
• Flash Point: 224.4 °C
• Appearance: /
• Density: 1.48 g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 13.84±0.40(Predicted)
• CAS DataBase Reference: 5H-Pyrrolo[3,2-d]pyrimidin-4-amine (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 5H-Pyrrolo[3,2-d]pyrimidin-4-amine (9CI)(2227-98-7)
• EPA Substance Registry System: 5H-Pyrrolo[3,2-d]pyrimidin-4-amine (9CI)(2227-98-7)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 2227-98-7(Hazardous Substances Data)

Usage

General Description

5H-Pyrrolo[3,2-d]pyrimidin-4-amine (9CI) is a chemical compound with a pyrrolopyrimidine core structure. It is also known as 4-Amino-5H-pyrrolo[3,2-d]pyrimidine and has the molecular formula C6H6N4. 5H-Pyrrolo[3,2-d]pyrimidin-4-amine (9CI) is of interest in medicinal chemistry and drug discovery due to its potential biological activities. It has been investigated as a potential inhibitor of kinases and other enzyme targets. Research suggests that derivatives of this compound may have anticancer, antiviral, and antimalarial properties. Additionally, it may also serve as a building block for the synthesis of other biologically active molecules. Overall, 5H-Pyrrolo[3,2-d]pyrimidin-4-amine (9CI) is a versatile chemical with potential applications in various fields.

InChI:InChI:1S/C6H6N4/c7-6-5-4(1-2-8-5)9-3-10-6/h1-3,8H,(H2,7,9,10)

Upstream product

• 5655-01-6 9-deazahypoxanthine 
• 252932-48-2 3-amino-2-ethoxycarbonylpyrrole 
• 2320-75-4 ethyl 4-amino-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylate 
• 1335287-29-0 1,4-anhydro-2-deoxy-3,5-O-(di-tert-butylsilylene)-1-(4-N-pivaloylamino-pyrrolo[3,2-d]pyrimidin-7-yl)-4-thio-D-erythro-pento-1-enitol 
• 1335287-28-9 4-pivaloylamino-7-iodo-3H,5H-pyrrolo[3,2-d]pyrimidine 
• 1335287-27-8 4-pivaloylamino-3H,5H-pyrrolo[3,2-d]pyrimidine 
• 84905-80-6 4-Chloro-5H-pyrrolo[3,2-d]pyrimidine 

Downstream Products

• 653592-04-2 (3R,4S)-1-((4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl)-4-((methylthio)methyl)pyrrolidin-3-ol 
• 653592-04-2 (3S,4R)-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxy-4-(methylthiomethyl)-pyrrolidine 

Relevant articles and documents

COMPOSITIONS AND METHODS FOR THERAPY OF PROSTATE CANCER USING DRUG COMBINATIONS TO TARGET POLYAMINE BIOSYNTHESIS AND RELATED PATHWAYS

Provided are compositions and methods for treating prostate conditions. The methods involve administering to an individual in need thereof a composition that contains i) an inhibitor of methionine salvage pathway in prostate of the individual and ii) a polyamine analogue. The methods are for use in individuals who have been diagnosed with, or are suspected of having or at risk for developing androgen sensitive prostate cancer (AS-CaP), or Castration recurrent CaP (CR-CaP), or benign prostate hyperplasia (BPH). The disclosure includes use of inhibitors of methylthioadenosine phosphorylase (MTAP), and a polyamine analog that upregulates polyamine catabolism by increasing spermidine/spermine Nl -acetyl transferase (SAT1) activity, such as methylthio-DADMe-Immucillin (MTDIA), andl),N(11)-bisethylnorspermine (BENSpm), respectively. Pharmaceutical formulations that contain a combination of the inhibitor of the methionine salvage pathway and a polyamine analogue are included, as are kits that contain such agents.

SALT AND POLYMORPHIC FORMS OF (3R,4S)-L-((4-AMINO-5H-PYRROLO[3,2-D]PYRIMIDIN-7-YL)METHYL)-4(METHYLTHIOMETHYL)PYRODIN-3-OL(MTDIA)

The invention relates to salt forms of (3R,4S)-1-((4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl)-4-(methylthiomethyl)pyrrolidin-3-ol, as well as polymorphic forms of the salts. The invention further relates to processes for preparing the salt forms and to the use of the salt forms in the treatment of diseases and disorders where it is desirable to inhibit 5'-methylthioadenosine phosphorylase (MTAP).

Structure-activity relationships of adenine and deazaadenine derivatives as ligands for adenine receptors, a new purinergic receptor family

Adenine derivatives bearing substituents in the 2-, N6-, 7-, 8-, and/or 9-position and a series of deazapurines were synthesized and investigated in [3H]adenine binding studies at the adenine receptor in rat brain cortical membrane preparations (rAde1R). Steep structure-activity relationships were observed. Substitution in the 8-position (amino, dimethylamino, piperidinyl, piperazinyl) or in the 9-position (2-morpholinoethyl) with basic residues or introduction of polar substituents at the 6-amino function (hydroxy, amino, acetyl) represented the best modifications. Functional evaluation of selected adenine derivatives in adenylate cyclase assays at 1321N1 astrocytoma cells stably expressing the rAde1R showed that all compounds investigated were agonists or partial agonists. A subset of compounds was additionally investigated in binding studies at human embryonic kidney (HEK293) cells, which also express a high-affinity adenine binding site. Structure-affinity relationships at the human cell line were similar to those at the rAde1R, but not identical. In particular, N 6-acetyladenine (25, Ki rat: 2.85 μM; Ki human: 0.515 μM) and 8-aminoadenine (33, Ki rat: 6.51 μM; Ki human: 0.0341 μM) were much more potent at the human as compared to the rat binding site. The new AdeR ligands may serve as lead structures and contribute to the elucidation of the functions of the adenine receptor family. 2009 American Chemical Society.