A boron-containing estrogen mimic.
A boron-containing estrogen mimic.
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一种含硼雌激素模拟物。
DOI：
10.1107/s0108270199007520
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发表时间：
1999
期刊：
影响因子：
--
通讯作者：
Groziak,MP
中科院分区：
文献类型：
--
作者：
Robinson,PD;Groziak,MP
描述了一类新的基于2，3，1-苯并二氮杂硼的雌激素模拟物的原型。得到1，2-二氢-1，6-二羟基-2-（2-甲氧基-6-吡啶基）-2，3，1-苯并二氮杂硼杂环戊烯（6），其为结晶一水合物（Cl 3 HI 2 BN 3 O 3）。H2O）后，区域选择性BBr-介导的0-脱甲基化的缩合产物形成的2-甲酰基-4-甲氧基苯硼酸和2-肼基-6-甲氧基吡啶。如设计所预期的，（6）的固态结构的特征在于供体B-OH基团和受体吡啶环N之间的分子内氢键缔合，该连接构成另外的“虚拟”六元环，从而提供与四环甾族化合物紧密匹配的总体拓扑图。具体而言，原型（6）可被视为二氢马钱宁或雌二醇的O 17-甲基醚衍生物的含硼模拟物。
A prototype of a new class of 2, 3, 1-benzodiaza-borine-based estrogen mimics is described. 1, 2-Dihydro-1, 6-dihydroxy-2-(2-methoxy-6-pyridyl)-2, 3, 1-benzodi-azaborine,(6), was obtained as a crystalline mono-hydrate (CI3HI2BN303. H20) after regioselective BBr~-mediated O-demethylation of the condensation product formed from 2-formyl-4-methoxybenzeneboronic acid and 2-hydrazino-6-methoxypyridine. As intended by design, the solid-state structure of (6) features an intramolecular hydrogen-bond association between the donor B--OH group and the acceptor pyridine ring N, a connection which constitutes an additional'virtual'six-membered ring, thereby providing for an overall top-ography closely matching that of a tetracyclic steroid. Specifically, prototype (6) can be viewed as a boron-containing mimic of the O17-methyl ether derivatives of dihydroequilenin or estradiol.