42134-54-3Relevant academic research and scientific papers
Mechanistic Insight on the Mode of Action of Colletoic Acid
Ling, Taotao,Miller, Darcie J.,Lang, Walter H.,Griffith, Elizabeth,Rodriguez-Cortes, Adaris,El Ayachi, Ikbale,Palacios, Gustavo,Min, Jaeki,Miranda-Carboni, Gustavo,Lee, Richard E.,Rivas, Fatima
supporting information, p. 6925 - 6940 (2019/08/20)
The natural product colletoic acid (CA) is a selective inhibitor of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1), which primarily converts cortisone to the active glucocorticoid (GC) cortisol. Here, CA's mode of action and its potential as a chemical tool to study intracellular GC signaling in adipogenesis are disclosed. 11β-HSD1 biochemical studies of CA indicated that its functional groups at C-1, C-4, and C-9 were important for enzymatic activity; an X-ray crystal structure of 11β-HSD1 bound to CA at 2.6 ? resolution revealed the nature of those interactions, namely, a close-fitting and favorable interactions between the constrained CA spirocycle and the catalytic triad of 11β-HSD1. Structure-activity relationship studies culminated in the development of a superior CA analogue with improved target engagement. Furthermore, we demonstrate that CA selectively inhibits preadipocyte differentiation through 11β-HSD1 inhibition, suppressing other relevant key drivers of adipogenesis (i.e., PPARγ, PGC-1α), presumably by negatively modulating the glucocorticoid signaling pathway. The combined findings provide an in-depth evaluation of the mode of action of CA and its potential as a tool compound to study adipose tissue and its implications in metabolic syndrome.
Neutral Organic Super Electron Donors Made Catalytic
Rohrbach, Simon,Shah, Rushabh S.,Tuttle, Tell,Murphy, John A.
supporting information, p. 11454 - 11458 (2019/07/18)
Neutral organic super electron donors (SEDs) display impressive reducing power but, until now, it has not been possible to use them catalytically in radical chain reactions. This is because, following electron transfer, these donors form persistent radical cations that trap substrate-derived radicals. This paper unlocks a conceptually new approach to super electron donors that overcomes this issue, leading to the first catalytic neutral organic super electron donor.
Iron-Catalyzed Coupling of Propargyl Bromides and Alkyl Grignard Reagents
Domingo-Legarda, Pablo,Soler-Yanes, Rita,Quirós-López, M. Teresa,Bu?uel, Elena,Cárdenas, Diego J.
supporting information, p. 4900 - 4904 (2018/09/10)
An iron-catalyzed Kumada-type cross-coupling reaction of propargyl halides with alkylmagnesium reagents is described. The reaction is fast, takes place in smooth conditions, tolerates several functional groups that would be able to react with the Grignard reagent, and may afford either allene or propargyl coupling derivatives. Factors involved in the observed regioselectivity have been studied.
Nickel(II)-Catalyzed Asymmetric Propargyl [2,3] Wittig Rearrangement of Oxindole Derivatives: A Chiral Amplification Effect
Xu, Xi,Zhang, Jianlin,Dong, Shunxi,Lin, Lili,Lin, Xiaobin,Liu, Xiaohua,Feng, Xiaoming
supporting information, p. 8734 - 8738 (2018/07/14)
A highly enantioselective [2,3] Wittig rearrangement of oxindole derivatives was realized by using a chiral N,N′-dioxide/NiII complex as the catalyst under mild reaction conditions. A strong chiral amplification effect was observed, and allowed access to chiral 3-hydroxy 3-substituted oxindoles bearing allenyl groups in high yields and enantioselectivities (up to 92 % ee) by using a ligand with only 15 % ee. A reasonable explanation was given based on the experimental investigations and X-ray crystal structures of enantiomerically pure and racemic catalysts. Moreover, the first catalytic kinetic resolution of racemic oxindole derivatives by a [2,3] Wittig rearrangement was realized with high efficiency and stereoselectivity.
Chemoproteomics-Enabled Discovery of a Potent and Selective Inhibitor of the DNA Repair Protein MGMT
Wang, Chao,Abegg, Daniel,Hoch, Dominic G.,Adibekian, Alexander
supporting information, p. 2911 - 2915 (2016/02/27)
We present a novel chemical scaffold for cysteine-reactive covalent inhibitors. Chloromethyl triazoles (CMTs) are readily accessed in only two chemical steps, thus enabling the rapid optimization of the pharmacological properties of these inhibitors. We d
Gold(I)-Catalyzed Angle Strain Controlled Strategy to Furopyran Derivatives from Propargyl Vinyl Ethers: Insight into the Regioselectivity of Cycloisomerization
Jin, Shengfei,Jiang, Chongguo,Peng, Xiaoshi,Shan, Chunhui,Cui, Shanshan,Niu, Yuanyuan,Liu, Yang,Lan, Yu,Liu, Yongxiang,Cheng, Maosheng
supporting information, p. 680 - 683 (2016/03/01)
A unique strategy for the regiospecific synthesis of bicyclic furopyran derivatives has been developed via a gold(I)-catalyzed propargyl-Claisen rearrangement/6-endo-trig cyclization of propargyl vinyl ethers. The introduction of angle strain into the substrates significantly altered the reaction's regioselectivity. Insight into the regioselectivity of the cycloisomerization was obtained with density functional theory calculations. (Chemical Equation).
Benzannulation of triynes to generate functionalized arenes by spontaneous incorporation of nucleophiles
Karmakar, Rajdip,Yun, Sang Young,Chen, Jiajia,Xia, Yuanzhi,Lee, Daesung
, p. 6582 - 6586 (2015/06/02)
The thermal reaction of ester-tethered 1,3,8-triynes provides novel benzannulation products with concomitant incorporation of a nucleophile. Evidence suggests that this reaction proceeds via an allene-enyne intermediate generated by an Alder-ene reaction in the first step. Depending on the substituent of the alkyne moiety on the allene-enyne intermediate, the subsequent transformation can take one of two different paths, each leading to discrete aromatization products. The benzannulation of a silane-substituted 1,3,8-triynes provides arene products with a nucleophile incorporated onto the newly formed benzene core, whereas an aryl substituent leads to nucleophile trapping at the benzylic carbon atom connected to the aryl substituent. The formation of these two different products results from the involvement of two regioisomeric allene-enyne intermediates.
Copper(i) iodide catalyzed synthesis of primary propargylic alcohols from terminal alkyne
Kundu, Shrishnu Kumar,Mitra, Kanchan,Majee, Adinath
, p. 13220 - 13223 (2015/02/19)
A highly efficient and practical method for the synthesis of primary propargylic alcohols has been developed using CuI as catalyst and paraformaldehyde as the formaldehyde source. The reaction was performed under mild reaction conditions offering the desired products in good to excellent yields with a variety of terminal alkynes.
Copper-catalyzed enantioselective allylic substitution with alkylboranes
Shido, Yoshinori,Yoshida, Mika,Tanabe, Masahito,Ohmiya, Hirohisa,Sawamura, Masaya
supporting information, p. 18573 - 18576 (2013/01/15)
The first catalytic enantioselective allylic substitution reaction with alkylboron compounds has been achieved. The reaction between alkyl-9-BBN reagents and primary allylic chlorides proceeded with excellent γ-selectivities and high enantioselectivities under catalysis of a Cu(I)-DTBM-SEGPHOS system. The protocol produces terminal alkenes with an allylic stereogenic center branched with functionalized sp3-alkyl groups. The reaction with a γ-silicon-substituted allyl chloride affords an efficient strategy for the enantioselective synthesis of functionalized α-stereogenic chiral allylsilanes.
A highly reusable rhodium catalyst-organic framework for the intramolecular cycloisomerization of 1,6-enynes
Corkum, Elizabeth G.,Hass, Michael J.,Sullivan, Andrew D.,Bergens, Steven H.
supporting information; experimental part, p. 3522 - 3525 (2011/09/16)
The intramolecular cycloisomerization of 1,6-enynes in 95-99% ee is reported using an immobilized Rh catalyst-organic framework synthesized from alternating ring-opening metathesis polymerization (altROMP) assembly. The framework was reused up to seven times, and it was used in high turnover number (TON) batch reactions. The catalyst provided the highest TONs to date (up to 890) for the cycloisomerizations, with catalyst loadings ranging from 0.2 to 0.06 mol %.
