Leboho Tlabo C, Michael Joseph P, van Otterlo Willem A L, van Vuuren Sandy F, de Koning Charles B
Molecular Sciences Institute, School of Chemistry, University of the Witwatersrand, South Africa.
Bioorg Med Chem Lett. 2009 Sep 1;19(17):4948-51. doi: 10.1016/j.bmcl.2009.07.091. Epub 2009 Jul 22.
A series of 2- and 3-aryl substituted indoles and two 1,3,4,5-tetrahydropyrano[4,3-b]indoles were synthesized from indole and 5-methoxyindole. The 2-aryl indoles were synthesized from the 1-(phenylsulfonyl)indole derivatives using magnesiation followed by iodination. The 2-iodinated compounds were then subjected to Suzuki-Miyaura reactions. In addition, the 3-aryl indoles were made from the corresponding 3-bromoindoles using Suzuki-Miyaura reactions. The 1,3,4,5-tetrahydropyrano[4,3-b]indoles were also synthesized from 1-(phenylsulfonyl)indole by magnesiation followed by treatment with allylbromide. The product was then converted into [2-allyl-1-(phenylsulfonyl)-1H-indol-3-yl]methanol which upon exposure to Hg(OAc)(2) and NaBH(4) afforded tetrahydropyrano[4,3-b]indoles. A number of the 2- and 3-aryl indoles displayed noteworthy antimicrobial activity, with compound 13a displaying the most significant activity (3.9 microg/mL) against the Gram-positive micro-organism Bacillus cereus.
以吲哚和5-甲氧基吲哚为原料，合成了一系列2-芳基和3-芳基取代的吲哚以及两种1,3,4,5-四氢吡喃并[4,3 -b]吲哚。2-芳基吲哚由1-(苯磺酰基)吲哚衍生物经镁化反应后碘化反应合成。然后将2-碘化化合物进行铃木-宫浦反应。此外，3-芳基吲哚由相应的3-溴吲哚通过铃木-宫浦反应制得。1,3,4,5-四氢吡喃并[4,3 -b]吲哚也由1-(苯磺酰基)吲哚经镁化反应后用烯丙基溴处理合成。产物随后转化为[2-烯丙基-1-(苯磺酰基)-1H-吲哚-3-基]甲醇，该化合物在Hg(OAc)₂和NaBH₄作用下得到四氢吡喃并[4,3 -b]吲哚。许多2-芳基和3-芳基吲哚表现出显著的抗菌活性，化合物13a对革兰氏阳性微生物蜡状芽孢杆菌显示出最显著的活性(3.9μg/mL)。
