171745-13-4 Usage
Uses
Used in Pharmaceutical Industry:
4-[(3-BROMOPHENYL)AMINO]-6,7-DIETHOXYQUINAZOLINE is used as a potent and specific inhibitor of the tyrosine kinase activity of the epidermal growth factor. This application is significant because the inhibition of tyrosine kinase activity can help regulate cell growth and proliferation, making it a potential therapeutic target for various cancers and other diseases characterized by uncontrolled cell growth.
Additionally, due to its unique chemical structure, 4-[(3-BROMOPHENYL)AMINO]-6,7-DIETHOXYQUINAZOLINE may have potential applications in other industries, such as materials science or chemical research, depending on its specific properties and reactivity. Further investigation and research would be required to explore these possibilities.
Biological Activity
compound 56, 4-[(3-bromophenyl)amino]-6,7-diethoxyquinazoline, is a potent and specific inhibitor of the tyrosine kinase of the epidermal growth factor receptor (egfr) showing an ic50 of 0.006 nm. it competitively binds at the adenosine-triphosphate (atp) site of egfr. compound 56 is capable of inhibiting the phosphorylation of egf-dependent egfr, suppressing the proliferation and clonogenicity of a wide panel of egfr-overexpressing human cancer lines, and blocking egf-mediated mitogenesis and oncogenic transformation in fibroblasts overexpressing egfr. besides inhibiting egfr tyrosine kinase, it also inhibits the tyrosine kinase of human epidermal growth factor receptor 2 (her2/neu) but with a less potency.bridges aj, zhou h, cody dr, rewcastle gw, mcmichael a, showalter hd, fry dw, kraker aj, and denny wa. tyrosine kinase inhibitors. 8. an unusually steep structure-activity relationship for analogues of 4-(3-bromoanilino)-6,7-dimethoxyquinazoline (pd 153035), a potent inhibitor of the epidermal growth factor receptor.j med chem 1966; 39 (1): 267-276monique bos, jhn mendelsohn, young-mee kim, joan albanell, david w. fry, and jose baelga. pd153035, a tyrosine kinase inhibitor, prevents epidermal growth factor receptor activation and inhibits growth of cancer cells in a receptor number-dependent manner. clin cancer res 1997;3:2099-2106
Check Digit Verification of cas no
The CAS Registry Mumber 171745-13-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,7,1,7,4 and 5 respectively; the second part has 2 digits, 1 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 171745-13:
(8*1)+(7*7)+(6*1)+(5*7)+(4*4)+(3*5)+(2*1)+(1*3)=134
134 % 10 = 4
So 171745-13-4 is a valid CAS Registry Number.
171745-13-4Relevant articles and documents
Allosteric inhibition of fructose-1,6-bisphosphatase by anilinoquinazolines
Wright, Stephen W.,Hageman, David L.,McClure, Lester D.,Carlo, Anthony A.,Treadway, Judith L.,Mathiowetz, Alan M.,Withka, Jane M.,Bauer, Paul H.
, p. 17 - 21 (2007/10/03)
Anilinoquinazolines currently of interest as inhibitors of tyrosine kinases have been found to be allosteric inhibitors of the enzyme fructose 1,6-bisphosphatase. These represent a new approach to inhibition of F16BPase and serve as leads for further drug design. Enzyme inhibition is achieved by binding at an unidentified allosteric site. (C) 2000 Elsevier Science Ltd.
Tyrosine kinase inhibitors. 8. An unusually steep structure-activity relationship for analogues of 4-(3-bromoanilino)-6,7-dimethoxyquinazoline (PD 153035), a potent inhibitor of the epidermal growth factor receptor
Bridges,Zhou,Cody,Rewcastle,McMichael,Showalter,Fry,Kraker,Denny
, p. 267 - 276 (2007/10/03)
4-(3-Bromoanilino)-6,7-dimethoxyquinazoline (32, PD 153035) is a very potent inhibitor (IC50 0.025 nM) of the tyrosine kinase activity of the epidermal growth factor receptor (EGFR), binding competitively at the ATP site. Structure-activity relationships for close analogues of 32 are very steep. Some derivatives have IC50s up to 80-fold better than predicted from simple additive binding energy arguments, yet analogues possessing combinations of similar phenyl and quinazoline substituents do not show this 'supra-additive' effect. Because some substituents which are mildly deactivating by themselves can be strongly activating when used in the correct combinations, it is proposed that certain substituted analogues possess the ability to induce a change in the conformation of the receptor when they bind. There is some bulk tolerance for substitution in the 6- and 7-positions of the quinazoline, so that 32 is not the optimal inhibitor for the induced conformation. The diethoxy derivative 56 [4-(3-bromoanilino)- 6,7-diethoxy-quinazoline] shows an IC50 of 0.006 nM, making it the most potent inhibitor of the tyrosine kinase activity of the EGFR yet reported.
