23079-73-4Relevant academic research and scientific papers
Anibamine and Its Analogues: Potent Antiplasmodial Agents from Aniba citrifolia
Du, Yongle,Valenciano, Ana Lisa,Dai, Yumin,Zheng, Yi,Zhang, Feng,Zhang, Yan,Clement, Jason,Goetz, Michael,Kingston, David G. I.,Cassera, Maria B.
supporting information, p. 569 - 577 (2019/10/16)
In our continuing search for novel natural products with antiplasmodial activity, an extract of Aniba citrifolia was found to have good activity, with an IC50 value less than 1.25 μg/mL. After bioassay-directed fractionation, the known indolizinium alkaloid anibamine (1) and the new indolizinium alkaloid anibamine B (2) were isolated as the major bioactive constituents, with antiplasmodial IC50 values of 0.170 and 0.244 μM against the drug-resistant Dd2 strain of Plasmodium falciparum. The new coumarin anibomarin A (3), the new norneolignan anibignan A (5), and six known neolignans (7-12) were also obtained. The structures of all the isolated compounds were determined based on analyses of 1D and 2D NMR spectroscopic and mass spectrometric data, and the absolute configuration of anibignan A (5) was assigned from its ECD spectrum. Evaluation of a library of 28 anibamine analogues (13-40) indicated that quaternary charged analogues had IC50 values as low as 58 nM, while uncharged analogues were inactive or significantly less active. Assessment of the potential effects of anibamine and its analogues on the intraerythrocytic stages and morphological development of P. falciparum revealed substantial activity against ring stages for compounds with two C-10 side chains, while those with only one C-10 side chain exhibited substantial activity against trophozoite stages, suggesting different mechanisms of action.
Structure activity relationship studies of natural product chemokine receptor CCR5 antagonist anibamine toward the development of novel anti prostate cancer agents
Zhang, Feng,Arnatt, Christopher K.,Haney, Kendra M.,Fang, Harrison C.,Bajacan, John E.,Zhang, Yan,Richardson, Amanda C.,Ware, Joy L.
, p. 395 - 408,14 (2020/07/30)
Recent studies have indicated that the CCR5 chemokine receptor may be a potential target for treating prostate cancer. Thus, development of CCR5 antagonists may provide novel prostate cancer therapy. Anibamine, a novel pyridine quaternary alkaloid isolated from Aniba sp., was found to effectively compete with 125I-gp120 in binding to the chemokine receptor CCR5, with an IC50 = 1 μM. Anibamine is the first natural product reported as a CCR5 antagonist, and thus provides a novel structural skeleton unique from other lead compounds that have generally been identified from high-throughput screening efforts. In order to refine the lead compound's structure and improve the therapeutic index of anibamine derivatives as potential anti prostate cancer agents, the approach of "deconstruction- reconstruction-elaboration" was applied in the structure-activity relationship studies of this work. Here, we report the design, syntheses and anti prostate cancer activities of anibamine and 17 analogues. The results from the in vitro and in vivo studies described here show that this class of compounds has potential to provide novel leads as anti prostate cancer agents.
Conformational control and photoenolization of pyridine-3-carboxaldehydes in the solid state: Stabilization of photoenols via hydrogen bonding and electronic control
Mal, Prasenjit,Lourderaj,Parveen,Venugopalan,Moorthy, J. Narasimha,Sathyamurthy
, p. 3446 - 3453 (2007/10/03)
We have investigated the solid-state photobehavior of a broad set of pyridine-3-carboxaldehydes 1-5. The introduction of a heteroatom into mesitaldehydes as in aldehydes 1 raises the question of conformational preference in the solid state. The preferred conformations have been unequivocally established from X-ray crystal structure analyses of two of the aldehydes, 1c and 2c; it is shown that intramolecular hydrogen bonding could be utilized to achieve conformational control. In contrast to mesitaldehydes, which undergo efficient photocyclization to benzocyclobutenols in the solid state, the heteroatom analogues 1b and 1c exhibit a perceptible color change (from colorless to pale yellow for 1b and yellow-orange for 1c) upon UV irradiation; the color attributed to (E)-enols is persistent for several hours. Continued irradiation leads to an intractable polymeric material. The AM1 calculations, which have been reliably applied to the thermal cyclization of xylylenols to benzocyclobutenols, reveal that the (E)-enols of 1 are more stable than those of the mesitaldehydes relative to their corresponding benzocyclobutenols. The stabilization is interpreted as arising from the possibility of engaging the heteroatom in resonance delocalization. That the contribution from such a role of the nitrogen atom is so pronounced is elegantly demonstrated by forming the fluoroborate salts; 1a-HBF4 and 1b-HBF4 readily exhibit highly red-shifted absorption upon exposure to UV radiation as a result of stabilization of the photoenols. Notably, such a remarkable stabilization via electronic control of the photoenols is unprecedented. All of the 2-methoxy- and 2-chloro-substituted aldehydes 2-5 exhibit photochromism. Ab initio calculations show that the methoxy group in aldehydes 2 and 3 stabilizes the (E)-enols via O-H...O hydrogen bonding as compared to those of 1 by 5-6 kcal/mol relative to their corresponding benzocyclobutenols. Thus, the presence of methoxy and halo groups at position 2 serves not only to direct the formyl oxygen toward the methyl group for H-abstraction but also to stabilize the (E)-enols.
