A new anti-tubulin agent containing the benzo[b]thiophene ring system

Pinney, Kevin G.; Bounds, A. Dawn; Dingeman, Koren M.; Mocharla, Vani P.; Pettit, George R.; Bai, Ruoli; Hamel, Ernest

doi:10.1016/s0960-894x(99)00143-2

Cited by 121 publications

(83 citation statements)

References 28 publications

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“…We are currently investigating further biological studies of the synthesized compounds 2. Benzo [b]thiophene skeletons are an important class of S-heterocycles [15][16][17][18] and are found in a variety of drugs, pesticides, and biologically active compounds that exhibit various interesting biological properties [19][20][21][22][23][24]. Diaryl ketone scaffolds are also important motifs in natural products and pharmaceuticals [25][26][27][28][29][30] (Figure 1).…”

Section: Scheme 2 Proposed Redox Cyclesmentioning

confidence: 99%

Palladium(II) Catalyzed Cyclization-Carbonylation-Cyclization Coupling Reaction of (ortho-Alkynyl Phenyl) (Methoxymethyl) Sulfides Using Molecular Oxygen as the Terminal Oxidant

et al. 2016

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Section: Scheme 2 Proposed Redox Cyclesmentioning

confidence: 99%

Palladium(II) Catalyzed Cyclization-Carbonylation-Cyclization Coupling Reaction of (ortho-Alkynyl Phenyl) (Methoxymethyl) Sulfides Using Molecular Oxygen as the Terminal Oxidant

et al. 2016

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“…By the same token, a series of cis-restricted five-and six-membered fused heteroaromatic system bridgehead analogues including indoles 79-80 [93,94], benzofuran 81 [94], and benzothiophene 82 [95] were also designed as CA-4 mimics (Fig. 18).…”

Section: (D) Five-and Six-membered Fused Heteroaromatic System Bridgementioning

confidence: 99%

“…In 1999, Pinney et al [95] at Baylor University discovered a series of benzothiophenes exhibiting antitubulin activity by an approach utilizing the raloxifene skeleton (97) (a selective estrogen modulator) with its 2-aryl and 3-benzoyl parts mimicking ring A and ring B of CA-4, respectively (Fig. 24).…”

Section: (B) α β-Unsaturated Ketone Bridgehead Analoguesmentioning

confidence: 99%

Pharmaceutical Design of Antimitotic Agents Based on Combretastatins

Hsieh

Liou²,

Mahindroo

2005

CPD

149

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The design of novel anticancer agents based on the combretastatins, a group of antimitotic agents isolated from the bark of the South African willow tree Combretum caffrum Kuntz, is of considerable contemporary interest. Combretastatin A-4, the most active compound in the group, due to its unique dual features of antitubulin and antivascular properties, has drawn significant attention of medicinal chemists for the design of analogues as novel antitumor agents. To date, 252 references have been published since 1982 and 187 references have been published since 1998 related to combretastatins research. The 102 references related to chemistry efforts can be classified into three different categories including one-atom, two-atom, and three-atom bridgeheads as linker between two aryl rings of combretastatins. This review will particularly elucidate the rationale and strategic tactics towards the development of novel classes of antimitotic agents, based upon combretastatin A-4 as a promising lead.

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“…This drug arrested the growth of multidrug-sensitive cancer cells at the G 2 /M phase and induced apoptotic cell death in stationary phase cells at concentrations that do not impair the viability of normal nonproliferating cells [251]. Indanosine interacts with tubulin at the colchicine-binding site and inhibits tubulin polymerization with an IC 50 value equivalent to values obtained with podophyllotoxin and combretastatin A-4 [252]. The investigator suggested that indanosine and related indones may be considered as lead compounds for the development of chemotherapeutic strategies for drug-resistant malignancies.…”

Section: Indanosine (135)mentioning

confidence: 89%

Microtubulin Binding Sites as Target for Developing Anticancer Agents

Islam¹,

Iskander²

2004

MRMC

134

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Microtubules (MTs) play important and diverse roles in eukaryotic cells. Their function and biophysical properties have made alpha-and beta-tubulin, the main components of MTs, the subject of intense study. Interfering with normal MT dynamics, for example, by the addition of tubulin ligands, can cause the cell great distress and affect MT stability and functions, including mitosis, cell motion and intracellular organelle transport. It has been shown in the literature that tubulin is an important target molecule for developing anticancer drugs. Tubulin binding molecules have generated considerable interest after the successful introduction of the taxanes into clinical oncology and the widespread use of the vinca alkaloids vincristine and vinblastine. These compounds inhibit cell mitosis by binding to the protein tubulin in the mitotic spindle and preventing polymerization into the MTs. This mode of action is also shared with other natural agents eg colchicine and podophyllotoxin. However various tubulin isotypes have shown resistance to taxanes and other MT agents. Therefore, there is a strong need to design and develop new natural analogs as antimitotic agents to interact with tubulin at sites different from those of vinca alkaloids and taxanes. This minireview provides SAR on several classes of antimitotic agents reported in the literature. The structures and data given are essential to the scientists who are involved in drug design and development in the field of anticancer drugs.

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A new anti-tubulin agent containing the benzo[b]thiophene ring system

Cited by 121 publications

References 28 publications

Palladium(II) Catalyzed Cyclization-Carbonylation-Cyclization Coupling Reaction of (ortho-Alkynyl Phenyl) (Methoxymethyl) Sulfides Using Molecular Oxygen as the Terminal Oxidant

Palladium(II) Catalyzed Cyclization-Carbonylation-Cyclization Coupling Reaction of (ortho-Alkynyl Phenyl) (Methoxymethyl) Sulfides Using Molecular Oxygen as the Terminal Oxidant

Pharmaceutical Design of Antimitotic Agents Based on Combretastatins

Microtubulin Binding Sites as Target for Developing Anticancer Agents

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