59368-16-0

Basic information

• Product Name: 6-(Bromomethyl)-2,4-pteridinediamine
• Synonyms: 2,4-Diamino-6-bromomethylpteridine;6-(Bromomethyl)-2,4-pteridinediamine;6-Bromomethyl-2,4-diaminopteridine;6-(Bromomethyl)pteridine-2,4-diamine;2,4-PteridinediaMine, 6-(broMoMethyl)-;Methotrexate Impurity 13
• CAS NO: 59368-16-0
• Molecular Formula: C₇H₇BrN₆
• Molecular Weight: 255.07468
• EINECS: 1592732-453-0
• Mol File: 59368-16-0.mol

Chemical Properties

• Melting Point: 168-170 °C
• Boiling Point: 520.7 °C at 760 mmHg
• Flash Point: 268.7 °C
• Appearance: /
• Density: 1.954
• Vapor Pressure: 6.08E-11mmHg at 25°C
• Refractive Index: 1.835
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 5.51±0.10(Predicted)
• CAS DataBase Reference: 6-(Bromomethyl)-2,4-pteridinediamine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-(Bromomethyl)-2,4-pteridinediamine(59368-16-0)
• EPA Substance Registry System: 6-(Bromomethyl)-2,4-pteridinediamine(59368-16-0)

Safety Data

• Hazardous Substances Data: 59368-16-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-(Bromomethyl)-2,4-pteridinediamine serves as a key reactant in the synthesis of a variety of pharmaceutical compounds. Its chemical reactivity and structural features make it suitable for the creation of new drug molecules, contributing to the advancement of treatments for various diseases and conditions.
Used in Agrochemical Industry:
In the agrochemical sector, 6-(Bromomethyl)-2,4-pteridinediamine is utilized in the synthesis of compounds that have applications in agriculture, such as pesticides and herbicides. Its role in these syntheses helps to develop more effective and targeted agrochemicals to improve crop protection and yield.
Used in Research and Development:
6-(Bromomethyl)-2,4-pteridinediamine is employed as a reactant in the research and development of innovative drugs and drug delivery systems. Its versatility allows scientists to explore new avenues in drug design, potentially leading to the discovery of more effective and safer medications.
Used as a Building Block in Organic Synthesis:
Recognized for its potential in organic synthesis, 6-(Bromomethyl)-2,4-pteridinediamine is used to construct complex organic molecules. Its bromomethyl group provides a handle for further chemical reactions, facilitating the synthesis of a wide range of organic compounds for various applications.

InChI:InChI=1/C7H7BrN6/c8-1-3-2-11-6-4(12-3)5(9)13-7(10)14-6/h2H,1H2,(H4,9,10,11,13,14)

Upstream product

• 37150-52-0 3-bromoacetonaldoxime 
• 112740-59-7 2-oxo-3-bromopropanal oxime 
• 73978-41-3 2,4-diamino-6-(hydroxymethyl)pteridine hydrochloride 
• 708-74-7 2,4-diamino-6-methylpteridine 
• 113311-25-4 2,4-diamino-6-dibromomethylpteridine 
• 94-36-0 dibenzoyl peroxide 
• 191786-02-4 N-{2-Butyrylamino-6-[(E)-2-(4-ethyl-phenyl)-vinyl]-pteridin-4-yl}-butyramide 
• 191786-04-6 N-(2-Butyrylamino-6-hydroxymethyl-pteridin-4-yl)-butyramide 
• 191786-03-5 N-(2-Butyrylamino-6-formyl-pteridin-4-yl)-butyramide 
• 191786-01-3 β-(2,4-diamino-6-pteridinyl)-p-ethylstyrene 
• 52853-40-4 6-bromomethyl-2,4-diaminopteridine hydrobromide 
• 76145-91-0 2,4-diamino-6-hydroxymethylpteridine hydrobromide 
• 1034-39-5 dibromotriphenylphosphorane 
• 945-24-4 2,4-diamino-6-(hydroxymethyl)pteridine 

Downstream Products

• 136451-01-9 Diethyl-N-<4-<(2,4-diamino-6-pteridinyl)methyl>-N-methylaminobenzoyl>-β-phenylglutamat 
• 136451-04-2 Diethyl-N-<4-<(2,4-diamino-6-pteridinyl)methyl>-N-methylaminobenzoyl>-β-(4-methylphenyl)glutamat 
• 136451-02-0 Diethyl-N-<4-<(2,4-diamino-6-pteridinyl)methyl>-N-methylaminobenzoyl>-β-(4-chlorphenyl)glutamat 
• 136451-03-1 Diethyl-N-<4-<(2,4-diamino-6-pteridinyl)methyl>-N-methylaminobenzoyl>-β-(4-bromphenyl)glutamat 
• 102841-30-5 2-{4-[(2,4-Diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-2-difluoromethyl-pentanedioic acid dimethyl ester 
• 95772-55-7 2-{4-[(2,4-Diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-4-fluoro-pentanedioic acid diisopropyl ester 
• 174654-78-5 6-(3-Chloro-phenylsulfanylmethyl)-pteridine-2,4-diamine 
• 70583-39-0 6-(naphthalen-1-ylamino-methyl)-pteridine-2,4-diamine 
• 57963-46-9 6-(4-chloro-anilinomethyl)-pteridine-2,4-diamine 
• 57963-58-3 6-phenylsulfanylmethyl-pteridine-2,4-diamine 
• 174654-74-1 6-p-Tolylsulfanylmethyl-pteridine-2,4-diamine 

Relevant articles and documents

The structure-based design and synthesis of selective inhibitors of Trypanosoma cruzi dihydrofolate reductase

This paper describes the design and synthesis of potential inhibitors of Trypanosoma cruzi dihydrofolate reductase using a structure-based approach. A model of the structure of the T. cruzi enzyme was compared with the structure of the human enzyme. The differences were used to design modifications of methotrexate to produce compounds which should be selective for the parasite enzyme. The derivatives of methotrexate were synthesised and tested against the enzyme and intact parasites.

PROTEIN DEGRADATION INDUCING TAG AND USAGE THEREOF

Provided are: a protein degradation inducing tag which is a molecule that has affinity with proteases and does not inhibit degradation of a protein by proteases; a protein degradation inducing molecule that is a conjugate of at least one protein degradation inducing tag and at least one protein binding molecule that binds to a protein; and a usage of those.

Cell-Surface Receptor-Ligand Interaction Analysis with Homogeneous Time-Resolved FRET and Metabolic Glycan Engineering: Application to Transmembrane and GPI-Anchored Receptors

Ligand-binding assays are the linchpin of drug discovery and medicinal chemistry. Cell-surface receptors and their ligands have traditionally been characterized by radioligand-binding assays, which have low temporal and spatial resolution and entail safety risks. Here, we report a powerful alternative (GlycoFRET), where terbium-labeled fluorescent reporters are irreversibly attached to receptors by metabolic glycan engineering. For the first time, we show time-resolved fluorescence resonance energy transfer between receptor glycans and fluorescently labeled ligands. We describe GlycoFRET for a GPI-anchored receptor, a G-protein-coupled receptor, and a heterodimeric cytokine receptor in living cells with excellent sensitivity and high signal-to-background ratios. In contrast to previously described methods, GlycoFRET does not require genetic engineering or antibodies to label receptors. Given that all cell-surface receptors are glycosylated, we expect that GlycoFRET can be generalized with applications in chemical biology and biotechnology, such as target engagement, receptor pharmacology, and high-throughput screening.

Pterin–sulfa conjugates as dihydropteroate synthase inhibitors and antibacterial agents

The sulfonamide class of antibiotics has been in continuous use for over 70?years. They are thought to act by directly inhibiting dihydropteroate synthase (DHPS), and also acting as prodrugs that sequester pterin pools by forming dead end pterin–sulfonamide conjugates. In this study, eight pterin–sulfonamide conjugates were synthesized using a novel synthetic strategy and their biochemical and microbiological properties were investigated. The conjugates were shown to competitively inhibit DHPS, and inhibition was enhanced by the presence of pyrophosphate that is crucial to catalysis and is known to promote an ordering of the DHPS active site. The co-crystal structure of Yersinia pestis DHPS bound to one of the more potent conjugates revealed a mode of binding that is similar to that of the enzymatic product analog pteroic acid. The antimicrobial activities of the pterin–sulfonamide conjugates were measured against Escherichia coli in the presence and absence of folate precursors and dependent metabolites. These results show that the conjugates have appreciable antibacterial activity and act by an on target, anti-folate pathway mechanism rather than as simple dead end products.

Bisubstrate analogue inhibitors of 6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase: New design with improved properties

6-Hydroxymethyl-7,8-dihydropterin pyrophosphokinase (HPPK), a key enzyme in the folate biosynthetic pathway, catalyzes the pyrophosphoryl transfer from ATP to 6-hydroxymethyl-7,8-dihydropterin. The enzyme is essential for microorganisms, is absent from humans, and is not the target for any existing antibiotics. Therefore, HPPK is an attractive target for developing novel antimicrobial agents. Previously, we characterized the reaction trajectory of HPPK-catalyzed pyrophosphoryl transfer and synthesized a series of bisubstrate analog inhibitors of the enzyme by linking 6-hydroxymethylpterin to adenosine through 2, 3, or 4 phosphate groups. Here, we report a new generation of bisubstrate analog inhibitors. To improve protein binding and linker properties of such inhibitors, we have replaced the pterin moiety with 7,7-dimethyl-7,8- dihydropterin and the phosphate bridge with a piperidine linked thioether. We have synthesized the new inhibitors, measured their Kd and IC 50 values, determined their crystal structures in complex with HPPK, and established their structure-activity relationship. 6-Carboxylic acid ethyl ester-7,7-dimethyl-7,8-dihydropterin, a novel intermediate that we developed recently for easy derivatization at position 6 of 7,7-dimethyl-7,8- dihydropterin, offers a much high yield for the synthesis of bisubstrate analogs than that of previously established procedure.

LINKED PURINE PTERIN HPPK INHIBITORS USEFUL AS ANTIBACTERIAL AGENTS

The disclosure provides linked purine pterin compounds and analogues thereof that are novel HPPK inhibitors. The HPPK inhibitors described herein are compounds and the pharmaceutically acceptable salts thereof of general Formula I: (I). The variables, e.g. A1 to A3, R1 to R4, L1, L2, B1, and B2 are described herein. Compounds and salts of Formula I bind to HPPK with high affinity and specificity. Pharmaceutical compositions containing an HPPK inhibitor of Formula I and methods of treating a bacterial infection in a patient by providing one or more HPPK inhibitors of Formula I to the patient are also provided. Processes and intermediates useful for preparing compounds of Formula I are also provided. Methods of using the disclosed compounds to guide the development of additional novel anti-bacterial agents are also provided.

Pteridine-sulfonamide conjugates as dual inhibitors of carbonic anhydrases and dihydrofolate reductase with potential antitumor activity

Recent evidences suggest that cancer treatment based on combination of cytostatic and conventional chemostatic therapeutics, which are usually cytotoxic, can provide an improved curative option. On the sequence of our previous work on methotrexate (MTX) derivatives, we have developed and evaluated novel MTX analogues, containing a pteridine moiety conjugated with benzenesulfonamide derivatives, thus endowed with the potential capacity for dual inhibition of dihydrofolate reductase (DHFR) and carbonic anhydrases (CA). These enzymes are often overexpressed in tumors and are involved in two unrelated cellular pathways, important for tumor survival and progression. Their simultaneous inhibition may turn beneficial in terms of enhanced antitumor activity. Herein we report the design and synthesis of several diaminopteridine-benzenesulfonamide and -benzenesulfonate conjugates, differing in the nature and size of the spacer group between the two key moieties. The inhibition studies performed on a set of CAs and DHFR, revealed the activities in the low nanomolar and low micromolar ranges of concentration, respectively. Some inhibitors showed selectivity for the tumor-related CA (isozyme IX). Cell proliferation assays using two tumor cell lines (the non-small cell lung carcinoma, A549, and prostate carcinoma, PC-3) showed activities only in the millimolar range. Nevertheless, this fact points out the need of improving the cell intake properties of these new compounds, since the general inhibitory profiles revealed their potential as anticancer agents.

DIAMINOPTERIDINE DERIVATIVES

The present invention relates novel diaminopteridine derivatives, their compositions and method of treatment comprising the same for use as anti-infectives.

TRIAZOLE DERIVATIVES AS VASOPRESSIN ANTAGONISTS

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