Boron Analogues of Pyrophosphates

Pyrophosphates with (P—O—P) linkage and methylene bisphosphonates (P—CH2—P) have been shown to possess potent anti-viral activity against

OH

ClH3N

Figure 2.22 Boronated amines

ii h2 ii

II H2 II

Pyrophosphate Methylene bisphosphonates Boron analogues

Figure 2.23 Analogues of pyrophosphates the growth of Herpes viruses as well as other viruses. Phosphonoacetic acid and phosphonoformic acid derivatives have been clinically proven to be effective against a host of viral diseases.51 Pyrophosphates also play a significant role in the regulation of the calcification and decalcification process in vivo and are, therefore, important in calcium metabolism and prevention of bone disorders.51 Unfortunately, due to low hydrolytic stability, in vivo therapeutic use of pyrophosphates is limited. Bisphosphonates, on the other hand, have widespread use for treating bone disorders, such as Paget's disease.51 A dihydroboride group (BHD is isoelectronic with atomic oxygen and the methylene group. Thus, the boron analogues of pyrophosphates and geminal bisphosphonates in which the bridging oxygen or methylene group is replaced with a dihydroboron group have been synthesized (Figure 2.23). A significant difference between the boron and non-boron analogues is the additional negative charge accompanying boron substitution.

The synthetic scheme to prepare boron analogues of pyrophosphates is given in Scheme 2.2. These boron analogues, which have an additional positive charge, are being evaluated for their anti-viral activities.

Ph3C+BF4

Scheme 2.2 Synthesis of boronated pyrophosphates

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