149550-21-0Relevant articles and documents
Basic Ionic Liquid Promoted Domino Knoevenagel–Thia-Michael Reaction: An Efficient and Multicomponent Strategy for Synthesis of 1,3-Thiazines
Siddiqui,Rahila,Shamim, Shayna,Rai, Pragati,Shireen,Waseem, Malik A.,Srivastava, Arjita,Srivastava, Anjali
, p. 1284 - 1291 (2016)
An efficient, three-component strategy for synthesis of 1,3-thiazines with high atom economy in one-pot mediated by room temperature basic ionic liquid is described here. The strategy involves basic ionic liquid, [bmim]OH-catalyzed Knoevenagel condensatio
Solid superbase derived from lanthanum-magnesium composite oxide and its catalytic performance in the knoevenagel condensation under solvent-free condition
Wei, Yudan,Zhang, Shuguo,Yin, Shuangfeng,Zhao, Chang,Luo, Shenglian,Au, Chak-Tong
, p. 1333 - 1338 (2011)
We report for the first time the synthesis of a novel solid superbase that was derived from lanthanum-magnesium composite oxide and KOH through thermal treatment. The as-prepared material shows base strength (H-) above 26.5 and is a high-effici
Development of Novel Mitochondrial Pyruvate Carrier Inhibitors to Treat Hair Loss
Liu, Xiaoguang,Flores, Aimee A.,Situ, Lisa,Gu, Wen,Ding, Hui,Christofk, Heather R.,Lowry, William E.,Jung, Michael E.
, p. 2046 - 2063 (2021/02/16)
Herein, we report the synthesis and evaluation of novel analogues of UK-5099 both in vitro and in vivo for the development of mitochondrial pyruvate carrier (MPC) inhibitors to treat hair loss. A comprehensive understanding of the structure-activity relationship was obtained by varying four positions of the hit compound, namely, the alkyl group on the N1 position, substituents on the indole core, various aromatic and heteroaromatic core structures, and various Michael acceptors. The major discovery was that the inhibitors with a 3,5-bis(trifluoromethyl)benzyl group at the N1 position were shown to have much better activity than JXL001 (UK-5099) to increase cellular lactate production. Additionally, analogue JXL069, possessing a 7-azaindole heterocycle, was also shown to have significant MPC inhibition activity, which further increases the chemical space for drug design. Finally, more than 10 analogues were tested on shaved mice by topical treatment and promoted obvious hair growth on mice.
The Knoevenagel condensation using quinine as an organocatalyst under solvent-free conditions
Jain, Kavita,Chaudhuri, Saikat,Pal, Kuntal,Das, Kalpataru
supporting information, p. 1299 - 1304 (2019/01/21)
The Knoevenagel condensation between active methylene compounds and aromatic carobonyl compounds has been developed using quinine as an organocatalyst to afford various electrophilic alkenes in excellent yields (up to 90%). In the presence of a catalytic amount of quinine (15 mol%), the reaction proceeded at room temperature (RT) under solvent-free conditions. In this green approach, the organocatalyst was recovered and recycled for up to four cycles without appreciable loss of activity.
Kinetic insights of DNA/RNA segment salts catalyzed knoevenagel condensation reaction
Li, Weina,Fedosov, Sergey N.,Tan, Tianwei,Xu, Xuebing,Guo, Zheng
, p. 3294 - 3300 (2014/12/11)
In this work, we demonstrated that (i) salts of RNA/DNA segments were capable of catalyzing Knoevenagel condensation at physiological pH 7.0 with efficiency comparable to one of the best enzymes, porcine pancreatic lipase (PPL); and (ii) a broad scope of
Determination of thermodynamic affinities of various polar olefins as hydride, hydrogen atom, and electron acceptors in acetonitrile
Cao, Ying,Zhang, Song-Chen,Zhang, Min,Shen, Guang-Bin,Zhu, Xiao-Qing
, p. 7154 - 7168 (2013/08/23)
A series of 69 polar olefins with various typical structures (X) were synthesized and the thermodynamic affinities (defined in terms of the molar enthalpy changes or the standard redox potentials in this work) of the polar olefins obtaining hydride anions, hydrogen atoms, and electrons, the thermodynamic affinities of the radical anions of the polar olefins (X ?-) obtaining protons and hydrogen atoms, and the thermodynamic affinities of the hydrogen adducts of the polar olefins (XH?) obtaining electrons in acetonitrile were determined using titration calorimetry and electrochemical methods. The pure Ci - 'C π-bond heterolytic and homolytic dissociation energies of the polar olefins (X) in acetonitrile and the pure Ci - 'C π-bond homolytic dissociation energies of the radical anions of the polar olefins (X?-) in acetonitrile were estimated. The remote substituent effects on the six thermodynamic affinities of the polar olefins and their related reaction intermediates were examined using the Hammett linear free-energy relationships; the results show that the Hammett linear free-energy relationships all hold in the six chemical and electrochemical processes. The information disclosed in this work could not only supply a gap of the chemical thermodynamics of olefins as one class of very important organic unsaturated compounds but also strongly promote the fast development of the chemistry and applications of olefins.
One-pot multistep cascade reactions over multifunctional nanocomposites with pd nanoparticles supported on amine-modified mesoporous silica
Li, Ping,Liu, Hua,Yu, Yu,Cao, Chang-Yan,Song, Wei-Guo
, p. 2459 - 2465 (2013/10/08)
Two kinds of multifunctional nanocomposites, SBA-15-NH2/Pd-p and SBA-15-NH2/Pd-f, with platelet-like and fiber-like morphologies, respectively, were fabricated by immobilizing Pd NPs onto amine-functionalized SBA-15. Some of the amino groups acted as anchoring sites for Pd NPs, whilst the remaining groups acted as Bronsted basic sites. As a result, the composites served as excellent multifunctional heterogeneous catalysts for one-pot multistep cascade reaction sequences. Moreover,when diffusion was the rate-determine step, SBA-15-NH2/Pd-p, with small mesopores, was superior to the fiber-like control sample, owing to its short diffusion length, a lower possibility of pore clogging, and better mass transportation for the reaction species during the catalysis.
Organic amine grafting on mesoporous silica as a hybrid catalyst for heterogeneous three-component one-pot reaction
Komura, Kenichi,Mishima, Yuta,Koketsu, Mamoru
, p. 128 - 132 (2013/02/21)
The organic-inorganic hybrid catalyst was prepared by immobilizing 3-methylaminopropyl moiety onto mesoporous silica, MCM-41, and applied for solid base catalyst of three-component one-pot reaction, i.e. Knoevenagel condensation of aldehyde with the active methylene compound to yield an electron deficient alkene which is subjective to be reacted with nitromethane by Michael addition to form tri-substituted primary nitro compound. The catalyst was characterized by powder-XRD, TG-DTA, FT-IR, nitrogen adsorption-desorption measurement and solid-state cross polarization magic angle spinning (CP/MAS) NMR, and exhibited high catalytic activity in three-component one-pot reaction; however, with poor reusability.
Efficient asymmetric synthesis of 4H-chromene derivatives through a tandem michael addition-cyclization reaction catalyzed by a salen-cobalt(II) complex
Dong, Zhenhua,Liu, Xiaohua,Feng, Juhua,Wang, Min,Lin, Lili,Feng, Xiaoming
supporting information; experimental part, p. 137 - 142 (2011/03/18)
The asymmetric synthesis of 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromene derivatives was achieved through a tandem Michael addition-cyclization reaction of easily available cyclohexane-1,3-dione and ethyl 2-cyano-3-phenylacrylates. Moderate to good yields (up to 81%) and high enantioselectivities (up to 89%ee) were obtained with a chiral salen-cobalt(II) complex. This process was air tolerant and easily performed, which provides an efficient method for the synthesis of chiral 4H-chromene derivatives. The asymmetric synthesis of 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromene derivatives was achieved through a tandem Michael addition-cyclization reaction of easily available cyclohexane-1,3-dione and ethyl 2-cyano-3-phenylacrylates catalyzed by a chiral salen-cobalt(II) complex with moderate to good yields (up to 81%) and high enantioselectivities (up to 89%ee).
NITROGENATED HETEROCYCLIC COMPOUND AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME
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Page/Page column 26, (2008/12/06)
The present invention relates to novel compounds having a xanthine oxidase inhibitory effect and an uricosuric effect and pharmaceutical compositions comprising the same as an active ingredient. That is, the present invention relates nitrogen-containing heterocyclic compounds represented by the following general formula (I): wherein Y1 represents N or C(R4) ; Y2 represents N or C(R5) ; R4 and R5 independently represent an alkyl group, a hydrogen atom etc. ; one of R1 and R2 represents an optionally substituted aryl group, an alkoxygroup or an optionally substituted heterocyclic group; the other of R1 and R2 represents a haloalkyl group, a cyanogroup, ahalogenatometc.; and R3 represents a 5-tetrazolyl group or a carboxy group, and pharmaceutically acceptable salts thereof, and pharmaceutical compositions comprising the same as an active ingredient.
