1320288-30-9

Usage

Uses

Used in Pharmaceutical Industry:
2,4-dichloro-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazoline is used as a potential pharmaceutical agent for its diverse activities, including anticancer, antihypertensive, and antihistaminic properties. Its complex structure and the presence of the pyrrolidin-1-yl group suggest that it may interact with muscarinic receptors, which could be beneficial in the regulation of various physiological functions.
Used in Drug Discovery:
In the field of drug discovery, 2,4-dichloro-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazoline is used as a compound of interest for its potential to be developed into new medications. Its quinazoline backbone and functional groups may offer unique opportunities for the treatment of various diseases and conditions, pending further research and development.
Used in Medicinal Chemistry:
2,4-dichloro-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazoline is utilized in medicinal chemistry as a compound with potential for the development of new therapeutic agents. Its structural features and pharmacological activities make it a promising candidate for the design and synthesis of novel drugs targeting specific biological pathways and receptors.

Upstream product

• 1320288-23-0 methyl 5-methoxy-2-nitro-4-[3-(pyrrolidin-1-yl)propoxy]benzoate 
• 1320288-24-1 methyl 2-amino-5-methoxy-4-[3-(pyrrolidin-1-yl)propoxy]benzoate 
• 1320288-27-4 C₁₇H₂₅N₃O₅ 
• 1320288-29-6 6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)-1H-quinazoline-2,4-dione 
• 3943-74-6 4-hydroxy-3-methoxybenzoic acid methyl ester 
• 111627-40-8 methyl 4-(3-chloropropoxy)-3-methoxybenzoate 
• 214470-57-2 methyl 4-(3-chloropropoxy)-5-methoxy-2-nitrobenzoate 
• 760155-54-2 2-amino-5-methoxy-4-(3-pyrrolidin-1-ylpropoxy)benzamide 
• 199327-73-6 5-methoxy-2-nitro4-(3-(pyrrolidin-1-yl)propoxy)benzamide 
• 745776-25-4 5-methoxy-2-nitro-4-(3-pyrrolidin-1-ylpropoxy)benzoic acid 
• 343308-49-6 methyl 4-(3-bromopropoxy)-5-methoxy-2-nitrobenzoate 
• 27883-60-9 4-hydroxy-5-methoxy-2-nitrobenzoic acid methyl ester 
• 61032-41-5 methyl 4-(benzyloxy)-5-methoxy-2-nitrobenzoate 

Downstream Products

• 1320288-52-5 2-(4-cyclohexyl-1,4-diazepan-1-yl)-N-(1-isopropylpiperidin-4-yl)-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazolin-4-amine 
• 1320288-54-7 2-(4-(cyclohexylmethyl)-1,4-diazepan-1-yl)-N-(1-isopropylpiperidin-4-yl)-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazolin-4-amine 
• 1320288-56-9 N-(1-isopropylpiperidin-4-yl)-6-methoxy-2-(4-phenyl-1,4-diazepan-1-yl)-7-(3-(pyrrolidin-1-yl)propoxy)quinazolin-4-amine 
• 1320288-58-1 2-(4-benzyl-1,4-diazepan-1-yl)-N-(1-isopropylpiperidin-4-yl)-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazolin-4-amine 
• 1481677-78-4 UNC0642 

Relevant academic research and scientific papers

Discovery of Reversible DNA Methyltransferase and Lysine Methyltransferase G9a Inhibitors with Antitumoral in Vivo Efficacy

Using knowledge- and structure-based approaches, we designed and synthesized reversible chemical probes that simultaneously inhibit the activity of two epigenetic targets, histone 3 lysine 9 methyltransferase (G9a) and DNA methyltransferases (DNMT), at nanomolar ranges. Enzymatic competition assays confirmed our design strategy: substrate competitive inhibitors. Next, an initial exploration around our hit 11 was pursued to identify an adequate tool compound for in vivo testing. In vitro treatment of different hematological neoplasia cell lines led to the identification of molecules with clear antiproliferative efficacies (GI50 values in the nanomolar range). On the basis of epigenetic functional cellular responses (levels of lysine 9 methylation and 5-methylcytosine), an acceptable therapeutic window (around 1 log unit) and a suitable pharmacokinetic profile, 12 was selected for in vivo proof-of-concept (Nat. Commun. 2017, 8, 15424). Herein, 12 achieved a significant in vivo efficacy: 70% overall tumor growth inhibition of a human acute myeloid leukemia (AML) xenograft in a mouse model.

Discovery of an in vivo chemical probe of the lysine methyltransferases G9a and GLP

Among epigenetic "writers", "readers", and "erasers", the lysine methyltransferases G9a and GLP, which catalyze mono- and dimethylation of histone H3 lysine 9 (H3K9me2) and nonhistone proteins, have been implicated in a variety of human diseases. A "toolk

Optimization of cellular activity of G9a inhibitors 7-aminoalkoxy- quinazolines

Protein lysine methyltransferase G9a plays key roles in the transcriptional repression of a variety of genes via dimethylation of lysine 9 on histone H3 (H3K9me2) of chromatin as well as dimethylation of nonhistone proteins including tumor suppressor p53. We previously reported the discovery of UNC0321 (3), the most potent G9a inhibitor to date, via structure-based design and structure-activity relationship (SAR) exploration of the quinazoline scaffold represented by BIX01294 (1). Despite its very high in vitro potency, compound 3 lacks sufficient cellular potency. The design and synthesis of several generations of new analogues aimed at improving cell membrane permeability while maintaining high in vitro potency resulted in the discovery of a number of novel G9a inhibitors such as UNC0646 (6) and UNC0631 (7) with excellent potency in a variety of cell lines and excellent separation of functional potency versus cell toxicity. The design, synthesis, and cellular SAR of these potent G9a inhibitors are described.