330792-72-8

Basic information

• Product Name: 4-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)cyclohexanone
• CAS NO: 330792-72-8
• Molecular Formula: C₁₁H₁₂IN₅O
• Molecular Weight: 357.1503
• Mol File: 330792-72-8.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 552.657°C at 760 mmHg
• Flash Point: 288.037°C
• Density: 2.221g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.888
• CAS DataBase Reference: 4-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)cyclohexanone(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)cyclohexanone(330792-72-8)
• EPA Substance Registry System: 4-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)cyclohexanone(330792-72-8)

Safety Data

• Hazardous Substances Data: 330792-72-8(Hazardous Substances Data)

Upstream product

• 22428-87-1 4,4-ethylenedioxycyclohexan-1-ol 
• 163622-50-2 4-amino-5-iodo-7H-pyrrolo[2,3‐d]pyrimidine 
• 151266-23-8 4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidine 
• 2380-63-4 4-Aminopyrazolo<3,4-d>pyrimidin 
• 330792-61-5 3-iodo-1-(1,4-dioxaspiro[4.5]decan-8-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine 

Downstream Products

• 330792-74-0 3-iodo-1-((trans)-4-(4-methylpiperazin-1-yl)cyclohexyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 330792-73-9 3-iodo-1-((cis)-4-(4-methylpiperazin-1-yl)cyclohexyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 1603845-21-1 tert-butyl 4-(4-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)cyclohexyl)piperazine-1-carboxylate 
• 1603845-23-3 tert-butyl 4-(4-(4-amino-3-(4-fluoro-3-nitrophenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)cyclohexyl)piperazine-1-carboxylate 
• 1603845-24-4 tert-butyl 4-(4-(4-amino-3-(3-nitro-4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)cyclohexyl)piperazine-1-carboxylate 
• 1603845-27-7 tert-butyl 4-(4-(4-(bis(tert-butoxycarbonyl)amino)-3-(3-nitro-4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)cyclohexyl)piperazine-1-carboxylate 
• 1603845-28-8 tert-butyl 4-(4-(3-(3-amino-4-phenoxyphenyl)-4-(bis(tert-butoxycarbonyl)amino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)cyclohexyl)piperazine-1-carboxylate 
• 1603845-29-9 N-(5-(4-amino-1-(4-(piperazin-1-yl)cyclohexyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-2-phenoxyphenyl)acrylamide 
• 1603845-46-0 tert-butyl 4-(4-(4-amino-3-(3-methoxy-4-(1-methyl-1H-indole-2-carboxamido)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)cyclohexyl)piperazine-1-carboxylate 
• 1603845-47-1 tert-butyl (2-(4-(4-(4-amino-3-(3-methoxy-4-(1-methyl-1H-indole-2-carboxamido)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)cyclohexyl)piperazin-1-yl)ethyl)carbamate 
• 330789-03-2 N-(4-(4-amino-1-((cis)-4-(4-methylpiperazin-1-yl)cyclohexyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-2-methoxyphenyl)-1-methyl-1H-indole-2-carboxamide 
• 330789-03-2 A-420983 
• 330786-13-5 4-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]cyclohexan-1-one 
• 1603845-32-4 TX₁-85-1 

Relevant articles and documents

COMPOUNDS FOR TREATING OR INHIBITING RECURRENCE OF ACUTE MYELOID LEUKEMIA

Provided herein are compounds for treating acute myeloid leukemia or inhibiting recurrence of acute myeloid leukemia and for inhibiting growth of and/or killing leukemic stem cells.

From Lead to Drug Candidate: Optimization of 3-(Phenylethynyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine Derivatives as Agents for the Treatment of Triple Negative Breast Cancer

Herein we report the sophisticated process of structural optimization toward a previously disclosed Src inhibitor, compound 1, which showed high potency in the treatment of triple negative breast cancer (TNBC) both in vitro and in vivo but had considerable toxicity. A series of 3-(phenylethynyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine derivatives were synthesized. In vitro cell-based phenotypic screening together with in vivo assays and structure-activity relationship (SAR) studies finally led to the discovery of N-(3-((4-amino-1-(trans-4-hydroxycyclohexyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl)ethynyl)-4-methylphenyl)-4-methyl-3-(trifluoromethyl)benzamide (13an). 13an is a multikinase inhibitor, which potently inhibited Src (IC50 = 0.003 μM), KDR (IC50 = 0.032 μM), and several kinases involved in the MAPK signal transduction. This compound showed potent anti-TNBC activities both in vitro and in vivo, and good pharmacokinetic properties and low toxicity. Mechanisms of action of anti-TNBC were also investigated. Collectively, the data obtained in this study indicate that 13an could be a promising drug candidate for the treatment of TNBC and hence merits further studies.

AGENT FOR TREATING OR CONTROLLING RECURRENCE OF ACUTE MYELOGENOUS LEUKEMIA

This invention relates to an agent for treating or inhibiting recurrence of acute myeloid leukemia and an agent for inhibiting growth of leukemia stem cells comprising a compound represented by formula (I) or a salt thereof: wherein Ar1 and Ar