Tetramethyl thiourea/Co2(CO)8-catalyzed Pauson-Khand reaction under balloon pressure of CO.

Org Lett

Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, College of Chemistry, and Laboratory of Chemical Genetics, ShenZhen Graduate School, Peking University, Beijing 100871, China.

Published: February 2005

A Pauson-Khand type of conversion of enynes to bicyclic cyclopentenones employing the commercially available Co2(CO)8 and tetramethylthiourea (TMTU) as catalysts is described. This method allows a variety of enynes with diverse functional groups to be cyclized into cyclopentenones of interest. [reaction: see text]

Download full-text PDF

Source
http://dx.doi.org/10.1021/ol047651aDOI Listing

Publication Analysis

Top Keywords

tetramethyl thiourea/co2co8-catalyzed
4
thiourea/co2co8-catalyzed pauson-khand
4
pauson-khand reaction
4
reaction balloon
4
balloon pressure
4
pressure pauson-khand
4
pauson-khand type
4
type conversion
4
conversion enynes
4
enynes bicyclic
4

Similar Publications

Developing a robust method integrating with selective membrane-based preconcentration and signal amplification for field virus detection.

Anal Chim Acta

October 2022

State Key Laboratory of Biocontrol, School of Life Sciences, Sun Yat-Sen University, Guangzhou, 510275, China; Institute of Environmental and Ecological Engineering, Guangdong University of Technology, Guangzhou, 510006, China; School of Biomedical and Pharmaceutical Sciences, Guangdong University of Technology, Guangzhou, 510006, China. Electronic address:

Infectious diseases caused by viruses have attracted global concern owing to their rapid spread and catastrophic consequences. Therefore, developing fast and reliable on-site virus detection methods is essential for the prevention and treatment of virus-related diseases. In this study, immunoassays on a membrane, combining virus preconcentration with nanoparticle-based signal amplification, were used to realize the rapid and accurate visual detection of viruses.

View Article and Find Full Text PDF

SHetA2 (NSC 721689), our lead Flex-Het anti-cancer agent, consists of a thiochroman (Ring A) and a 4-nitrophenyl (Ring B) linked by a thiourea bridge. In this work, several series of new analogs having a tetrahydroquinoline (THQ, Ring A) unit connected by a urea or thiourea linker to a 4-substituted phenyl (Ring B) have been prepared and evaluated relative to SHetA2 in terms of binding affinity with mortalin and inhibition of A2780 ovarian cancer cells. Six of the derivatives equaled or exceeded the efficacy shown by SHetA2.

View Article and Find Full Text PDF

Flexible heteroarotinoids (Flex-Hets) are compounds with promising anti-cancer activities. SHetA2, a first-generation Flex-Het, has been shown to inhibit the growth of cervical, head and neck, kidney, lung, ovarian, prostate, and breast cancers. However, SHetA2's high lipophilicity, limited selectivity, low oral bioavailability, and complicated synthesis has led to the development of second-generation compounds, such as 1-(1-(naphthalen-1-yl)ethyl)-3-(4-nitrophenyl) thiourea or SL-1-09.

View Article and Find Full Text PDF

A series of Flexible Heteroarotinoid (Flex-Het) analogs was synthesized and their biological activities were evaluated against the A2780 ovarian cancer cell line. The objective of this study was to establish structure-activity relationships (SARs) for new Flex-Het derivatives, which were previously inaccessible due to the limited availability of aryl isothiocyanate precursors. The current work developed a synthesis of isothiocyanate 13 and used it to prepare 14 diverse thiourea analogs of the lead compound SHetA2 (1, NSC-721689) from a range of commercial amines.

View Article and Find Full Text PDF

Novel flexible heteroarotinoid, SL-1-39, inhibits HER2-positive breast cancer cell proliferation by promoting lysosomal degradation of HER2.

Cancer Lett

February 2019

Department of Natural Sciences and Mathematics, Dominican University of California, 50 Acacia Avenue, San Rafael, CA, 94901, USA; College of Pharmacy, Touro University California, 1310 Club Drive, Vallejo, CA, 94594, USA. Electronic address:

SL-1-39 [1-(4-chloro-3-methylphenyl)-3-(4-nitrophenyl)thiourea] is a new flexible heteroarotinoid (Flex-Het) analog derived from the parental compound, SHetA2, previously shown to inhibit cell growth across multiple cancer types. The current study aims to determine growth inhibitory effects of SL-1-39 across the different subtypes of breast cancer cells and delineate its molecular mechanism. Our results demonstrate that while SL-1-39 blocks cell proliferation of all breast cancer subtypes tested, it has the highest efficacy against HER2+ breast cancer cells.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!