New Approach to the Total Synthesis of (‐)‐Zeylenone from Shikimic Acid.

Zhang, Yi; Liu, An; Ye, Zu Guang; Lin, Jian; Xu, Lizhen; Yang, Shaofeng

doi:10.1002/chin.200714223

Cited by 2 publications

(2 citation statements)

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“…85 The shikimic acid-based synthesis of zeylenone is widely used as a preparation for chemotherapy in cancer patients. 86 Shikimic acid analogue skeleton is a constituent of several antitumor products. 87…”

Section: Brief Review Of Successful Leadsmentioning

confidence: 99%

The Structure-Based Virtual Screening for Natural Compounds that Bind with the Activating Receptors of Natural Killer Cells

2021

TJNPR

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Cancers are a group of diseases characterized by erratic cell growth which invade and spread into other parts of the body. 1,2 They are caused by DNA damage and an ineffective DNA repair mechanism. According to a 2015 WHO report, cancer is the second leading cause of death globally and there were 90.5 million incidences of cancer in 2015 which accounted for 8.8 million deaths. 3 Cancers are caused by a persistent damage to DNA which culminates into mutations of certain gene sequences in the human genome. 4 Expression of these mutant sequences lead to an autonomous and unregulated hyper-proliferation of cells; insufficient apoptosis; altered differentiation and metabolism; genomic instability; and immortalization. 5 The abnormal proliferation of cells is due to alterations in the cell cycle replication mechanism due to nuclear and cytoplasm distortions. These changes include hyperchromatism, increased telomerase expression, prominent nucleoli, irregular chromatin distribution within nuclei, and increased size of nucleus, pleomorphism, and chromosomal translocations. 6,7 Available cancer therapies such as chemotherapy are non-selective as other normal rapidly dividing cells (including immune cells) are destroyed. Another major frustration faced by clinicians and researchers includes the evasive nature of cancer cells as they beat the

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Section: Brief Review Of Successful Leadsmentioning

confidence: 99%

The Structure-Based Virtual Screening for Natural Compounds that Bind with the Activating Receptors of Natural Killer Cells

2021

TJNPR

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“…An improved route for the enantioselective synthesis of (-)-zeylenone from SA has been observed. 23 The 4-epi-shikimic acid skeleton is a constituent of several antitumor products, such as dioxolamycin, the cythiaformines B, C, D, and pericosine A. 24 Platinum (II) anticancer drugs are watersoluble complexes that retain antitumor activity and are effectively absorbed after oral administration; SA complexes of platinum (II) are active against L1210 and P388 leukemia and B16 melanoma in vivo.…”

Section: Antitumor Activitymentioning

confidence: 99%

Current perspectives on applications of shikimic and aminoshikimic acids in pharmaceutical chemistry

Quiroz¹,

Carmona²,

Bolívar³

et al. 2014

RRMC

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Aromatic metabolism comprises the shikimic acid (SA) and the aminoshikimic acid (ASA) pathways. The SA pathway is the common route for the biosynthesis of aromatic amino acids and other metabolites in bacteria, higher plants, fungi, and Apicomplexa parasites, but this pathway is absent in mammals. A variant of the SA pathway known as the ASA pathway branches off from the normal pathway in some bacteria, and its final product, 3-amino-5-hydroxybenzoic acid, is the precursor for many aminoglycoside antibiotics such as kanamycin, neomycin, butirosin, and spectinomycin. The SA pathway includes the key intermediate SA, which is the precursor for the chemical synthesis of the drug oseltamivir phosphate, known commercially as Tamiflu ® , an efficient inhibitor of the neuraminidase enzyme of the seasonal influenza viruses types A and B, avian influenza virus H5N1, and human influenza virus H1N1. Meanwhile, the intermediate of the ASA pathway, ASA, is an attractive candidate for use as the core scaffold for the synthesis of combinatorial libraries and is a potential alternative to SA as a precursor for oseltamivir phosphate synthesis. In this review, we discuss the relevance of the key intermediates SA and ASA as scaffold molecules for the synthesis of diverse chemicals. We highlight the current and potential pharmaceutical applications of these molecules and discuss the main strategies for the production of these aromatic compounds from natural sources and the application of metabolic engineering strategies in diverse bacterial strains for production through biotechnological processes.

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New Approach to the Total Synthesis of (‐)‐Zeylenone from Shikimic Acid.

Abstract: New Approach to the Total Synthesis of (-)-Zeylenone from Shikimic Acid. -The natural antitumor product (-)-zeylenone (I) is prepared for the first time in a stereoselective synthesis from shikimic acid. -(ZHANG, Y.; LIU, A.; YE, Z. G.; LIN, J.; XU*, L. Z.; YANG, S. L.; Chem.

Cited by 2 publications

References 1 publication

The Structure-Based Virtual Screening for Natural Compounds that Bind with the Activating Receptors of Natural Killer Cells

The Structure-Based Virtual Screening for Natural Compounds that Bind with the Activating Receptors of Natural Killer Cells

Current perspectives on applications of shikimic and aminoshikimic acids in pharmaceutical chemistry

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