55149-84-3Relevant articles and documents
EASILY DECOMPOSABLE LIGNIN GENERATOR
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, (2018/02/22)
PROBLEM TO BE SOLVED: To provide an easily decomposable lignin generator containing a compound that can be introduced to a structure of lignin and can make lignin easily decomposable. SOLUTION: The easily decomposable lignin generator contains a compound represented by general formula (1), where R1 to R3 are identical or different and each represent a hydrogen atom, alkoxy group or alkyl group, R4 represents an organic group, and n represents an integer from 0 to 3. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPO&INPIT
A simple route to polysubstituted indoles exploiting azide induced furan ring opening
Abaev, Vladimir T.,Plieva, Anastasiya T.,Chalikidi, Petrakis N.,Uchuskin, Maxim G.,Trushkov, Igor V.,Butin, Alexander V.
supporting information, p. 4150 - 4153 (2014/09/30)
A straightforward, efficient indole synthesis based on thermolysis of 2-(2-azidobenzyl)furans with attack of the formed nitrene moiety onto the ipso position of furan ring has been developed. The cyclization is accompanied by furan ring opening and affords indoles with a 2-acylvinyl substituent suitable for further modifications.
Synthesis and antitumor activity of feruloyl and caffeoyl derivatives This paper is dedicated to Prof. Wei-xiao Hu for his lifelong commitment to mentoring graduate students
Chen, Hui-Zhen,Chen, You-Bao,Lv, Ya-Ping,Zeng, Fang,Zhang, Juan,Zhou, Yong-Lie,Li, Han-Bing,Chen, Li-Fei,Zhou, Bin-Jie,Gao, Jian-Rong,Xia, Chun-Nian
supporting information, p. 4367 - 4371 (2015/02/06)
We developed two efficient protocols for the synthesis of feruloyl and caffeoyl derivatives from commercial vanillin and veratraldehyde. Pharmacological activities were assessed against a panel of human cancer cell lines in vitro. Most synthesized compounds demonstrated attractive cytotoxicity. Several new compounds demonstrated significant antiproliferative and cytotoxic activities against HeLa and Bewo tumor cell lines. In particular, 5-nitro caffeic adamantyl ester showed broad spectrum of tumor inhibition in 10 cell lines, and reduced tumor weight by 36.7% in vivo when administered at a dose of 40 mg kg-1.
HIV-1 integrase strand-transfer inhibitors: Design, synthesis and molecular modeling investigation
De Luca, Laura,De Grazia, Sara,Ferro, Stefania,Gitto, Rosaria,Christ, Frauke,Debyser, Zeger,Chimirri, Alba
supporting information; experimental part, p. 756 - 764 (2011/03/20)
This study is focused on a new series of benzylindole derivatives with various substituents at the benzene-fused ring, suggested by our 3D pharmacophore model developed for HIV-1 integrase inhibitors (INIs). All synthesized compounds proved to be active in the nanomolar range (6-35 nM) on the strand-transfer step (ST). In particular, derivative 4-[1-(4-fluorobenzyl)- 5,7-dimethoxy-1H-indol-3-yl]-2-hydroxy-4-oxobut-2-enoic acid (8e), presenting the highest best-fit value on pharmacophore model, showed a potency comparable to that of clinical INSTIs GS 9137 (1) and MK-0518 (2). The binding mode of our molecules has been investigated using the recently published crystal structure of the complex of full-length integrase from the prototype foamy virus in complex with its cognate DNA (PFV-IN/DNA). The results highlighted the ability of derivative 8e to assume the same binding mode of MK-0518 and GS 9137.
The synthetic and biological studies of discorhabdins and related compounds
Wada, Yasufumi,Harayama, Yu,Kamimura, Daigo,Yoshida, Masako,Shibata, Tomoyuki,Fujiwara, Kousaku,Morimoto, Koji,Fujioka, Hiromichi,Kita, Yasuyuki
, p. 4959 - 4976 (2011/08/06)
Various analogues of the marine alkaloids, discorhabdins, have been synthesized. The strategy contains spirocyclization with phenyliodine(iii) bis(trifluoroacetate) (PIFA), oxidative fragmentation of the β-amino alcohols with the hypervalent iodine reagent C6F 5I(OCOCF3)2, the detosylation and dehydrogenation reaction of the pyrroloiminoquinone unit in the presence of a catalytic amount of NaN3 and the bridged ether synthesis with HBr-AcOH as the key reactions. All the synthesized compounds were evaluated by in vitro MTT assay for cytotoxic activity against the human colon cancer cell line HCT-116. Furthermore, the discorhabdin A oxa analogues were also evaluated against four kinds of tumor model cells, a human colon cancer cell line (WiDr), a human prostate cancer cell line (DU-145) and murine leukemia cell lines (P388 and L1210). For the identification of the target, discorhabdin A and the discorhabdin A oxa analogue were evaluated by an HCC panel assay. In the test, discorhabdins could have a novel mode of action with the tumor cells. The Royal Society of Chemistry 2011.
Fluorinated cannabinoid CB2 receptor ligands: Synthesis and in vitro binding characteristics of 2-oxoquinoline derivatives
Turkman, Nashaat,Shavrin, Aleksander,Ivanov, Roman A.,Rabinovich, Brian,Volgin, Andrei,Gelovani, Juri G.,Alauddin, Mian M.
supporting information; experimental part, p. 5698 - 5707 (2011/10/13)
Cannabinoid receptor 2 (CB2) plays an important role in human physiology and the pathophysiology of different diseases, including neuroinflammation, neurodegeneration, and cancer. Several classes of CB2 receptor ligands, including 2-oxoquinoline derivatives, have been previously reported. We report the synthesis and results of in vitro receptor binding of a focused library of new fluorinated 2-oxoquinoline CB2 ligands. Twelve compounds, 13-16 18, 19, 21-24, 27, and 28 were synthesized in good yields in multiple steps. Human U87 glioma cells expressing either hCB1 (control) or hCB2 were generated via lentiviral transduction. In vitro competitive binding assay was performed using [3H]CP-55,940 in U87hCB1 and U87hCB2 cells. Inhibition constant (Ki) values of compounds 13-16, 18, 19, 21-24, 27, and 28 for CB2 were >10,000, 2.8, 5.0, 2.4, 22, 0.8, 1.4, >10,000, 486, 58, 620, and 2400 nM, respectively, and those for CB1 were >10,000 nM. Preliminary in vitro results suggest that six of these compounds may be useful for therapy of neuropathic pain, neuroinflammatory diseases and immune disorders. In addition, compound 19, with its subnanomolar Ki value, could be radiolabeled with 18F and explored for PET imaging of CB2 expression.
Nucleophilic substitution of nitro groups by [18F]fluoride in methoxy-substituted ortho-nitrobenzaldehydes-A systematic study
Shen, Bin,L?ffler, Dirk,Reischl, Gerald,Machulla, Hans-Jürgen,Zeller, Klaus-Peter
experimental part, p. 216 - 224 (2009/07/25)
As model reactions for the introduction of [18F]fluorine into aromatic amino acids, the replacement of NO2 by [18F]fluoride ion in mono- to tetra-methoxy-substituted ortho-nitrobenzaldehydes was systematically investigated. Unexpectedly, the highly methoxylated precursors 2,3,4-trimethoxy-6-nitrobenzaldehyde and 2,3,4,5-tetramethoxy-6-nitrobenzaldehyde showed high maximum radiochemical yields (82% and 48% respectively). When the electrophilicity of the leaving group substituted carbon atom is expressed by its 13C NMR chemical shift a good correlation with the reaction rate at the beginning of the reaction (first min) was found (R2 = 0.89), whereas the maximum radiochemical yields correlated much poorer with this electrophilicity parameter. This may be caused by side reactions becoming influencial in the further reaction course. As possible side reactions the demethylation of methoxy groups and intramolecular redox reactions could be detected by HPLC/MS.
Studies of new indole alkaloid coupling methods for the synthesis of haplophytine
Rege, Pankaj D.,Tian, Yuan,Corey
, p. 3117 - 3120 (2007/10/03)
The two novel bisindole alkaloid structures shown can be synthesized in a few steps from the canthiphytine derivative 9.
Synthesis of the Kopsia alkaloids (+/-)-pauciflorine B, (+/-)-lahadinine B, (+/-)-kopsidasine, (+/-)-kopsidasine-N-oxide, (+/-)-kopsijasminilam and (+/-)-11-methoxykopsilongine
Magnus, Philip,Gazzard, Lewis,Hobson, Lindsay,Payne, Andrew H.,Rainey, Trevor J.,Westlund, Neil,Lynch, Vince
, p. 3423 - 3444 (2007/10/03)
Pictet-Spengler condensation of 13 with tryptamine gave 14, which was converted into 17. Treatment of 17 with phenyl chloroformate resulted in 18, which underwent transannular cyclization to,give 19. The more stable cyano-analog 22 was made by treating 18 with Tf2O/DMAP to geenrate 18f, and quenching the reaction with trimethylsilyl cyanide. Treatment of 22 with acryloyl chloride (excess) at 75 deg C gave 23, which was directly treated with N-hydroxy-2-thiopyridone/Et3N to give 24. Irradiation of 24 in the presence of r-BuSH resulted in reductive decarboxylation to give 26 and a small amount o fthe 2-thiopyridyl ether 25. Protection of the aniline nitrogen in 26 required the use of triphosgene/pyridine followed by methanol. The final step for the conversion of 27 into 28 required conjugate reduction of the α,β-unsaturated ester followed by α-hydroxylation and gave 28 (11,12-demethoxy lahadinine B). Exposure of 26 to Phl(OAc)2/MeOH cleanly gave 26a, which was directly reduced with Zn/AcOH to 29. Conversion of 29 into 30 proceeded as before, and when 30 was treated with AgBF4/THF followed by aqueous NaHCO3 it was converted into (+/-)-kopsidasine 2, completely chracterized as its derived N-oxide 2a. Treatment of 26 with AgBF4/THF followed by aqueous NaHCO3, gave 31. Oxidation of 31 with m-chloroperoxybenzoic acid resulted in the N-oxdide 32 which underwent fragmentation to give 33 when exposed to trifluoroacetic anhydrde. when the diene 33 was treated with Mn(dpm), (cat)/PhSiH3/O2 in isopropyl alcohol at 0 deg C, it was converted into kopsijasminilam 4. Peracetic acid in ErOAc (10 percent) was used to quench the AgBH4/THF conversion of 28 into 37, and resulted in 42/42a (4:1, 65 percent) along with small amounts of 38 and 41c. Application of these procedures, with some modifications, to the 11,12-dimethoxy substituted system gave (+/-)-lahadinine B 64. Treatment of 64 with triethylsilane in the presence of trifluoroacetic acid cleanly converted it into 11-methoxykopsilongine 65 (93 percent). Treatment of (+/-)-lahadinine B 64 with AgBF4/THF followed by work-up with EtOAc/MeCO3H (10 percent) gave (+/-)-pauciflorine 6 and the double bond isomer 6a.
Synthesis of (±)-lahadinine B and (±)-11-methoxykopsilongine
Magnus,Westlund
, p. 9369 - 9372 (2007/10/03)
6,7-Dimethoxytryptamine 11 was converted into the homoannular diene 19 which underwent a Diels-Alder reaction with acryloyl chloride to give 20. Subsequent radical decarboxylation in the presence of (PhSe)2 provided 22, which was converted into (±)-lahadinine B 1 and (±)-11-methoxykopsilongine 2, thus confirming their structures. (C) 2000 Elsevier Science Ltd.
