Description

Quinazolines are a big family of heterocyclic compounds with anti-cancer properties.Cytotoxicity assays were performed for all compounds against different cell lines such as Human colon carcinoma (HCT116), Human chronic myeloid leukemia (K562) and Human breast cancer (SKBR3) cell lines using 3-(4,5-Dimethylthiazol-2-yl)-2,5-Diphenyl tetrazolium Bromide (MTT), Trypan blue and Lactose dehydrogenase release assay. The selected compounds were evaluated for their anti-tumor and anti-angiogenic effect on EAC tumor model. The molecular docking studies were drawn using maestro 2D sketcher and energy minimize was compounded by OPLS 2005.

The current study focused on balancing potency and selectivity with metabolic stability through structural modification to the metabolized site on the quinazoline core. The performed extensive structure-activity and structure-property relationship studies on this quinazoline ATM kinase inhibitor in order to identify structural variants with enhanced selectivity and metabolic stability. It shows that, while the C-7-methoxy group is essential for potency, replacing the C-6-methoxy group considerably improves metabolic stability without affecting potency. Promising analogues 20, 27g, and 27n were selected based on in vitro pharmacology and evaluated in murine pharmacokinetic and tolerability studies. Compound 27g possessed significantly improve pharmacokinetics relative to that of 4. Compound 27g was also significantly more selective against other kinases than 4. Therefore, 27g is a good candidate for further development as a potential radiosensitizer.

 

2-Chloro-4-Amino-6,7-Dimethoxyquinazoline(23680-84-4) Specifications

CAS	23680-84-4
CAS Min %	95.0
CAS Max %	100.0
MDL Number	MFCD00051734
InChI Key	HWIIAAVGRHKSOJ-UHFFFAOYSA-N
Chemical Name or Material	2-Chloro-4-amino-6,7-dimethoxyquinazoline
Infrared Spectrum	Authentic
Physical Form	Powder or Chunks
Packaging	Glass bottle
Molecular Formula	C10H10ClN3O2
Molecular Weight (g/mol)	239.66
SMILES	Clc2nc1c(cc(OC)c(OC)c1)c(n2)N
Color	Off-white
Melting Point	262-268°C
Assay	95%

2-Chloro-4-Amino-6,7-Dimethoxyquinazoline(23680-84-4) Safety and Handling

(23680-84-4) Hazard description:

♦ Causes skin irritation

♦ Causes serious eye irritation

♦ May cause respiratory irritation

(23680-84-4) Precautionary statement:

♦ Avoid breathing dust/fume/gas/mist/vapours/spray.

♦ Wash skin thouroughly after handling.

♦ Use only outdoors or in a well-ventilated area.

♦ Wear protective gloves/protective clothing/eye protection/face protection.

♦ Store in a well-ventilated place. Keep container tightly closed.

♦ Dispose of contents/container to an approved waste disposal plant.

WARNING: The information provided on this web site was developed in compliance with European Union (EU) regulations and is correct to the best of our knowledge, information and belief at the date of its publication. The information given is designed only as a guide for safe handling and use. It is not to be considered as either a warranty or quality specification.

2-Chloro-4-Amino-6,7-Dimethoxyquinazoline(23680-84-4) Articles

Synthesis and biological evaluation of novel quinazoline-sulfonamides as anti-cancer agents

A robust economic approach to N-(quinazoline-4-yl)sulfonamides was developed and synthesized different aryl, hetero aryl, alkyl and cyclopropyl sulfonamides in excellent yields.

Bioorganic and Medicinal Chemistry Letters 2017 vol. 27 # 9 p. 1923 – 1928

ROS1 kinase inhibitors for molecular-targeted therapies

ROS1 is a pivotal transmembrane receptor protein tyrosine kinase which regulates several cellular processes like apoptosis, survival, differentiation, proliferation, cell migration, and transformation.

Current Medicinal Chemistry 2016 vol. 23 # 2 p. 142 – 160

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