Alkylating agents, list

Drags used to treat cancer are subdivided into six groups antimetabolites, alkylating agents, antibiotics, drags isolated from plants, hormones, and a group of substances not included in the classifications listed above, which are examined in another section. 

Exercise 17-29 If you wished to prepare the methyl ether of 4-hydroxy-3-penten-2-one by O-alkylation, what base and which of the methylating agents listed would you... 

Chloromethyl methyl ether and bis-chloromethyl ether (CICH2 OCH2Cl) in common with several alkylating agents possess carcinogenic properties in experimental animals and have been listed as assumed human carcinogens similar hazardous properties associated with dichloromethyl methyl ether have not been reported but it would be prudent to handle this compound with due care. 

Fig. 2.23. Alkylating agents with structural elements that can act as neighboring groups in SN reactions. (In the example listed in parentheses, the neighboring group participation initiates an alkylation of the aromatic compound, in which an external nucleophile is not participating at all.)...

Table 2 lists examples of monoalkylation reactions of ketone a,p-dianions. The dianions always react with alkylating agents at the /3-carbon atom to generate the corresponding lithium enolates, which can be quenched by water or electrophiles such as TMSC1 and PhSSPh. The last two examples demonstrate the results of the single alkylation reaction of a ketone a,5-dianion with hexyl and allyl bromides, which occurs at the 5-position to give lithium Z-enolates. 

Table 3.6 lists the long-term mustard complications affecting the respiratory tract, the eyes, the skin, the central nervous system and the bone marrow (8,25,26). As alkylating agents, sulfur and nitrogen mustards are carcinogens. 

The bifunctional alkylating agents also inhibit RNA and protein synthesis, especially at higher doses. Interference with other cellular reactions should not be ruled out. Table 4-3 lists some of the important alkylating agents currently in use. 

A mixture of fluorosulfonic acid and dimethyl sulfate distilled in glass -> methyl fluorosulfonate. Y > 80%. - Fluorosulfonic acid esters are excellent alkylating agents. F. e. and listing of good alkylating agents s. M. G. Ahmed et al., Chem. Commun. 1968, 1533. 

In order to facilitate the use of the tables in this chapter, they have been organized as follows The substrates are listed in order of increasing (total) number of carbons. The list of substances used as alkylating agents is likewise in order of increasing carbon number and in order of increasing complexity within a set of isomers or closely related compounds. 

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