- Amino acid conjugates of aminothiazole and aminopyridine as potential anticancer agents: Synthesis, molecular docking and in vitro evaluation
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Purpose: The development of resistance to available anticancer drugs is increasingly becoming a major challenge and new chemical entities could be unveiled to compensate this therapeutic failure. The current study demonstrated the synthesis of 2-aminothiazole [S3 (a-d) and S5(a-d)] and 2-aminopyridine [S4(a-d) and S6(a-d)] derivatives that can target multiple cellular networks implicated in cancer development. Methods: Biological assays were performed to investigate the antioxidant and anticancer potential of synthesized compounds. Redox imbalance and oxidative stress are hallmarks of cancer, therefore, synthesized compounds were preliminarily screened for their antioxidant activity using DPPH assay, and further five derivatives S3b, S3c, S4c, S5b, and S6c, with significant antioxidant potential, were selected for investigation of in vitro anticancer potential. The cytotoxic activities were evaluated against the parent (A2780) and cisplatin-resistant (A2780CISR) ovarian cancer cell lines. Further, Molecular docking studies of active compounds were performed to determine binding affinities. Results: Results revealed that S3c, S5b, and S6c displayed promising inhibition in cisplatin-resistant cell lines in comparison to parent cells in terms of both resistance factor (RF) and IC50 values. Moreover, S3c proved to be most active compound in both parent and resistant cell lines with IC50 values 15.57 μM and 11.52 μM respectively. Our docking studies demonstrated that compounds S3c, S5b, and S6c exhibited significant binding affinity with multiple protein targets of the signaling cascade. Conclusion: Anticancer activities of compounds S3c, S5b, and S6c in cisplatin-resistant cell lines suggested that these ligands may contribute as lead compounds for the development of new anticancer drugs.
- Ali, Tahir,Imran, Muhammad,Li, Jing Bo,Li, Shupeng,Nadeem, Humaira,Naz, Shagufta,Sarwar, Sadia,Shah, Fawad Ali,Tan, Zhen
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p. 1459 - 1476
(2021/04/19)
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- NOVEL TRF1 MODULATORS AND ANALOGUES THEREOF
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Novel TRF1 modulators and analogues thereof. There is provided compounds of Formula I, wherein R, R1, R2 and X have meanings written in the description. Such compounds are useful as TRF1 inhibitors and, for that reason, as medicaments, in the treatment of cancer, particularly high cancer stem cell cancer like glioblastoma and lung cancer, and can be also useful for the development of additional TRF1 inhibitors and increasing knowledge about TRF1 activity.
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Paragraph 0047; 0064-0065; 0156-0157
(2020/03/26)
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- AMINO ACID DERIVATIVES FOR THE TREATMENT OF INFLAMMATORY DISEASES
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The present disclosure provides certain amino acid derivatives that inhibit NF-kB activation and are therefore useful for the treatment of inflammatory diseases. Also provided are pharmaceutical compositions containing such compounds and processes for preparing such compounds.
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Page/Page column 46
(2020/08/13)
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- A Novel Class of 7-Membered Heterocyclic Compounds
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The work presented herein describes the synthesis of a formerly inaccessible class of heterocyclic compounds. The reaction relies on α-phthalimido-amides, which are readily prepared from amino acids in 2 simple reactions steps. Under amide activation conditions in which classical keteniminium ions are not formed, the nitrile solvent is incorporated into the new fused 7-membered ring system. Due to the absence of a keteniminium intermediate, the stereogenic information in the α-position is fully retained.
- Bauer, Adriano,Borsos, Eszter,Maulide, Nuno
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supporting information
p. 3971 - 3974
(2020/05/25)
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- Kinetic investigation of the cyclopropanation process of fullerene C60 by halogenmethyl ketones under the conditions of the Bingel reaction
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The kinetics of the Bingel reaction with halogenmethyl ketones and C60 fullerene has been studied in streaming mode by sampling the reaction mixture at different time intervals and separating the components using HPLC. A quantum-chemical simulation of this cyclopropanation process has been carried out with the DFT method. The activation parameters of the cycloaddition process were determined theoretically and experimentally and correlated with each other. It has been revealed that the use of chloromethyl ketone as the cyclopropanation agent is preferable to its brominated analogue, and a two-fold excess of the substrate with respect to fullerene is the best option for the selective synthesis of mono-adducts.
- Biglova, Yulya N.,Garifullin, Rustem N.,Mustafin, Akhat G.,Sakhautdinov, Ilshat M.,Sakhautdinova, Gulnaz F.
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p. 7277 - 7285
(2020/06/18)
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- Flupirtine and retigabine as templates for ligand-based drug design of KV7.2/3 activators
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Drug induced liver injury (DILI) and tissue discoloration led to the recent discontinuation of the therapeutic use of the closely related drugs flupirtine and retigabine, respectively. Experience gained with these drugs strongly suggests that heterotetramer, voltage-gated potassium channels 2 and 3 (KV7.2/3) are valid targets for effective treatment of pain and epilepsy. Because the adverse effects are not related to the mechanism of action, it appears promising to investigate chemical modifications of these clinically validated, drug-like leads. In the present retro-metabolic drug design study, a series of 43 compounds were synthesized and characterized with regard to KV7.2/3 opening activity and efficacy. The most active compound 22d displays excellent potency (EC50 = 4 nM) and efficacy (154%) as a KV7.2/3 opener. Limited aqueous solubility hampered toxicity testing at concentrations higher than 63 μM, but this concentration was nontoxic to two hepatocellular cell lines (HEP-G2 and TAMH) in culture. The slightly less active but more soluble compound 25b (EC50 = 11 nM, efficacy 111%) showed an improved toxicity/activity ratio compared to flupirtine by three orders of magnitude and represents an attractive lead structure for the development of safer analgesics and antiepileptics.
- Surur, Abdrrahman S.,Bock, Christian,Beirow, Kristin,Wurm, Konrad,Schulig, Lukas,Kindermann, Markus K.,Siegmund, Werner,Bednarski, Patrick J.,Link, Andreas
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supporting information
p. 4512 - 4522
(2019/05/17)
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- Oximino naphthoquinone compound and preparation and application methods thereof
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The invention belongs to the technical field of medicinal compounds and medicines and relates to an oximino naphthoquinone compound and preparation and application methods thereof, particularly to a compound shown as formula (I). The oximino naphthoquinone compound can serve as a double-target selective inhibitor of STAT3 (signal transducer and activator of transcription-3) and IDO1 (indoleamine 2, 3-dioxygenase 1) for treating ovarian cancer, colon cancer, lung cancer and the like.
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Paragraph 0272; 0273
(2019/04/04)
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- Chiral sensors for determining the absolute configurations of α-amino acid derivatives
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A simple strategy for configurational assignments of alpha-amino acids has been developed by comparison of the proton NMR chemical shift values of the alpha hydrogens of N-phthaloyl protected alpha-amino acids in the presence of (R)-CSA 1 and (S)-CSA 1, respectively. Highly resolved NMR spectra can be obtained directly on the mixed solution of the chiral solvating agents with N-phthaloyl protected alpha-amino acids in NMR tubes, giving well distinguishable proton signals without interference which dramatically improve the accuracy of assignment and hasten the assigning procedure. The strategy is widely applicable for varied natural and non-natural amino acids.
- Chen, Zhongxiang,Fan, Hongjun,Yang, Shiwei,Bian, Guangling,Song, Ling
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p. 6933 - 6939
(2018/10/02)
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- Directing Group Participated Benzylic C(sp3)-H/C(sp2)-H Cross-Dehydrogenative Coupling (CDC): Synthesis of Azapolycycles
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An efficient method to construct azapolycycles via directing group participated benzylic C(sp3)-H/C(sp2)-H cross-dehydrogenative coupling reactions is described. The reaction proceeded through a palladium catalyzed C(sp3)-H activation followed by coupling with a C(sp2)-H bond of quinoline to afford the azapolycyclic compounds. The reaction works with a broad substrate scope affording the products in moderate to good yields with excellent diastereoselectivities. Control experiments further supported the proposed mechanism.
- Jiang, Yaojia,Deng, Gongtao,Zhang, Shuaishuai,Loh, Teck-Peng
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supporting information
p. 652 - 655
(2018/02/09)
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- Synthesis and study of modified polyvinyl alcohol containing amino acid moieties as anticancer agent
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A series of new phthalimides compounds[3-7]a-i were synthesized from reaction of Malic anhydride, phthalic anhydride, nitro phthalic anhydride, 2-phenyl-4H-benzo[d][1,3]oxazin-4-one, 2-(4-nitrophenyl)-4H-benzo[d][1,3]oxazin-4-one with different amino acids as glycine, alanine, valine, leucine, isoleucine, serine, threonine, tyrosine and Phenyl alanine [1]a-i under fusion conditions. Compounds [3-7]a-i react with SOCl2 in the presence of benzene to produce compounds [8-12]a-i. Chemical modification of Poly(vinyl alcohol)were obtained by reaction of PVA with compounds [8-12]a-i using the dimethyl formamide to give compounds [13-17]a-i. The structure of the synthesized compounds was characterized by their analytical and spectral data as, IR spectra, 1H, 13C-NMR, Elemental analysis (CHN), UV-Vis Spectroscopy, Scanning electron microscopy (SEM), Antibacterial activity were screened via two kinds of bacteria. Also, anticancer activity were examined for most of the modified polyvinyl alcohol.
- Samir, Ali H.,Saeed, Ruwaidah S.,Matty, Fadhel S.
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p. 286 - 294
(2018/03/21)
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- Bioinspired Deamination of α-Amino Acid Derivatives Catalyzed by a Palladium/Nickel Complex
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An efficient bioinspired deamination method of both natural and unnatural amino acid derivatives has been developed. This method provides easy access to a wide variety of useful α, β-unsaturated carbonyl compounds. The reaction is realized with two transition metal catalysts (palladium and Nickel) in-easy handling procedure. A possible reaction pathway is also proposed and the control experiments support the involvement of the palladium-catalyzed inert sp3 C?H activation as one of the key steps. (Figure presented.).
- Deng, Gongtao,Chen, Jie,Sun, Wangbin,Bian, Kehan,Jiang, Yaojia,Loh, Teck-Peng
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supporting information
p. 3900 - 3905
(2018/09/12)
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- Synthesis of Quaternary α-Fluorinated α-Amino Acid Derivatives via Coordinating Cu(II) Catalytic α-C(sp3)-H Direct Fluorination
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A coordinating, copper-catalyzed direct α-C(sp3)-H fluorination method has been developed to prepare vital quaternary α-fluorinated α-amino acid derivatives. A Cu(II) catalytic SET oxidative addition mechanism is proposed, involving a key fluoride-coupled Cu(II) charge transfer complex. The protocol can tolerate a rich variety of α-amino acids, for which the auxiliary group is removed in high yield and substituted for the direct preparation of dipeptide derivatives with detachable, single absolute configurations of the target compounds.
- Wei, Qiang,Ma, Yao,Li, Li,Liu, Qingfei,Liu, Zijie,Liu, Gang
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supporting information
p. 7100 - 7103
(2018/11/24)
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- Discovery of dehydroabietic acid sulfonamide based derivatives as selective matrix metalloproteinases inactivators that inhibit cell migration and proliferation
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A series of dehydroabietic acid (DHAA) dipeptide derivatives containing the sulfonamide moiety were designed, synthesized and evaluated for inhibition of MMPs as well as the effects of in vitro cell migration. These compounds exhibited relatively good inhibition activity against MMPs with IC50 values in low micromolar range. A docking study of the most active compound 8k revealed key interactions between 8k and MMP-3 in which the sulfonamide moiety and the dipeptide group were important for improving activity. It is noteworthy that further antitumor activity screening revealed that some compounds exhibited better inhibitory activity than the commercial anticancer drug 5-FU. In particular, compound 8k appeared to be the most potent compound against the HepG2 cell line, at least partly, by inhibition of the activity of MMP-3 and apoptosis induction. The treatment of HepG2 cells with compound 8k resulted in inhibition of in vitro cell migration through wound healing assay and G1 phase of cell cycle arrested. In addition, 8k-induced apoptosis was significantly facilitated in HepG2 cells. Thus, we conclude that DHAA dipeptide derivatives containing the sulfonamide moiety may be the potential MMPs inhibitors with the ability to suppress cells migration.
- Huang, Ri-Zhen,Liang, Gui-Bin,Huang, Xiao-Chao,Zhang, Bin,Zhou, Mei-Mei,Liao, Zhi-Xin,Wang, Heng-Shan
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p. 979 - 992
(2017/08/01)
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- Cooperative Effects between Chiral Cpx–Iridium(III) Catalysts and Chiral Carboxylic Acids in Enantioselective C?H Amidations of Phosphine Oxides
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An enantioselective C?H amidation of phosphine oxides by using an iridium(III) catalyst bearing an atropchiral cyclopentadienyl (Cpx) ligand is reported. A very strong cooperative effect between the chiral Cpx ligand and a phthaloyl tert-leucine enabled the transformation. Matched–mismatched cases of the different acid enantiomers are shown. The amidated P-chiral arylphosphine oxides are formed in yields of up to 95 % and with excellent enantioselectivities of up to 99:1 er. Enantiospecific reduction provides access to valuable P-chiral phosphorus(III) compounds.
- Jang, Yun-Suk,Dieckmann, Michael,Cramer, Nicolai
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supporting information
p. 15088 - 15092
(2017/10/11)
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- 1-Imidoalkylphosphonium salts with modulated Cα–P+ bond strength: synthesis and application as new active α-imidoalkylating agents
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An effective synthesis of the hitherto unknown 1-imidoalkylphosphonium salts has been developed in the reported study. The crucial step in the method included the decarboxylative α-methoxylation of N-phthaloyl- or N-succinylamino acids to the corresponding N-(1-methoxyalkyl)imides, followed by the displacement of the methoxy group by the triarylphosphonium group through melting of the imide derivative with triarylphosphonium tetrafluoroborate. The imidoalkylating properties of the obtained 1-imidoalkylphosphonium salts were tested using the Tscherniac–Einhorn-type reaction with aromatic hydrocarbons as a model reaction. It was found that the Cα–P+ bond strength can be considerably reduced and the imidoalkylation of arenes can be markedly facilitated using 1-imidoalkylphosphonium salts derived from triarylphosphines with electron-withdrawing substituents such as tris(m-chorophenyl)phosphine, tris(p-chlorophenyl)phosphine and tris[p-(trifluoromethyl)phenyl]phosphine. Microwave irradiation also considerably facilitates the cleavage of the highly polar Cα–P+ bond.
- Adamek, Jakub,Mazurkiewicz, Roman,W?grzyk, Anna,Erfurt, Karol
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supporting information
p. 1446 - 1455
(2017/08/02)
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- Design, synthesis and anti-cancer activity evaluation of podophyllotoxin-norcantharidin hybrid drugs
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In this study, we designed and synthesized eighteen podophyllotoxin-norcantharidin hybrid drugs which could exhibit more potent anti-cancer activity than the parent drugs. Through the anti-proliferation assay, the most potent anti-cancer agent was screened out, namely Q9 (IC50?=?0.88?±?0.18?μM against MCF-7 cell line), and it showed lower cytotoxicity against non-cancer cells, human embryonic kidney cells (293T) (IC50?=?54.38?±?3.78?μM). Additionally, based on the flow cytometry analysis result, it can cause a remarkable cell cycle arrest at G2/M phase and induce apoptosis in MCF-7 cells more significantly than podophyllotoxin or norcantharidin per se. Moreover, the expression of cell cycle relative protein CDK1 was up regulated while a protein required for mitotic initiation, Cyclin B1 was down regulated. Furthermore, according to the confocal microscopy observation results, it was shown that Q9 was a potent tubulin polymerization inhibitor and the effect is comparable to that of colchicine. For further investigation on the aforementioned mechanisms, we performed western blot experiments, thus finding the increase of the cleavage of PARP. Consistent with these new findings, molecular docking observations suggested that compound Q9 could be developed as a potential anticancer agent.
- Han, Hong-Wei,Qiu, Han-Yue,Hu, Cui,Sun, Wen-Xue,Yang, Rong-Wu,Qi, Jin-Liang,Wang, Xiao-Ming,Lu, Gui-Hua,Yang, Yong-Hua
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supporting information
p. 3237 - 3242
(2016/07/12)
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- Halofluorination of N-protected α,β-dehydro-α-amino acid esters—A convenient synthesis of α-fluoro-α-amino acid derivatives
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N-protected dehydroamino acid methyl esters have been converted to α-fluoro-β-halo amino acid derivatives under halofluorination reaction conditions. The influences of the nitrogen protecting group of the substrates and of the halonium electrophile on the reaction outcome and the stability of the obtained products have been studied. Furthermore, reduction of the halogen substituent (Cl or Br) under radical conditions provided a possibility for follow-up reactions. Nucleophilic substitution reactions, however, failed.
- Ulbrich, Dirk,Daniliuc, Constantin G.,Haufe, Günter
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supporting information
p. 65 - 75
(2016/07/11)
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- Phthiobuzonum derivative and its preparation and use
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The invention relates to a ftibamzone derivative and a preparation method and an application thereof, and belongs to the technical field of ftibamzone medicament synthesis. Pharmacological experiments prove that the ftibamzone derivative of the invention has obvious cytotoxic activity and antiviral activity, and can be used for treating viral diseases such as tumor, herpes, trachoma, and the like.
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Paragraph 0118; 0120
(2016/11/09)
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- Decarboxylative fluorination of aliphatic carboxylic acids via photoredox catalysis
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The direct conversion of aliphatic carboxylic acids to the corresponding alkyl fluorides has been achieved via visible light-promoted photoredox catalysis. This operationally simple, redox-neutral fluorination method is amenable to a wide variety of carboxylic acids. Photon-induced oxidation of carboxylates leads to the formation of carboxyl radicals, which upon rapid CO2-extrusion and F? transfer from a fluorinating reagent yield the desired fluoroalkanes with high efficiency. Experimental evidence indicates that an oxidative quenching pathway is operable in this broadly applicable fluorination protocol.
- Ventre, Sandrine,Petronijevic, Filip R.,Macmillan, David W. C.
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supporting information
p. 5654 - 5657
(2015/05/20)
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- Stereoselective synthesis of chiral α-amino-β-lactams through palladium(II)-catalyzed sequential monoarylation/amidation of C(sp 3)-H Bonds
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Give Me an Ar, give Me an N! Arylation of the methyl group in a simple derivative of readily available alanine under palladium catalysis was followed by intramolecular amidation at the same position to give chiral α-amino-β-lactams with a wide range of aryl substituents (see scheme; Phth=phthaloyl). The α-amino-β-lactams were obtained in moderate to high yields with good functional-group tolerance and high diastereoselectivity. Copyright
- Zhang, Qi,Chen, Kai,Rao, Weihao,Zhang, Yuejun,Chen, Fa-Jie,Shi, Bing-Feng
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supporting information
p. 13588 - 13592
(2014/01/06)
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- New fluorescent and colorimetric chemosensors based on the rhodamine detection of Hg2+ and Al3+ and application of imaging in living cells
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Employing the "OffeOn" switching of the spirocyclic moiety in Rhodamine B derivatives, three sensors were designed and characterized as new fluorescent probes for detecting Hg2+ and Al3+ in the environment, respectively. The first probe exhibited chromogenic and fluorogenic selectivity to detection of Hg2+ in methanol-H2O (4:6, v/v, HEPES, pH 7.0). The first and second probes displayed fluorescence intensity enhancement following Hg2+ coordination with limits of detection for Hg2+ at the ppb level. The limit of detection based on 3 blank/k was calculated to be 2.5 × 10-8 M and 4.2 × 10-8 M, respectively. The third probe contained a benzyl group which resulted in better selectivity for Al3+. Job's plot clearly suggested the formation of 1:1 complexation behavior between the three probes and Hg 2+ or Al3+. The three probes can be used as a fluorescent probe for monitoring Hg2+ or Al3+ in living cells with satisfying results, which demonstrates the value of the probes in practical applications in environmental and biological systems.
- Yan, Fanyong,Wang, Meng,Cao, Donglei,Yang, Ning,Fu, Yang,Chen, Li,Chen, Ligong
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- Hydrogen bonding chains and rings structural motifs in new series of N-phthaloyl aminocarboxylic acid derivatives. Solid state microwave synthesis, structural chemistry, computational calculations and antimicrobial activity
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A series of six N-phthaloyl aminocarboxylic acids were synthesized by using improved microwave irradiation with a multimode reactor. X-ray single crystal diffraction established the molecular structure of three N-protected aminocarboxylic acids derivatives, and spectral data agree with these in solution. The hydrogen bonding characteristics of this class of molecules are discussed on the basis of crystal structural analyses, MP2/DFT quantum calculations and Hirshfeld surfaces analyses. The relative strengths of the structural O-H?O and C-H?O hydrogen bonding chain and ring motifs are compared. Antimicrobial activities of 2-(1,3-dioxoisoindolin-2-yl)propanoic acid, 2-(1,3-dioxoisoindolin-2-yl)-3-phenylpropanoic acid and 2-(4-(1,3-dioxoisoindolin-2-yl)phenyl)acetic acid, were screened against three pathogenic strains; only the first two compounds were found to be quite sensitive against Gram +ve and Gram -ve bacterial strains, respectively. A relative structure-function relationship is observed.
- Al-Farhan, Khalid,Ghazzali, Mohamed,Al-Hazimi, Hassan M.A.,El-Faham, Ayman,Reedijk, Jan
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scheme or table
p. 269 - 275
(2011/08/03)
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- Synthesis and antiviral activity of novel 1,3,4-thiadiazine derivatives
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A series of novel 1,3,4-thiadiazine derivatives were synthesized via chemical optimization on phthiobuzone. Their anti-herpes simplex virus (HSV) activities in vitro were also tested. Several compounds exhibited more highly potent anti-HSV activity and much higher selectivity index (SI) values than those of phthiobuzone. The most potent anti-HSV compound was 4f, which showed marked inhibition against HSV-1 (IC50=77.04μg/ml) and HSV-2 (IC50=30.00μg/ml). Meanwhile it had low cytotoxicity (CC 50=1000.00μg/ml), resulting in high (SIHSV-1= 12.98, SIHSV-2=33.33, respectively). Furthermore, a computational study for prediction of absorption, distribution, metabolism, excretion (ADME) properties of compound 4f was performed by determination of topological polar surface area, absorption and Lipinski parameters.
- Yang, Yajun,Feng, Ziming,Jiang, Jianshuang,Yang, Yanan,Pan, Xiandao,Zhang, Peicheng
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scheme or table
p. 1016 - 1019
(2011/10/08)
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- Catalytic asymmetric protonation of α-amino acid-derived ketene disilyl acetals using P -Spiro diaminodioxaphosphonium barfates as chiral proton
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Chiral diaminodioxaphosphonium salts have been developed and their unique abilities as a chiral proton have been revealed through the establishment of a highly enantioselective protonation of α-amino acid-derived ketene disilyl acetals.
- Uraguchi, Daisuke,Kinoshita, Natsuko,Ooi, Takashi
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supporting information; experimental part
p. 12240 - 12242
(2010/11/19)
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- Cyclomaltooligosaccharide-assisted spectroscopic discrimination of phthalimido-derived amino acids through the formation of molecular aggregates
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Spectroscopic evidence was used to demonstrate the formation of molecular associates in an aqueous solution of phthalimido tryptophan. These molecular associates are loosely formed through π-π aromatic stacking, properties that are not sufficient to cause NMR spectroscopic enantiomeric discrimination. A cyclomaltooligosaccharide with a larger cavity, such as cyclomaltooctaose (γ-cyclodextrin), is capable of forming a ternary complex with these molecular associates and enhances π-π aromatic stacking interactions, resulting in NMR enantiomeric discrimination. Electrospray-ionization mass spectroscopy (ESIMS) and NOESY two-dimensional NMR spectroscopic methods were used to study these complexes. Association constants and thermodynamic data for these cyclomaltooligosaccharide complexes were also estimated.
- Jursic, Branko S.,Patel, Paresh K.
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p. 2858 - 2866
(2007/10/03)
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- Structure-driven design and synthesis of chiral dioxocyclam derivatives
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Based on an analysis of previously reported structures and a potential geometry fit with substrates, a new family of chiral dioxocyclam derivatives have been designed. The synthesis of those ligands was accomplished starting from l-proline and α-d-amino acids (converted to β-amino acids) with a key step of macrocyclization reaction of amino esters. All ligands were converted into neutral copper(II) complexes (amide groups underwent deprotonation of upon treatment of ligands with copper(II) acetate). The complexes exhibit the desired shape of their active surfaces, as proved by X-ray analysis.
- Achmatowicz, Micha?,Szumna, Agnieszka,Zieliński, Tomasz,Jurczak, Janusz
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p. 9031 - 9041
(2007/10/03)
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- The synthesis of N-acyl-2-hydroxymethyl aziridines of biological interest
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A practical synthesis of the title compounds from protected amino acylazides is described. All the compounds might be considered as a novel class of dipeptide isostere precursors; they all induce lymphocyte proliferation and protein production as observed from preliminary biological tests.
- Medjahed,Tabet Zatla,Kajima Mulengi,Baba Ahmed,Merzouk
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p. 1211 - 1213
(2007/10/03)
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- Microwave-assisted rapid synthesis of phthalimide derivatives
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A simple, extremely fast, and high yielding method for the reaction of phthalic anhydride with a number of amino acids using microwave irradiation under solventless 'dry' conditions has been developed. The phthalimide derivatives are prepared in excellent yields and without racemization.
- Hajipour,Mallakpour,Imanzadeh
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p. 250 - 251
(2007/10/03)
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- Imides
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Cyclic imides are inhibitors of tumor necrosis factor α and can be used to combat cachexia, endotoxic shock, and retrovirus replication. A typical embodiment is 2-(2,6-dioxo-3-piperidinyl)-4-azaisoindoline-1,3-dione.
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- Cyclic amides
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Cyclic amides are inhibitors of tumor necrosis factor and can be used to combat cachexia, endotoxic shock, and retrovirus replication. A typical embodiment is 3-phenyl-3-(1-oxoisoindolin-2-yl)propionamide.
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- Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 7. Cyclisation of amino acid derived α-phthalimidoacyl ylides to give pyrroloisoindolediones
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A series of 11 amino acid-derived stabilised ylides 12-14 and 16 have been prepared and characterised. In one case, for compound 17, an X-ray structure determination supports formulation of the compounds as phosphonium enolates. Flash vacuum pyrolysis (FVP) of 12 and 13 at 500°C results in loss of R23PO between the ylide function and one carbonyl of the phthalimido group to give products characterised spectroscopically as the pyrroloisoindolediones 18. The identity of these is also supported by the results of 13C and 15N labelling experiments, but owing to their high reactivity complete separation from the phosphine oxide was not generally possible even when Bu3PO rather than Ph3PO was involved. Chromatographic purification of 29, similarly produced by FVP of 14, led to partial hydrolysis, rearrangement and decarboxylation to give 30. FVP of 12 at 750°C gave the 1-unsubstituted pyrroloisoindolediones 19 in two cases.
- Aitken, R. Alan,Cooper, Harris R.,Mehrotra, Amit P.
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p. 475 - 483
(2007/10/03)
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- Ring closure of N-phthaloylglutamines
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Cyclic imides are inhibitors of tumor necrosis factor α and can be used to combat cachexia, endotoxic shock, and retrovirus replication. A typical embodiment is 2-(2,6-dioxo-3-piperidinyl)-4-azaisoindoline-1,3-dione.
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- SULFUR YLIDES. 3. SYNTHESIS OF KETO-GROUP STABILIZED AMINO-CONTAINING SULFUR YLIDES FROM AMINO ACIDS
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An effective path of synthesis was developed of new synthetic intermediates, the optically active, keto-group stabilized amino-substituted sulfur ylides.
- Tolstikov, G. A.,Galin, F. Z.,Lakeev, S. N.,Khalilov, L. M.,Sultanova, V. S.
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p. 535 - 541
(2007/10/02)
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- Intramolecular Friedel-Crafts Acylation of N-Phthaloyl-Substituted Arylalanyl and Homophenylalanyl Chlorides
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N-Phthaloyl-protected arylalanyl and homophenylalanyl chlorides 5 are acylated intramolecularly to 2-phthalimido-1-indanones 6 and -1-tetralone (6d) with AlCl3 (two-fold molar amounts) or catalytic amounts of FeCl3.The cycloacylation to the tetralone 6d with AlCl3 or FeCl3 proceeds without racemisation in very good yields, whereas the cycloacylation to the indanone 6a with FeCl3 gives rise to racemisation.Mixed anhydrides 11 of N-phthaloyl-α-amino acids and trifluoromethanesulfonate were prepared from the N-phthaloylamino acid chlorides and silver triflate.Acylation of arenes 12 with 11a as well as cycloaddition of (S)-O-methyl-N-phthaloyltyrosine triflate can be achieved without racemisation and without a catalyst.
- Effenberger, Franz,Steegmueller, Dieter,Null, Volker,Ziegler, Thomas
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p. 125 - 130
(2007/10/02)
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