- MC - 1568 Synthesis method
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The invention provides a synthesis method of MC-1568. The preparation method comprises the steps as follows: step 1, tetrahydrofuran, triethyl phosphonoacetate and potassium tert-butoxide are stirredat the room temperature, a suspension of N-methylpyrrole-2-formaldehyde and tetrahydrofuran is added, the reaction solution is stirred, water is added after the reaction, ethyl acetate is added, the mixed solution is stirred and left to stand for layering, a water layer is extracted with ethyl acetate, and an organic phase is distilled under pressure; step 2, (E)-3-(5-formyl-1-methyl-1H-pyrrole-2-yl)ethyl acrylate is synthesized; step 3, a compound 5 is synthesized; step 4, a compound 6 is synthesized; step 5, MC-1568 is synthesized. By means of the synthesis method, purification in traditional technologies is avoided, and industrialization can be realized.
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Paragraph 0012; 0014-0015
(2021/08/07)
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- COMPOSITIONS AND METHODS FOR TREATING EPIGENETIC DISEASE
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The present disclosure provides compounds and compositions capable of treating cancer or an autoimmune disease, such as Crohn's disease, and methods of use thereof.
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Page/Page column 29-30
(2020/02/16)
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- NOVEL MACROCYCLIC DERIVATIVES, PROCESS FOR PREPARING SAME AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME
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Compound of formula (I): wherein A1, A2, Ra, Rb, Rc, Rd, R3, R4, X, Y and G are as defined in the description, and their use in the manufacture of medicaments.
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Paragraph 0343; 0344
(2020/08/25)
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- C?H Alkenylation of Pyrroles by Electronically Matching Ligand Control
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Directing group and substrate control strategies have frequently been employed for the regioselective C?H alkenylation of acid- and oxidant-sensitive pyrrole heterocycles. We developed an undirected, aerobic strategy for the C?H alkenylation of N-alkylpyrroles by ligand control. For C2-alkenylation of electron-rich N-alkylpyrroles, an electrophilic palladium catalyst derived from Pd(OAc)2 and 4,5-diazafluoren-9-one (DAF) was used. Alternatively, a combination of Pd(OAc)2 and a mono-protected amino acid ligand, Ac-Val-OH, was useful for C5-alkenylation of N-alkylpyrroles possessing electron-withdrawing groups at the C2 position. This approach based on the electronic effects of heterocycles and catalysts can rapidly provide a wide range of alkenyl pyrroles from readily available N-alkylpyrroles and alkenes.
- Kim, Hyun Tae,Lee, Woohyeong,Kim, Eunmin,Joo, Jung Min
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supporting information
p. 2418 - 2422
(2018/09/10)
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- Bioactivity and structure–activity relationship of cinnamic acid derivatives and its heteroaromatic ring analogues as potential high-efficient acaricides against Psoroptes cuniculi
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A series of cinnamic acid derivatives and its heteroaromatic ring analogues were synthesized and evaluated for acaricidal activity in vitro against Psoroptes cuniculi, a mange mite. Among them, eight compounds showed the higher activity with median lethal concentrations (LC50) of 0.36–1.07 mM (60.4–192.1 μg/mL) and great potential for the development of novel acaricidal agent. Compound 40 showed both the lowest LC50 value of 0.36 mM (60.4 μg/mL) and the smallest median lethal time (LT50) of 2.6 h at 4.5 mM, comparable with ivermectin [LC50 = 0.28 mM (247.4 μg/mL), LT50 = 8.9 h], an acaricidal drug standard. SAR analysis showed that the carbonyl group is crucial for the activity. The type and chain length of the alkoxy in the ester moiety and the steric hindrance near the ester group significantly influence the activity. The esters were more active than the corresponding thiol esters, amides, ketones or acids. Replacement of the phenyl group of cinnamic esters with α-pyridyl or α-furanyl significantly increase the activity. Thus, a series of cinnamic esters and its heteroaromatic ring analogues with excellent acaricidal activity emerged.
- Chen, Dong-Dong,Zhang, Bing-Yu,Liu, Xiu-Xiu,Li, Xing-Qiang,Yang, Xin-Juan,Zhou, Le
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supporting information
p. 1149 - 1153
(2018/03/05)
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- An efficient and general method for the heck and buchwald-hartwig coupling reactions of aryl chlorides
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The β-diketiminatophosphane Pd complex acted as a powerful catalyst for the Heck coupling of aryl chlorides with alkenes. Various aryl and heteroaryl chlorides were coupled efficiently under relatively mild conditions. Furthermore, this catalytic system also proved to be highly active in the Buchwald-Hartwig coupling of deactivated and sterically hindered aryl chlorides at room temperature.
- Lee, Dong-Hwan,Taher, Abu,Hossain, Shahin,Jin, Myung-Jong
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supporting information; experimental part
p. 5540 - 5543
(2011/12/15)
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- Preparation of Boc-protected cinnamyl-type alcohols: A comparison of the Suzuki-Miyaura coupling, cross-metathesis, and Horner-Wadsworth-Emmons approaches and their merit in parallel synthesis
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Three synthetic strategies for the construction of tert-butyl (E)-3-arylprop-2-en-1-ol carbonates are described. Complementary approaches employing Suzuki-Miyaura coupling and cross-metathesis reaction gave moderate yields of the title compounds in one-step, both methods are suitable for high-throughput and parallel chemistry. A detailed investigation into the Suzuki-Miyaura coupling reaction is provided along with the studies on the synthesis of pinacolyl 1-(tert-butyloxycarbonyl)propenol-3-ylboronate, the key building block. Conventional synthesis of the title compounds via the Horner-Wadsworth-Emmons reaction as a key step in a three-step-one-purification protocol was optimized and the results are compared with those of the latter reactions.
- Stambasky, Jan,Malkov, Andrei V.,Kocovsky, Pavel
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experimental part
p. 705 - 732
(2009/04/03)
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- Discovery of (Aryloxopropenyl)pyrrolyl Hydroxyamides as Selective Inhibitors of Class IIa Histone Deacetylase Homologue HD1-A
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Chemical manipulations performed on aroyl pyrrolyl hydroxyamides, a new class of HDAC inhibitors previously reported by us, led to (aryloxopropenyl)pyrrolyl hydroxyamides 3a-g. Such compounds, showing better inhibitory activity against maize HD1-A than HD
- Mai, Antonello,Massa, Silvio,Pezzi, Riccardo,Rotili, Dante,Loidl, Peter,Brosch, Gerald
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p. 4826 - 4829
(2007/10/03)
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- Barium Hydroxide as Catalyst in Organic Reactions; V. Application in the Horner Reaction under Solid-Liquid Phase-Transfer Conditions
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A new application of a barium hydroxide catalyst for the Horner reaction is described.The scope of the synthetic method is shown; furthermore, the yields are higher and the reaction times shorter than those previously reported for similar experimental conditions (solid-liquid).Ethyl 3-(1'-pyrenyl)-acrylate and the 3-(1'-pyrenyl)-acrylonitrile are described for the first time.
- Sinisterra, J. V.,Mouloungui, Z.,Delmas, M.,Gaset, A.
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p. 1097 - 1100
(2007/10/02)
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