Mustard compounds

The nitrogen mustards, compounds that incorporate a few-chloroethylamino moiety, have a venerable history as cytotoxic agents used in cancer chemotherapy. 

Other Names Alkeran , L-Sarcolysine, L-PAM, L-Phenylalanine Mustard, Compound CB 3025, Compound NSC-8806. 

Others were honored guests. Charlotte Auerbach suffered serious burns and rashes from the mustard compounds she used in her mutagenesis experiments in the 1940s (Beale 1993). 

Brock N. 1976. Comparative pharmacologic study in vitm and in vivo with cyclophosphamide (NSC-26271), cyclophosphamide metabolites, and plain nitrogen mustard compounds. Cancer Treat Rep 60 301-307. 

The nitrogen mustard compound mechlorethamine (Fig 6.10) was the first alkylating agent to be used (1942). The nitrogen atom is able to displace a chloride ion intra-molecularly to form the highly electrophilic aziridine ion. Alkylation of DNA can then take place. Since the process can be repeated, cross-linking between chains will occur. 

Mitomycin C is a natural product sometimes classified as an antitumor antibiotic (see Table 124—15). It has functional similarities to nitrogen mustard compounds and may function as an alkylating agent, although its toxicity pattern differs from conventional alkylators. 

It can be shown that aromatic nitrogen mustards (compounds containing an aromatic ring) usually alkylate via the SN, mechanism. 

Bradykinin 82-84 Carrageenan Formalin Brewer s yeast Silver nitrate Turpentine Trypsin Kaolin Mustard Compound 48/80 Potassium cyanide Monoiodoacetic acid Sodium fluoride Hyaluronidase 81, 90-92 77, 79, 80, 81, 85, 86, 93-96 55,81,91,97-101 102 86 55 103 81, 104 18, 76, 77 85 85 85 21, 77, 87... 

The IT-SIMS was also applied for the characterization of soil samples contaminated with nitrogen mustard compounds [16]. These are much less common than sulfur mustards and are comprised by three compounds tris(2-chloroethyl)amine (HN-3), bis(2-chloroethyl)methyl-amine (HN-2), and bis(2-chloroethyl)ethylamine (HN-1). Of these, only HN-3 received serious consideration... 

The uridine mustard compound (49) has been synthesized for antitumour evaluation. 09 Oligodeoxynucleosides of type (50), and related trimers, have been prepared by coupling 3 -(7-carboxymethyI derivatives with 5 -aminodeoxy-compounds."0... 

An imposing number of organoarsenic and mustard compounds have been tried out for use as chemical agents. Many of them were rejected because they lacked toxicity or on account of tactical drawbacks. In the case of mustard -type blister agents, the number was increased until 1945 by manifold tactical formulations. The arsenicals of German war production are listed in Table 1 [1] [2]. The basic "mustard gas" compounds may be found in Table 2 [1] [2] and tactical mixtures are summarized in Table 3 [2]. 

---