19916-73-5 Usage
Description
6-O-Benzylguanine, also known as O6-Benzylguanine, is an organic compound that serves as an irreversible inhibitor of the mammalian DNA repair protein, O6-alkylguanine-DNA alkyltransferase. It is a light yellow solid and plays a crucial role in the protection against carcinogenic and therapeutic alkylating agents.
Uses
1. Used in Anticancer Applications:
6-O-Benzylguanine is used as an anticancer agent for its effectiveness as a substrate and efficient inactivator of DNA alkyltransferase. It acts as an inhibitor of MGMT, a protein involved in DNA repair, which can help enhance the efficacy of certain chemotherapy treatments.
2. Used in Organic Synthesis:
6-O-Benzylguanine is used as an important raw material and intermediate in organic synthesis, contributing to the development of various chemical compounds.
3. Used in Pharmaceutical Industry:
In the pharmaceutical industry, 6-O-Benzylguanine is utilized as a key component in the synthesis of drugs targeting DNA repair mechanisms, potentially leading to the development of novel therapeutics for cancer treatment.
4. Used in Agrochemicals:
6-O-Benzylguanine is also used as a raw material and intermediate in the agrochemical industry, where it may contribute to the development of new compounds for pest control and crop protection.
5. Used in Dyestuff Industry:
In the dyestuff industry, 6-O-Benzylguanine serves as a valuable intermediate for the synthesis of various dyes and pigments, enhancing the color properties and performance of these products.
Biochem/physiol Actions
O6-Benzylguanine (O6BG) inhibits methylguanine methyltransferase (MGMT) by blocking the active site through benzyl group transfer. The use of O6BG with bis-chloroethylnitrosourea (BCNU) or carmustine is effective in treating solid tumors including lymphomas, melanomas and sarcoma.
Check Digit Verification of cas no
The CAS Registry Mumber 19916-73-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,9,9,1 and 6 respectively; the second part has 2 digits, 7 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 19916-73:
(7*1)+(6*9)+(5*9)+(4*1)+(3*6)+(2*7)+(1*3)=145
145 % 10 = 5
So 19916-73-5 is a valid CAS Registry Number.
InChI:InChI=1/C12H11N5O/c13-12-16-10-9(14-7-15-10)11(17-12)18-6-8-4-2-1-3-5-8/h1-5,7H,6H2,(H3,13,14,15,16,17)
19916-73-5Relevant articles and documents
Regioselective alkylation of guanine derivatives in the synthesis of peptide nucleic acid monomers
Dezhenkov,Cheshkov,Prokhorov,Dezhenkova,Shvets,Kirillova, Yu. G.
, p. 1100 - 1106 (2015)
A method for the synthesis of 6-O-benzyl- and 6-O-benzyl-2-N-benzyloxycarbonyl-protected guanine derivatives starting from 2-amino-6-chloropurin is described. A regioselective alkylation of these N(9)-protected guanine derivatives gave the corresponding α-monomers of chiral peptide nucleic acids, the L-glutamic acid derivatives. It was shown that these compound do not inhibit (in the concentrations -1) the topoisomerase I activity.
Synthesis and biological evaluation of new HIV-1 protease inhibitors with purine bases as P2-ligands
Zhu, Mei,Dong, Biao,Zhang, Guo-Ning,Wang, Ju-Xian,Cen, Shan,Wang, Yu-Cheng
supporting information, p. 1541 - 1545 (2019/04/25)
Introducing purine bases to P2-ligands might enhance the potency of Human Immunodeficiency Virus-1 (HIV-1) protease inhibitory because of the carbonyl and NH groups promoting the formation of extensive H-bonding interactions. In this work, thirty-three compounds are synthesized and evaluated, among which inhibitors 16a, 16f and 16j containing N-2-(6-substituted-9H-purin-9-yl)acetamide as the P2-ligands along with 4-methoxylphenylsulfonamide as the P2′-ligand, display potent inhibitory effect on the activity of HIV-1 protease with IC50 43 nM, 42 nM and 68 nM in vitro, respectively.
Benzyl guanine derivative, an organic salt compound thereof, a medicine composition, and application thereof
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Paragraph 0052; 0056; 0057; 0061; 0062; 0063; 0064, (2017/09/26)
The invention relates to the field of antitumor medicines and especially relates to a benzyl guanine derivative, an organic salt compound thereof, a medicine composition, and an application thereof. The benzyl guanine derivative is easy to prepare, has good druggability, can inhibit enzyme-catalysis activity of Pin 1 protein, can improve biosynthesis of mature microRNA at cellular and animal levels, and increases the types of antitumor medicines.