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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 43, Number 3
JKCSEZ 43(3)
June 20, 1999 

Studies on the Synthesis of Geminal Bisphosphono Amine Derivatives Using Pentacovalent Oxaphospholenes

5배위 결합된 옥사포스포린을 이용한 제미널 비스포스포노 아민 유도체의 합성에 관한 연구
Mi-Young Lee, Kang-Yeoun Jung

이미영, 정강연
제미널 비스포스폰에이트기를 포함하는 화합물들은 칼슘과 관련된 다양한 질병들 즉 Paget's disease, 악성칼슘과다증, 골다공증등에 약효가 있는 것으로 잘 알려져 있다. 이러한 화합물을 합성하기 위하여 먼저 methylvhyl ketone과 triethylphosphite를 가지고 5배위된 옥사포스포린 화합물을 합성하였다. 이렇게 합성된 5배위 결합된 옥사포스프린을 bromination, 응용된 Westheimer반응, 그리고 가수분해를 통해서 ㅏketo-bisphosphonates를 얻을 수 있었다. 그리고 이 ㅏketobisphosphonates 화합물들은 환원성아민화를 이용해서 N-알킬화된 ㅏaminobisphosphonates로 전환하였다. 이렇게 합성된 2차아민 형태의 N-알킬화된 ㅏaminobisphosphonates는 N-알킬화반응으로 3차아민을 만든 후 N,N디알킬화된 -aminobisphosphonates 화합물로 합성할 수 있었다.

Geminal bisphosphonates have been well known to be effective inhibitors of various calciumrelated disorders such as Paget's disease, hypercalcemia of malignancy, and osteoporosis. To synthesize bisphosphonates, we have used the pentacovalent oxaphospholene prepared from methyl vinyl ketone and triethyl-phosphite. Υ-Ketobisphosphonates are obtained by bromination, applied Westheimer reaction, and hydrolysis of synthesized oxaphospholene. This compound was converted to the N-alkylated Υ-aminobisphosphonates by the reductive amination. Conversion of the resulting secondary amine to the tertiary one, followed by introduction of the second alkyl group on the nitrogen, was led to the synthesis of new N,N'-dialkylated Υ-aminobisphosphonates.

294 - 301
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