113942-32-8

Basic information

• Product Name: 3-(2-chloroethyl)-4-oxo-3H-imidazo(5,1-d)-1,2,3,5-tetrazine-8-carboxylic acid
• Synonyms: 3-(2-chloroethyl)-4-oxo-3H-imidazo(5,1-d)-1,2,3,5-tetrazine-8-carboxylic acid
• CAS NO: 113942-32-8
• Molecular Formula: C₇H₆ClN₅O₃
• Molecular Weight: 243.61
• Mol File: 113942-32-8.mol

Chemical Properties

• Boiling Point: 521.6°Cat760mmHg
• Flash Point: 269.2°C
• Appearance: /
• Density: 1.94g/cm³
• Vapor Pressure: 1.05E-11mmHg at 25°C
• Refractive Index: 1.808
• CAS DataBase Reference: 3-(2-chloroethyl)-4-oxo-3H-imidazo(5,1-d)-1,2,3,5-tetrazine-8-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2-chloroethyl)-4-oxo-3H-imidazo(5,1-d)-1,2,3,5-tetrazine-8-carboxylic acid(113942-32-8)
• EPA Substance Registry System: 3-(2-chloroethyl)-4-oxo-3H-imidazo(5,1-d)-1,2,3,5-tetrazine-8-carboxylic acid(113942-32-8)

Safety Data

• Hazardous Substances Data: 113942-32-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H6ClN5O3/c8-1-2-13-7(16)12-3-9-4(6(14)15)5(12)10-11-13/h3H,1-2H2,(H,14,15)

Upstream product

• 85622-95-3 mitozolomide 
• 113942-31-7 benzyl 3-(2-chloroethyl)-3H-4-oxoimidazo<5,1-d>-1,2,3,5-tetrazine-8-carboxylate 

Downstream Products

• 113942-38-4 3-(2-Chloro-ethyl)-4-oxo-3,4-dihydro-imidazo[5,1-d][1,2,3,5]tetrazine-8-carboxylic acid N'-(2,4-difluoro-phenyl)-hydrazide 
• 113942-41-9 C₁₄H₁₃ClN₈O₃ 
• 113942-37-3 3-(2-Chloro-ethyl)-4-oxo-3,4-dihydro-imidazo[5,1-d][1,2,3,5]tetrazine-8-carboxylic acid N'-phenyl-hydrazide 
• 113942-34-0 3-(2-Chloro-ethyl)-4-oxo-3,4-dihydro-imidazo[5,1-d][1,2,3,5]tetrazine-8-carboxylic acid benzyloxy-amide 
• 90521-13-4 3-(2-Chloro-ethyl)-4-oxo-3,4-dihydro-imidazo[5,1-d][1,2,3,5]tetrazine-8-carboxylic acid phenylamide 
• 113942-53-3 3-(2-Chloro-ethyl)-4-oxo-3,4-dihydro-imidazo[5,1-d][1,2,3,5]tetrazine-8-carboxylic acid cyclohexylamide 
• 85623-00-3 3-(2-chloroethyl)-N,N-dimethyl-4-oxo-3,4-dihydroimidazo<5,1-d>-1,2,3,5-tetrazine-8-carboxamide (DCMCIT) 
• 85622-96-4 3-(2-chloroethyl)-N-methyl-4-oxoimidazo<5,1-d>-1,2,3,5-tetrazine-8-carboxamide 
• 473988-50-0 2-(allyloxy)carbonyl-7-phenoxyacetamido-3-cephem-3-methyl 3-(2-chloroethyl)-4-oxoimidazo[5,1-d][1,2,3,5]tetrazin-8-carboxylate 
• 473988-42-0 2-(allyloxy)carbonyl-7-phenylacetamido-3-cephem-3-methyl 3-(2-chloroethyl)-4-oxo-imidazo[5,1-d][1,2,3,5]tetrazin-8-carboxylate 

Relevant articles and documents

Hydroxamic Acids Immobilized on Resins (HAIRs): Synthesis of Dual-Targeting HDAC Inhibitors and HDAC Degraders (PROTACs)

Inhibition of more than one cancer-related pathway by multi-target agents is an emerging approach in modern anticancer drug discovery. Here, based on the well-established synergy between histone deacetylase inhibitors (HDACi) and alkylating agents, we present the discovery of a series of alkylating HDACi using a pharmacophore-linking strategy. For the parallel synthesis of the target compounds, we developed an efficient solid-phase-supported protocol using hydroxamic acids immobilized on resins (HAIRs) as stable and versatile building blocks for the preparation of functionalized HDACi. The most promising compound, 3 n, was significantly more active in apoptosis induction, activation of caspase 3/7, and formation of DNA damage (γ-H2AX) than the sum of the activities of either active principle alone. Furthermore, to demonstrate the utility of our preloaded resins, the HAIR approach was successfully extended to the synthesis of a proof-of-concept proteolysis-targeting chimera (PROTAC), which efficiently degrades histone deacetylases.

Synthesis and antibacterial activity of dual-action agents of a β-lactam antibiotic with cytotoxic agent mitozolomide or temozolomide

Dual-action agents 5a-f and 12a-f, a β-lactam antibiotic combined with a cytotoxic agent, mitozolomide (Meto) or temozolomide (Temo), were synthesised. The antibacterial activity (MICs) of the dual-action agents has been determined against a panel of bacteria including several β-lactamase producing strains. The tests showed 5a-f active against the non-β-lactamase producing methicillin sensitive Staphylococcus aureus (MSSA) strains, however, little synergistic effect between the β-lactam and the cytotoxic agent was observed. 12a-f demonstrated some synergistic effect against bacteria. 12a, in particular, is active against ampicillin resistant (β-lactamase-producing) strains of Serratia marcescens.

Solid phase synthesis of a mitozolomide-oligonucleotide conjugate using a novel silyl-linked solid support

A new strategy for automated solid phase synthesis of an oligonucleotide conjugate of the base sensitive anti-cancer agent mitozolomide is described. Fully protected oligonucleotides were selected as base sensitive model sequences and were synthesized in

Antitumor Imidazotetrazines. 20. Preparation of the 8-Acid Derivative of Mitozolomide and Its Utility in the Preparation of Active Antitumor Agents

The preparation of 3-(2-chloroethyl)-4-oxo-3H-imidazo-1,2,3,5-tetrazine-8-carboxylic acid, a key derivative of mitozolomide in our exploration of the structure-activity relationships of this class of antitumor agents, is described.The facile conver