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Design, synthesis and pharmacological tests of leukotrienes A4 hydrolase inhibitors as potential targets of interest in cancer t - Literature review Example

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Design, synthesis and pharmacological tests of leukotrienes A4 hydrolase inhibitors as potential targets of interest in cancer treatment. Experimental Part (E)-Resveratrol is a naturally occurring, potent LTA4 hydrolase inhibitor of high medical importance…
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Design, synthesis and pharmacological tests of leukotrienes A4 hydrolase inhibitors as potential targets of interest in cancer t
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Download file to see previous pages Therefore, many synthetic pathways were developed to synthesize this highly promising compound. (Farina, Guiso, and Marra, 2002). One of the most efficient ways to achieve (E)-resveratrol is by employing the Heck reaction. The process is highly advantageous as it produces only the desired product in exceptional 99% yield: Scheme 1: Synthesis of (E)-resveratrol using Heck reaction As it is seen on the scheme 1, the starting 3,5-diacetoxy-stirene (1) was coupled with the para-iododerivative (2). Deacetilation of the formed stilbene derivative afforded the desired isomer of resveratrol. The starting material (1) was prepared through the Wittig reaction followed by subsequent acetylation of the produced phenol as can be illustrated on the following diagram. Scheme 2: Preparation of 3,5-diacetoxy-stirene (1) While addressing on the topic of trans-resveratrol, the research does not make any contribution in the area of cis-resveratrol synthesis and application. (Farina, Guiso, and Marra, 2002). To fill that gap, it is worth mentioning other methods of resveratrol synthesis. For example, Roberti, et al. (2003) synthesised a series of cis- and trans-resveratrol (Scheme 3) derivatives using the following Wittig reaction. Scheme 3: Synthesis of stilbene derivatives The groups marked as “R” are both silicon and carbon containing ethers. ...
Scheme 4: Highly promising cis-Resveratrol derivatives Comparing the accumulated results the authors concluded that structural changes in the stilbene backbone will undeniably lead to the production of powerful apoptosis-reducing agents. The described research takes the concept of resveratrol based drugs to a new level, but do not mention the poor stability of cis-resveratrol (4). The information about cis-resveratrol is not as abundant as it is for trans isomer. Cis-resveratrol has shown antioxidant proterties, antiplatelet properties and affect cytoplasmic calcium levels in vascular smooth muscle cells Cis-resveratrol (4) has also shown to inhibit kinase activity, a factor related to cancer (Jayatilake et al., 1993) and has a significant modulatory effect on the nuclear factor kappa B signaling pathway (Leiro et al, 2005) and, consequently, an important antioxidant role that may partially explain the cardioprotective effects attributed to long-term moderate red wine consumption. That was the main reason for our design of a cis-resveratrol analogue (5) by modulative pharmacomodulation. (Scheme 5). Scheme 5: cis-resveratrol (4) and its analogue (5) produced by modulative pharmacomodulation. The compound preserves cis-resveratrol’s essential structural requirements and does not have the possibility of isomerization like it happens with natural cis-resveratrol (Trela and Waterhouse, 1996). For the synthesis of the resveratrol analogue (5), we need to prepare the corresponding nitro derivative (6) from the respective aldehyde (7) using the methodology developed by Dauzone (1986) as described in scheme 6. Scheme 6 In order to prepare compound 5 we need to perform the ...Download file to see next pagesRead More
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