Scatena Gabriel S, Cassiano Neila M, Netto Chaquip D, Costa Paulo R R, Cass Quezia B, Batista João M
Department of Chemistry, Federal University of São Carlos - UFSCar, São Carlos, Brazil.
Federal University of Rio de Janeiro - UFRJ, Macaé, Brazil.
Chirality. 2017 May;29(5):167-171. doi: 10.1002/chir.22696. Epub 2017 Apr 12.
The racemic pterocarpanquinone LQB-118 is active, in mice and hamsters, against tegumentary and visceral leishmaniasis. This compound also presents antiinflammatory and antineoplastic activity in mice. The low level of toxicity observed in these studies makes LQB-118 a promising drug candidate. In order to conduct further biological testing to investigate enantioselectivity in the above-mentioned activities, a multimilligram amount of each enantiomer of LQB-118 was produced. Furthermore, vibrational circular dichroism (VCD) and Density Functional Theory (DFT) calculations were used to determine unambiguously their absolute configurations. The comparison of experimental and calculated VCD data led to the assignment of (-)-LQB-118 as 7aR,12aR and, consequently, (+)-LQB-118 as 7aS12aS.
外消旋紫檀芪醌LQB - 118在小鼠和仓鼠体内对皮肤型和内脏型利什曼病具有活性。该化合物在小鼠体内还具有抗炎和抗肿瘤活性。这些研究中观察到的低毒性水平使LQB - 118成为一种有前景的候选药物。为了进行进一步的生物学测试以研究上述活性中的对映选择性，制备了多毫克量的LQB - 118的每种对映体。此外，使用振动圆二色性（VCD）和密度泛函理论（DFT）计算来明确确定它们的绝对构型。实验和计算的VCD数据的比较导致将（-）-LQB - 118指定为7aR，12aR，因此，（+）-LQB - 118为7aS，12aS。
