Basic information
- CAS
194423-06-8- Standard SMILES
CC#CC(=O)Nc1ccc2ncnc(Nc3cccc(Br)c3)c2c1- InChIKey
BTYYWOYVBXILOJ-UHFFFAOYSA-N- Molecular formula
- C18H13BrN4O
- Average molar mass
- 381.2 g/mol
- Monoisotopic mass
- 380.02727314
Overview
N-{4-[(3-bromophenyl)amino]quinazolin-6-yl}but-2-ynamide is a member of the class of quinazolines that is 4,6-diaminoquinazoine in which the one of the hydrogens attached to the amino group at position 4 has been replaced by a m-bromophenyl group while one of the hydrogens attached to the amino group at position 6 has been replaced by a but-2-ynoyl group. It has a role as an antineoplastic agent, an EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor and an epidermal growth factor receptor antagonist. It is a secondary carboxamide, a member of bromobenzenes, a member of quinazolines and a ynamide.
Names & identifiers
- Preferred name
- N-(4-((3-bromophenyl)amino)-6-quinazolinyl)-2-butynamide
- IUPAC
- N-[4-(3-bromoanilino)quinazolin-6-yl]but-2-ynamide
- English name
- 2-ButynaMide, N-[4-[(3-broMophenyl)aMino]-6-quinazolinyl]-
- Molecular formula
- C18H13BrN4O
- Molecular weight
- 381.23
Names & synonyms
194423-06-8cl-387785N-[4-[(3-Bromophenyl)amino]-6-quinazolinyl]-2-butynamideEKB-785WAY-EKI-785B4W27J1Z8BDTXSID4012365392-Butynamide, N-(4-((3-bromophenyl)amino)-6-quinazolinyl)-2-Butynamide, N-[4-[(3-bromophenyl)amino]-6-quinazolinyl]-N-(4-((3-bromophenyl)amino)-6-quinazolinyl)-2-butynamideN-[4-[(3-bromophenyl)amino]-6-quinazolinyl)-2-butynamideN-{4-[(3-bromophenyl)amino]-6-quinazolinyl}-2-butynamide
Show more names
785CL-387CS-1630EKB 785-387785CL-38875WAY-EKI 785CL-387785, >=98%EKI-785 CL-38875
RefChem:926802DTXCID301631306EKI-785N-(4-((3-bromophenyl)amino)quinazolin-6-yl)but-2-ynamideN-[4-(3-bromoanilino)quinazolin-6-yl]but-2-ynamideMFCD02179194CL-387,785CL-387785 (EKI-785)
Database identifiers
Properties
Computed structural properties
- XLogP
- 4.3
- Topological polar surface area
- 66.9 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 3
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 514
Physicochemical properties
- Melting point
- 276 °C · 276 °C
- Density
- 1.577 · 1.577±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Sealed in dry,Store in freezer, under -20°C
- solubility
- 2 O; · insoluble in EtOH; insoluble in H2O; ≥16.85 mg/mL in DMSO
- pka
- 9.84 · 9.84±0.43(Predicted)
- form
- Off-white to yellow solid.
- color
- White to Orange to Green
- InChI
- 1S/C18H13BrN4O/c1-2-4-17(24)22-14-7-8-16-15(10-14)18(21-11-20-16)23-13-6-3-5-12(19)9-13/h3,5-11H,1H3,(H,22,24)(H,20,21,23)
- InChIKey
- BTYYWOYVBXILOJ-UHFFFAOYSA-N
- SMILES
- Brc1cc(ccc1)Nc2ncnc3c2cc(cc3)NC(=O)C#CC
- FDA UNII
- 4 W27J1Z8B · B4W27J1Z8B
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 77 · NA.77
- WGK Germany
- 1 · WGK 1
- HS Code
- 2933.59 · 2933.59.5300
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- WGK 1
- hs_code
- 2933.59.5300
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationAgents that inhibit PROTEIN KINASES.
Applications
DescriptionOveractivity of epidermal growth factor receptor (EGFR) tyrosine kinase activity has been associated with a number of cancers. CL 387,785 is a potent, irreversible inhibitor of EGFR kinase activity (IC50 = 370 pM). It blocks EGF-stimulated autophosphorylation of receptors in cells (IC50 = 5 nM) and halts cell cycling in cells that overexpress EGFR or c-ErbB2 (IC50s = 31-125 nM). CL 387,785 profoundly blocks the growth of EGFR-overexpressing tumors in nude mice when given orally at 80 mg/kg/day for 10 days.
UsesCL-387785 (EKI-785) is an irreversible and selective EGFR inhibitor showing activity against mutations of the receptor. Potential therapeutic against various type of cancer, including lung cancer.
Upstream & downstream products
Upstream raw materials
Suppliers76 total
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
Related reactions
10 records
Compound notes
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