14367-28-3Relevant academic research and scientific papers
Bis-glycinato complexes of palladium(II): Synthesis, structural determination, and hydrogen bonding interactions
Hobart Jr., David B.,Berg, Michael A.G.,Merola, Joseph S.
, p. 21 - 30 (2014)
Palladium(II) acetate and palladium(II) chloride react with glycine and glycine derivatives in acetone/water to yield square planar bis-chelated palladium amino acid complexes. Glycine, N-methylglycine and N,N-dimethylglycine all adopt the trans configuration when prepared from palladium(II) acetate, whereas glycine adopts a cis configuration when prepared from palladium(II) chloride. The crystal structures of all four complexes were obtained. The extended lattice structures arise from N-H··O or O··(HOH)··O hydrogen bonding. Nuclear magnetic resonance, infrared, high resolution mass spectroscopy, and UV-Vis spectroscopic data are evaluated.
Divergent Synthetic Access to E- and Z-Stereodefined All-Carbon-Substituted Olefin Scaffolds: Application to Parallel Synthesis of (E)- and (Z)-Tamoxifens
Ashida, Yuichiro,Honda, Atsushi,Sato, Yuka,Nakatsuji, Hidefumi,Tanabe, Yoo
, p. 73 - 89 (2017/02/10)
A highly substrate-general synthesis of all-carbon-substituted E- and Z-stereodefined olefins is performed. The method comprises two sets of parallel and stereocomplementary preparations of (E)- and (Z)-α,β-unsaturated esters involving two robust and distinctive reactions: 1) stereocomplementary enol tosylations using readily available TsCl/diamine/(LiCl) base reagents, and 2) stereoretentive Negishi cross-coupling using the catalysts [Pd(dppe)Cl2] (for E) and [Pd(dppb)Cl2] (for Z). The present parallel approach is categorized as both type I (convergent approach: 16 examples, 56–87 % yield) and type II (divergent approach: 18 examples, 70–95 % yield). The obtained (E)- and (Z)-α,β-unsaturated ester scaffolds are successfully transformed into various E- and Z-stereodefined known and novel olefins (8×2 derivatization arrays). As a demonstration, application to the parallel synthesis of both (E)- and (Z)-tamoxifens, a representative motif of all-carbon-substituted olefins, is accomplished in a total of eight steps with an overall yield of 58 % (average 93 %) and 57 % (average 93 %), respectively.
(E)- and (Z)-stereodefined enol phosphonates derived from β-ketoesters: Stereocomplementary synthesis of fully-substituted α,β-unsaturated esters
Nakatsuji, Hidefumi,Ashida, Yuichiro,Hori, Hiroshi,Sato, Yuka,Honda, Atsushi,Taira, Mayu,Tanabe, Yoo
, p. 8205 - 8210 (2015/08/03)
A versatile, robust, and stereocomplementary synthesis of fully-substituted (E)- and (Z)-stereodefined α,β-unsaturated esters 3 from accessible α-substituted β-ketoesters 1via (E)- and (Z)-enol phosphonates was achieved. The present method involves two ac
TRANSITION METAL COMPLEXES OF AMINO ACIDS AND RELATED LIGANDS AND THEIR USE AS CATALYSTS, ANTI-MICROBIALS, AND ANTI-CANCER AGENTS
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Paragraph 0260, (2013/04/24)
The present invention relates to the fields of chemistry and pharmaceuticals. Embodiments of the present invention provide transition metal complexes of amino acids. Transition metal complexes of embodiments of the invention according to Categories I, II, III, and/or IV may be used as antimicrobial, anti-malarial, and anti-cancer agents, as well as catalysts in chemical reactions. Such compounds of the invention are particularly useful for combating multi-drug resistance against a broad range of microbials (such as MRSA and mycobacteria), including gram positive and gram negative bacteria, as well as can be used as anti-cancer agents against bladder cancer, breast cancer, colon cancer, rectal cancer, endometrial cancer, kidney cancer, leukemia, lung cancer, melanoma, non-Hodgkin's lymphoma, pancreatic cancer, prostate cancer, and thyroid cancer, to name a few.
Key structural features of cis-cinnamic acid as an allelochemical
Abe, Masato,Nishikawa, Keisuke,Okuda, Katsuhiro,Shindo, Mitsuru,Fukuda, Hiroshi,Nakanishi, Kazunari,Tazawa, Yuta,Taniguchi, Tomoya,Park, So-Young,Hiradate, Syuntaro,Fujii, Yoshiharu
, p. 56 - 67,12 (2012/12/12)
1-O-cis-cinnamoyl-β-d-glucopyranose is one of the most potent allelochemicals isolated from Spiraea thunbergii Sieb. It is suggested that it derives its strong inhibitory activity from cis-cinnamic acid, which is crucial for phytotoxicity. It was synthesized to confirm its structure and bioactivity, and also a series of cis-cinnamic acid analogues were prepared to elucidate the key features of cis-cinnamic acid for lettuce root growth inhibition. The cis-cyclopropyl analogue showed potent inhibitory activity while the saturated and alkyne analogues proved to be inactive, demonstrating the importance of the cis-double bond. Moreover, the aromatic ring could not be replaced with a saturated ring. However, the 1,3-dienylcyclohexene analogue showed strong activity. These results suggest that the geometry of the C-C double bond between the carboxyl group and the aromatic ring is essential for potent inhibitory activity. In addition, using several light sources, the photostability of the cinnamic acid derivatives and the role of the C-C double bond were also investigated.
Stereoselective olefination of unfunctionalized ketones via ynolates
Shindo, Mitsuru,Sato, Yusuke,Yoshikawa, Takashi,Koretsune, Ryoko,Shishido, Kozo
, p. 3912 - 3916 (2007/10/03)
Ynolates react with ketones at room temperature to afford α,β,β,-trisubstituted acrylates (tetra-substituted olefins) with 2:1-8:1 geometrical selectivities. This can be regarded as a new olefination reaction of ketones giving tetrasubstituted olefins in good yield, even in the case of sterically hindered substrates. The reaction mechanism involves cycloaddition of ynolates with a carbonyl group and subsequent thermal electrocyclic ring-opening of the resulting β-lactone enolates. The stereoselectivity is determined in the ring-opening, which is regulated by torquoselectivity. In this paper, we describe the scope and limitations of olefination of ketones via ynolates and discuss the stereocontrol mechanism.
Stereoselective synthesis of tetrasubstituted (Z)-alkenes from aryl alkyl ketones utilizing the Horner-Wadsworth-Emmons reaction
Sano, Shigeki,Takehisa, Tomoka,Ogawa, Shiho,Yokoyama, Kenji,Nagao, Yoshimitsu
, p. 1300 - 1302 (2007/10/03)
Tetrasubstituted (Z)-alkenes were readily prepared through the Horner-Wadsworth-Emmons reactions of methyl 2-[bis(2,2,2-trifluoroethyl) phosphono]propionate with aryl alkyl ketones by employing Sn(OSO 2CF3)2 and N-ethylpiperidine.
