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The Williamson ether synthesis is an organic reaction, forming an ether from an organohalide and a deprotonated alcohol (alkoxide). This reaction was developed by Alexander Williamson in 1850. Typically it involves the reaction of an alkoxide ion with a primary alkyl halide via an SN2 reaction. This reaction is important in the history of organic chemistry because it helped prove the structure of ethers.
Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion or a carbene (or their equivalents). An alkyl group is a piece of a molecule with the general formula CnH2n+1, where n is the integer depicting the number of carbons linked together. For example, a methyl group (n = 1, CH3) is a fragment of a methane molecule (CH4). Alkylating agents use selective alkylation by adding the desired aliphatic carbon chain to the previously chosen starting molecule. This is one of many known chemical syntheses. Alkyl groups can also be removed in a process known as dealkylation. Alkylating agents are often classified according to their nucleophilic or electrophilic character.
Aziridine is an organic compound consisting of the three-membered heterocycle (CH2)2NH. It is a colorless, toxic, volatile liquid that is of significant practical interest. Its derivatives, also referred to as aziridines, are of broader interest in medicinal chemistry.
Bromoethane, also known as ethyl bromide, is a chemical compound of the haloalkanes group. It is abbreviated by chemists as EtBr. This volatile compound has an ether-like odor.
Ethyl bromoacetate is the chemical compound with the formula CH2BrCO2C2H5. It is the ethyl ester of bromoacetic acid and is prepared in two steps from acetic acid. It is a lachrymator and has a fruity, pungent odor. It is also a highly toxic alkylating agent and may be fatal if inhaled.
Dacarbazine (DTIC), also known as imidazole carboxamide, is a chemotherapy medication used in the treatment of melanoma and Hodgkin's lymphoma. For Hodgkin's it is often used together with vinblastine, bleomycin, and doxorubicin. It is given by injection into a vein.
Altretamine is an antineoplastic agent. It was approved by the U.S. FDA in 1990.
Nitrosourea is both the name of a molecule, and a class of compounds that include a nitroso (R-NO) group and a urea.
Lomustine (INN); abbreviated as CCNU; original brand name CeeNU, now marketed as Gleostine) is an alkylating nitrosourea compound used in chemotherapy. It is closely related to semustine and is in the same family as streptozotocin. It is a highly lipid-soluble drug, thus it crosses the blood-brain barrier. This property makes it ideal for treating brain tumors, which is its primary use, although it is also used to treat Hodgkin lymphoma as a second-line option. Lomustine has a long time to nadir.
Carmustine, sold under the brand name BiCNU among others, is a medication used mainly for chemotherapy. It is a nitrogen mustard β-chloro-nitrosourea compound used as an alkylating agent.
Ada, also called as O6 alkyl guanine transferase I (O6 AGT I), is an enzyme induced by treatment of bacterial cells with alkylating agents that mainly cause methylation damage. This phenomenon is called the adaptive response hence the name. Ada transfers the alkyl group from DNA bases and sugar-phosphate backbone to a cysteine residue, inactivating itself. Consequently, it reacts stoichiometrically with its substrate rather than catalytically and is referred to as a suicide enzyme. Methylation of Ada protein converts it into a self transcriptional activator, inducing its own gene expression and the expression of other genes which together with Ada help the cells repair alkylation damage. Ada removes the alkyl group attached to DNA bases like guanine (O6-alkyl guanine) or thymine (O4-alkyl thymine) and to the oxygen of the phosphodiester backbone of the DNA. However, Ada shows greater preference for O6- alkyl guanine compared to either O4-thymine and alkylated phosphotriesters. Ada enzyme has two active sites, one for the alkylated guanines and thymines and the other for alkylated phosphotriesters.
An alkylating antineoplastic agent is an alkylating agent used in cancer treatment that attaches an alkyl group (CnH2n+1) to DNA.
ICE in the context of chemotherapy is an acronym for one of the chemotherapy regimens, used in salvage treatment of relapsed or refractory non-Hodgkin's lymphoma and Hodgkin lymphoma.
Chlornaltrexamine is an irreversible mixed agonist–antagonist for μ-opioid receptors, which forms a covalent bond to the active site. It is 22 times more potent than morphine. Its alkylating group is a bis(chloroalkyl)amino-residue similar to that of the nitrogen mustards.
Benzilylcholine mustard is a modified version of acetylcholine, so named because after cyclization in solution it forms an iminium derivative that is structurally similar to benzilylcholine. It is well known for being an irreversible antagonist of the muscarinic acetylcholine receptor. It has been used in pharmacological experiments investigating the relationship between receptor occupancy and response. It was also one of the tools in characterization of the muscarinic acetylcholine receptor.
In DNA repair, the Ada regulon is a set of genes whose expression is essential to adaptive response, which is triggered in prokaryotic cells by exposure to sub-lethal doses of alkylating agents. This allows the cells to tolerate the effects of such agents, which are otherwise toxic and mutagenic.
CEPP is an acronym for the name of a chemotherapy regimen that is intended for treatment of aggressive non-Hodgkin lymphomas. Unlike CHOP, this chemotherapy regimen does not contain doxorubicin or any other anthracycline. Thus, it can be used in patients with severe cardiovascular diseases and contraindications for doxorubicin-containing regimens. There are 2 modifications of CEPP - with the addition of bleomycin, called CEPP (B), and without bleomycin - ordinary CEPP.
Irazepine is a benzodiazepine derivative containing isothiocyanate functional group. It is a non-competitive benzodiazepine binding site antagonist. Irazepine and other alkylating benzodiazepine, kenazepine, bind to brain benzodiazepine receptors in a non-competitive (covalent) fashion in vitro, and may exert a long-lasting anticonvulsant effect.
Melphalan flufenamide, sold under the brand name Pepaxto, is an anticancer medication used to treat multiple myeloma.
Methyl 2-bromoacetate (methyl bromoactate) is a chemical compound with the molecular formula C3H5BrO2.
References
- ↑ Römpp CD 2006, Georg Thieme Verlag 2006
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