Total synthesis of Epothilone E and related side-chain modified analogues via a stille coupling based strategy1This paper is dedicated with admiration and respect to the memory of Sir Derek H. R. Barton.1

Nicolaou, K. C.; King, N. Paul; Finlay, M. Ray V.; He, Yan; Roschangar, Frank; Vourloumis, Dionisios; Vallberg, Hans; Sarabia, Francisco; Ninkovic, Sacha; Hepworth, David

doi:10.1016/s0968-0896(98)00153-9

Cited by 87 publications

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“…[116,153] (For the use of vinyl iodide 80 (Scheme 9) in the synthesis of C26 and side-chain-modified analogues, see ref. [157]. )…”

Section: Side Chain Modificationsmentioning

confidence: 98%

“…Therefore, it is not surprising that this part of the epothilone structure has been heavily targeted for SAR studies. Modifications of the epothilone side chain include the replacement of the thiazole ring by other heterocyclic structures [109,110,152] or simple phenyl groups, [109,153] modifications at the 2-and 4-positions of the thiazole ring, [110,114,[154][155][156][157] and the synthesis of C16-desmethyl Epo B. [153,158] These studies have shown, for example, that an oxazole ring can be substituted for the natural thiazole heterocycle without any loss in biological potency [109,110] or that the removal of the allylic methyl group at C16 leads to only a minor decrease in activity.…”

Section: Side Chain Modificationsmentioning

confidence: 99%

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The Chemistry and Biology of Epothilones—The Wheel Keeps Turning

et al. 2007

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Epothilones have captured the attention of chemists, biologists, and drug researchers ever since they were found to inhibit human cancer cell growth through a “taxol‐like” mechanism over ten years ago. Today, at least seven epothilone‐derived agents have entered clinical trials. However, additional new and exciting analogues have emerged in recent years, suggesting that the potential of these natural products to serve as leads for new anticancer drugs is far from exhausted.

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“…[116,153] (For the use of vinyl iodide 80 (Scheme 9) in the synthesis of C26 and side-chain-modified analogues, see ref. [157]. )…”

Section: Side Chain Modificationsmentioning

confidence: 98%

Section: Side Chain Modificationsmentioning

confidence: 99%

The Chemistry and Biology of Epothilones—The Wheel Keeps Turning

et al. 2007

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“…The role of the thiazole is already exhibited by most epotilones used against multi-drug resistant tumor [5] and treatment of type 2 diabetes [6]. Organic non-linear optics (NLO) materials formed by a donor-acceptor pair in their molecular system exhibit noteworthy NLO characteristics [7].…”

Section: Commentmentioning

confidence: 99%

Crystal structure of (E)-N,N-diethyl-2-(5-nitrothiazol-2-yl)-1-phenylethen-1-amine, C₁₅H₁₇N₃O₂S

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et al. 2017

Zeitschrift Für Kristallographie - New Crystal Structures

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CCDC no.: 1558756The title crystal structure is shown in the figure. conditions. Table 2 lists the atoms with their coordinates and displacement parameters. Source of materialsThe title compound was synthesized from the Sonogashira Coupling-Aminovinylation Sequence reaction [4]. In a nitrogen atmosphere, a THF solution of phenylacetylene (1.1 mmol in 5 mL THF) was added dropwisely into a stirred mixture of 2-bromo-5-nitrothiazole (1 mmol), Pd(PPh 3 ) 2 Cl 2 (14 mg, 0.02 mmol), CuI (7 mg, 0.04 mmol), and 11 mL of THF/NEt 3 (10:1). The reaction mixture was stirred at room temperature overnight until conversion was complete (monitored by TLC). Then, a solution of diethylamine (2 mmol) in 5 mL of methanol was added, and the mixture was heated to reflux for ca. 9 hour until complete conversion (monitored by TLC). The solvents were evaporated in vacuo, and the residue was purified by chromatography over a short pad of aluminum oxide eluting with dichloromethane followed by acetone to yield 60% of the entitled compound. The residue was then recrystallized in dichloromethane by evaporation in vacuo, which yielded dark red crystals. After several attempts a suitable crystal for single X-ray diffraction study was obtained. Experimental detailsH atoms were fixed geometrically at ideal positions and allowed to ride on the parent atoms with C-H = 0.93-0.97 Å, with U iso (H) = 1.5Ueq(C) (for CH 3 )and 1.2 Ueq(C) (for CH 2 and CH).

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“…Based on Hantzsch concept, some newer methods, such as cycloaddition of tosylmethyl isocyanide to thione derivatives (Bergstrom et al, 1994), oxidation of thiazoline and thiazolidine ring systems (Martin & Hu, 1999), the Ugi reaction (Kazmaier & Ackermann, 2005) and others (Mustafa et al, 2004), have been developed. Other methodologies developed include Pd-mediated coupling process (Sapountzis et al, 2005;Lipshutz et al, 2004;Nicolaou et al, 1999), nucleophilic reactions of Lithiothiazoles (Dondoni, 1998), solid supported synthesis to generate small organic molecule libraries (Kazzouli et al, 2002) and solution phase preparation of 2-aminothiazole combinatorial libraries (Bailey et al, 1996). Many of these synthetic methods involve the use of hazardous organic solvents, high temperatures, longer reaction times or lower yields.…”

Section: Thiazolesmentioning

confidence: 99%