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Pleuromutilin derivative with 1, 3, 4-oxadiazole side chain and preparation and application thereof
The invention belongs to the field of medicinal chemistry, and particularly relates to a pleuromutilin derivative with a 1, 3, 4-oxadiazole side chain and preparation and application thereof The pleuromutilin derivative with the 1, 3, 4-oxadiazole side chain is a compound shown in a formula 2 or a pharmaceutically acceptable salt thereof, and a solvent compound, an enantiomer, a diastereoisomer and a tautomer of the compound shown in the formula 2 or the pharmaceutically acceptable salt thereof or a mixture of the solvent compound, the enantiomer, the diastereoisomer and the tautomer in any proportion, including a racemic mixture. The pleuromutilin derivative has good antibacterial activity, is especially suitable for being used as a novel antibacterial agent for systemic system infection of animals or human beings, and has good water solubility.
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Paragraph 0055-0056; 0070; 0090; 0092; 0095; 0103

(2021/07/24)

The discovery of novel small molecule allosteric activators of aldehyde dehydrogenase 2
Aldehyde dehydrogenase 2 (ALDH2) plays important role in ethanol metabolism, and also serves as an important shield from the damage occurring under oxidative stress. A special inactive variant was found carried by 35–45% of East Asians. The variant carriers have recently been found at the higher risk for the diseases related to the damage occurring under oxidative stress, such as cardiovascular and cerebrovascular diseases. As a result, ALDH2 activators may potentially serve as a new class of therapeutics. Herein, N-benzylanilines were found as novel allosteric activators of ALDH2 by computational virtual screening using ligand-based and structure-based screening parallel screening strategy. Then a structural optimization was performed and has led to the discovery of the compound C6. It has good activity in vitro and in vivo, which could reduce infarct size by ～70% in ischemic stroke rat models. This study provided good lead compounds for the further development of ALDH2 activators.
Tian, Wei,Guo, Jiapeng,Zhang, Qingsen,Fang, Shaoyu,Zhou, Ruolan,Hu, Jian,Wang, Mingping,Zhang, Yuefan,Guo, Jin-Min,Chen, Zhuo,Zhu, Ju,Zheng, Canhui
(2020/12/30)

Half-Sandwich Ruthenium Complexes of Amide-Phosphine Based Ligands: H-Bonding Cavity Assisted Binding and Reduction of Nitro-substrates
We present synthesis and characterization of two half-sandwich Ru(II) complexes supported with amide-phosphine based ligands. These complexes presented a pyridine-2,6-dicarboxamide based pincer cavity, decorated with hydrogen bonds, that participated in the binding of nitro-substrates closer to the Ru(II) centers, which is further supported with binding and docking studies. These ruthenium complexes functioned as the noteworthy catalysts for the borohydride mediated reduction of assorted nitro-substrates. Mechanistic studies not only confirmed the intermediacy of [Ru-H] in the reduction but also asserted the involvement of several organic intermediates during the course of the catalysis. A similar Ru(II) complex that lacked pyridine-2,6-dicarboxamide based pincer cavity substantiated its unique role both in the substrate binding and the subsequent catalysis.
Pachisia, Sanya,Kishan, Ram,Yadav, Samanta,Gupta, Rajeev
p. 2009 - 2022
(2021/02/06)

Production process of ethyl m-aminobenzoate
The invention provides a production process of ethyl m-aminobenzoate, and the production process comprises the following steps: filling a trickle bed reactor with a catalyst DCyPP.Pd(OAc)2 and potassium carbonate, adding a mixture of 3-chloroaniline and ethanol, introducing carbon monoxide, keeping the pressure in the reactor at 0.1-0.2 MPa, carrying out carbonylation esterification reaction, and performing purifying by a rectifying tower to obtain the ethyl m-aminobenzoate with the molar yield of 97%, wherein the purity of the ethyl m-aminobenzoate is more than 98.5%. According to the method, ethyl m-aminobenzoate can be continuously produced, reaction raw materials are convenient and easy to obtain, the process is simple, reaction conditions are mild, reaction energy consumption is low, no waste acid is generated in the reaction process, and the method is suitable for large-scale production.
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Paragraph 0026-0045

(2021/04/21)

Synthesis and biological evaluation of 2,5-diaryl-1,3,4-oxadiazole derivatives as novel Src homology 2 domain-containing protein tyrosine phosphatase 2 (SHP2) inhibitors
The Src homology-2 domain containing-protein tyrosine phosphatase-2 (SHP2) is a convergent node for oncogenic cell-signaling cascades including the PD-L1/PD-1 pathway. As an oncoprotein as well as a potential immunomodulator, SHP2 has now emerged as an attractive target for novel anti-cancer agents. Although significant progress has been made in identifying chemotypes of SHP2 inhibitors, these specific compounds might not be clinically useful to inhibit frequently encountered mutated SHP2 variants. Consequently, it is highly desirable to develop chemically different SHP2 inhibitors sensitive to SHP2 mutants. This work developed a new type of SHP2 inhibitors with 2,5-diaryl-1,3,4-oxadiazole scaffold. The representative compound 6l exhibited SHP2 inhibitory activity with IC50 of 2.73 ± 0.20 μM, showed about 1.56-fold, 5.26-fold, and 7.36-fold selectivity for SHP2 over SHP1, PTP1B and TCPTP respectively. Further investigations confirmed that 6l behaved as mixed-type inhibitor sensitive to leukemia cell TF-1 and inhibited SHP2 mediated cell signaling and proliferation. Molecular dynamics simulation provided more detailed information on the binding modes of compounds and SHP2 protein. These preliminary results could provide a possible opportunity for the development of novel SHP2 inhibitors sensitive to SHP2 mutants with optimal potency and improved pharmacological properties.
Meng, Xiang-Dong,Gao, Li-Xin,Wang, Zhi-Jia,Feng, Bo,Zhang, Chun,Satheeshkumar, Rajendran,Li, Jia,Zhu, Yun-Long,Zhou, Yu-Bo,Wang, Wen-Long
(2021/10/04)

Biological Characterization, Mechanistic Investigation and Structure-Activity Relationships of Chemically Stable TLR2 Antagonists
Toll-like receptors (TLRs) build the first barrier in the innate immune response and therefore represent promising targets for the modulation of inflammatory processes. Recently, the pyrogallol-containing TLR2 antagonists CU-CPT22 and MMG-11 were reported; however, their 1,2,3-triphenol motif renders them highly susceptible to oxidation and excludes them from use in extended experiments under aerobic conditions. Therefore, we have developed a set of novel TLR2 antagonists (1–9) based on the systematic variation of substructures, linker elements, and the hydrogen-bonding pattern of the pyrogallol precursors by using chemically robust building blocks. The novel series of chemically stable and synthetically accessible TLR2 antagonists (1–9) was pharmacologically characterized, and the potential binding modes of the active compounds were evaluated structurally. Our results provide new insights into structure-activity relationships and allow rationalization of structural binding characteristics. Moreover, they support the hypothesis that this class of TLR ligands bind solely to TLR2 and do not directly interact with TLR1 or TLR6 of the functional heterodimer. The most active compound from this series (6), is chemically stable, nontoxic, TLR2-selective, and shows a similar activity with regard to the pyrogallol starting points, thus indicating the variability of the hydrogen bonding pattern.
Bermudez, Marcel,Grabowski, Maria,Murgueitio, Manuela S.,Rademann, J?rg,Rudolf, Thomas,Tiemann, Markus,Varga, Péter,Weindl, Günther,Wolber, Gerhard
(2020/06/08)

Improving the Potency of Cancer Immunotherapy by Dual Targeting of IDO1 and DNA
Herein we report the first exploration of a dual-targeting drug design strategy to improve the efficacy of small-molecule cancer immunotherapy. New hybrids of indoleamine 2,3-dioxygenase 1 (IDO1) inhibitors and DNA alkylating nitrogen mustards that respectively target IDO1 and DNA were rationally designed. As the first-in-class examples of such molecules, they were found to exhibit significantly enhanced anticancer activity in vitro and in vivo with low toxicity. This proof-of-concept study has established a critical step toward the development of a novel and effective immunotherapy for the treatment of cancers.
Fang, Kun,Dong, Guoqiang,Wang, Hongyu,He, Shipeng,Wu, Shanchao,Wang, Wei,Sheng, Chunquan
supporting information
p. 30 - 36
(2017/12/26)

AMINATION AND HYDROXYLATION OF ARYLMETAL COMPOUNDS
In one aspect, the present disclosure provides methods of preparing a primary or secondary amine and hydroxylated aromatic compounds. In some embodiments, the aromatic compound may be unsubstituted, substituted, or contain one or more heteroatoms within the rings of the aromatic compound. The methods described herein may be carried out without the need for transition metal catalysts or harsh reaction conditions.
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Paragraph 0253; 0257

(2018/03/25)

Selective Optimization of Pranlukast to Farnesoid X Receptor Modulators
Selective optimization of side activities (SOSA) offers an alternative entry to early drug discovery and may provide rapid access to bioactive new chemical entities with desirable properties. SOSA aims to reverse a drug's side activities through structural modification and to design out the drug's original main action. We identified a moderate side activity for the cysteinyl leukotriene receptor 1 (CysLT1R) antagonist pranlukast on the farnesoid X receptor (FXR). Systematic structural modification of the drug allowed remarkable optimization of its partial FXR agonism to sub-nanonmolar potency. The resulting FXR modulators lack any activity on CysLT1R and are characterized by high selectivity, high metabolic stability, and low toxicity. With their favorable in vitro profile, these SOSA-derived FXR modulators constitute a new FXR ligand chemotype that appears suitable for further preclinical evaluation.
Schierle, Simone,Schmidt, Jurema,Kaiser, Astrid,Merk, Daniel
p. 2530 - 2545
(2018/11/25)

N-(5-Methyl-1,3-Thiazol-2-yl)-2-{[5-((Un)Substituted- Phenyl)1,3,4-Oxadiazol-2-yl]Sulfanyl}acetamides. Unique Biheterocycles as Promising Therapeutic Agents
An electrophile, 2-bromo-N-(5-methyl-1,3-thiazol-2-yl)acetamide, was synthesized by the reaction of 5-methyl-1,3-thiazol-2-amine and bromoacetyl bromide in an aqueous medium. In a parallel scheme, a series of (un)substituted benzoic acids was converted sequentially into respective esters, acid hydrazides, and then into 1,3,4-oxadiazole heterocyclic cores. The electrophile was coupled with the aforementioned 1,3,4-oxadiazoles to obtain the targeted bi-heterocyles. Structural analysis of the synthesized compounds was performed by IR, EI-MS, 1H NMR, and 13C NMR. The enzyme inhibition study of these molecules was carried out against four enzymes, namely, acetylcholinesterase, butyrylcholinesterase, α-glucosidase, and urease. The interactions of these compounds with respective enzymes were recognized by their in silico study. Moreover, their cytotoxicity was also determined to find out their utility as possible therapeutic agents.
Abbasi,Ramzan,Aziz-ur-Rehman,Siddiqui,Shah,Hassan,Seo,Ashraf,Mirza,Ismail
p. 801 - 811
(2019/02/27)

7-substituted-4-aryl coumarins compound, and preparation method and application thereof
The invention discloses a 7-substituted-4-aryl coumarins compound, and a preparation method and an application thereof and belongs to the technical field of antitumor drugs. The 7-substituted-4-aryl coumarins compound is acquired in the manner of modifying and remolding 4 and 7 loci of the coumarins. The structural formula is shown in the specification. A pharmacological experiment proves that such a compound has an excellent antitumor activity, can be used for preparing the antitumor drugs, is capable of supplying a new selection for the development and application of the antitumor drugs and further can be applied to the design and optimization of the antitumor drugs. The preparation method of the compound has the advantages of easily acquired raw materials, mild reaction condition, easily realized synthesis method, simple reaction process and operation, low-cost reagents and higher yield.
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Paragraph 0061; 0062

(2017/08/02)

Copper-coordination polymer-controlled Cu@N-rGO and CuO@C nanoparticle formation: Reusable green catalyst for A3-coupling and nitroarene-reduction reactions
The intriguing structural properties of coordination polymers (COPs), together with the huge variety of metal ions and organic linkers to choose from, make COPs potential precursors for fabricating carbon-encapsulated metal and metal oxide nanoparticles (NPs). Herein, we have studied the role of the COP structural assembly, prepared through making subtle changes to the ligand structure, on the formation of NPs in a carbon matrix. Cu-COPs (Cu-COP-1-Cu-COP-7), generated using different amino acid-based reduced Schiff base phenolic chelating ligands, exhibited crystalline structures with differing structural organization in the solid state. Interestingly, the calcination of Cu-COP-1 and Cu-COP-5 at 330 °C produced pure CuNPs, whereas Cu-COP-2, Cu-COP-3, Cu-COP-4 and Cu-COP-7 gave CuONPs encapsulated by carbon matrix. The calcination of Cu-COP-6 produced both CuNPs and CuONPs together in the carbon matrix. The formation of CuNPs and CuONPs in the carbon matrices was unambiguously confirmed by PXRD and XPS studies. The sizes and morphologies of the Cu/CuONPs were analyzed using HR-TEM and FE-SEM. BET studies revealed higher surface areas with small pores for the CuNPs encapsulated by carbon and lower surface areas with higher porosity for the CuONP-carbon matrix. Raman spectra revealed the formation of a nitrogen-doped reduced graphene oxide (N-rGO) carbon matrix in CuNPs-1. The N-rGO coverage and high surface area with small pores provided CuNPs-1 with good stability in strong acid (10 M H2SO4). Importantly, the fabricated N-rGO-encapsulated CuNPs-1 and carbon-covered CuONPs-4 nanocomposites were used as green catalysts in solvent-free neat A3-coupling and nitroarene-reduction reactions, respectively. The products were confirmed using 1H-NMR spectra. The recovered CuNPs-1 and CuONPs-4 catalysts, after the completion of the reactions, also showed similar catalytic activity at up to five cycles, without significant loss of catalytic activity. Thus, the present studies demonstrate the influence of Cu-COP structural assembly on the formation of Cu/CuONPs as well as the carbon matrix, and open the possibility of fabricating functional nanomaterials from the vast number of available COPs with intriguing structural motifs.
Vinod Kumar, Vadivel,Rajmohan, Rajamani,Vairaprakash, Pothiappan,Mariappan, Mariappan,Anthony, Savarimuthu Philip
p. 11704 - 11714
(2017/09/18)

Non-deprotonative primary and secondary amination of (hetero)arylmetals
Herein we disclose a novel method for the facile transfer of primary (-NH2) and secondary amino groups (-NHR) to heteroaryl-as well as arylcuprates at low temperature without the need for precious metal catalysts, ligands, excess reagents, protecting and/or Erecting groups. This one-pot transformation allows unprecedented functional group tolerance and it is wellsuited for the amination of electron-rich, electron-deficient as well as structurally complex (hetero)arylmetals. In some of the cases, only catalytic amounts of a copper (l) salt is required.
Zhou, Zhe,Ma, Zhiwei,Behnke, Nicole Erin,Gao, Hongyin,Kürti, László
supporting information
p. 115 - 118
(2017/05/16)

Pyrido[3, 4-b]indole urea compound and use thereof as IDO inhibitor
The invention discloses a pyrido[3, 4-b]indole urea compound. Specifically, the compound has substitution at the 9- position of pyrido[3, 4-b]indole, and the connection bridge is a urea structure. The invention also discloses a preparation method of the compound and use thereof as an IDO (indoleamine 2, 3-dioxygenase) inhibitor. The compound provided by the invention can be used for prevention and/or treatment of various diseases, like Alzheimer's disease, cataract, cell immune activation related infections, autoimmune diseases, AIDS, cancer, depression or tryptophan metabolic disorder, etc. (formula (I)).
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Paragraph 0072-0074

(2017/09/13)

Synthesis, spectral analysis and antibacterial evaluation of 5-substituted-1,3,4-oxadiazol-2-yl 4-(4-methylpiperidin-1-ylsulfonyl)benzyl sulfides
Owing to valuable biological activities of 1,3,4-oxadiazole, sulfamoyl and piperidine functionalities, some new 1-(4-{[(5-substituted-1,3,4-oxadiazol-2-yl) thio]methyl}benzene sulfonyl)-4-methylpiperidine (6a-o) derivatives have been introduced. The target molecules were synthesized from different aralkyl/aryl carboxylic acids, 1a-o, through a series of steps. First the compounds, 1a-o, were converted to heterocyclic 1,3,4-oxadiazole nucleophiles, 4a-o. Second an electrophile as 1-(4-bromomethylbenzenesulfonyl)-4-methylpiperidine (5) was synthesized from 4-methylpiperidine. Finally the target compounds, 6a-o, were prepared by reacting 4a-o with 5 in DMF and LiH. The final compounds were structurally elucidated by spectral data of IR, 1H-NMR and EI-MS. All the compounds were screened for their antibacterial evaluation and found to exhibit valuable results.
Aziz-Ur-Rehman,Ahtzaz, Samreen,Abbasi, Muhammad Athar,Siddiqui, Sabahat Zahra,Rasool, Shahid,Ahmad, Irshad
p. 3370 - 3375
(2017/05/22)

Synthesis and pharmacological screening: Sulfa derivatives of 2-pipecoline-bearing 1,3,4-oxadiazole core
An electrophile, 1-(4-(bromomethylbenzenesulfonyl)-2-methylpiperidine, was synthesized by the reaction of 2-methylpiperidine (2-pipecoline) and 4-bromomethylbenzenesulfonyl chloride in a weak basic medium under pH control. A series of nucleophiles, 5-aryl/aralkyl-1,3,4-oxadiazol-2-thiols, were synthesized from corresponding carboxylic acids in three steps. The title molecules were synthesized by coupling the electrophile to nucleophiles in an aprotic medium using LiH as an activator. The structures of all synthesized compounds were corroborated through IR, 1H NMR, and EI-MS techniques. All the compounds were screened for their pharmacological behavior, particularly, antibacterial and enzyme inhibitory activities. Notably efficient results were obtained against both gram-positive and gram-negative bacterial strains. Regarding enzyme inhibition, compounds were efficient against acetylcholinesterase and butyrylcholinesterase.
Aziz-ur-Rehman,Arif,Abbasi,Siddiqui,Rasool,Shah
p. 328 - 339
(2017/07/04)

Chemoselective nitro reduction and hydroamination using a single iron catalyst
The reduction and reductive addition (formal hydroamination) of functionalised nitroarenes is reported using a simple and bench-stable iron(iii) catalyst and silane. The reduction is chemoselective for nitro groups over an array of reactive functionalities (ketone, ester, amide, nitrile, sulfonyl and aryl halide). The high activity of this earth-abundant metal catalyst also facilitates a follow-on reaction in the reductive addition of nitroarenes to alkenes, giving efficient formal hydroamination of olefins under mild conditions. Both reactions offer significant improvements in catalytic activity and chemoselectivity and the utility of these catalysts in facilitating two challenging reactions supports an important mechanistic overlap.
Zhu, Kailong,Shaver, Michael P.,Thomas, Stephen P.
p. 3031 - 3035
(2016/05/24)

Competitive homolytic and heterolytic decomposition pathways of gas-phase negative ions generated from aminobenzoate esters
An alkyl-radical loss and an alkene loss are two competitive fragmentation pathways that deprotonated aminobenzoate esters undergo upon activation under mass spectrometric conditions. For the meta and para isomers, the alkyl-radical loss by a homolytic cleavage of the alkyl-oxygen bond of the ester moiety is the predominant fragmentation pathway, while the contribution from the alkene elimination by a heterolytic pathway is less significant. In contrast, owing to a pronounced charge-mediated ortho effect, the alkene loss becomes the predominant pathway for the ortho isomers of ethyl and higher esters. Results from isotope-labeled compounds confirmed that the alkene loss proceeds by a specific γ-hydrogen transfer mechanism that resembles the McLafferty rearrangement for radical cations. Even for the para compounds, if the alkoxide moiety bears structural motifs required for the elimination of a more stable alkene molecule, the heterolytic pathway becomes the predominant pathway. For example, in the spectrum of deprotonated 2-phenylethyl 4-aminobenzoate, m/z 136 peak is the base peak because the alkene eliminated is styrene. Owing to the fact that all deprotonated aminobenzoate esters, irrespective of the size of the alkoxy group, upon activation fragment to form an m/z 135 ion, aminobenzoate esters in mixtures can be quantified by precursor ion discovery mass spectrometric experiments.
Xia, Hanxue,Zhang, Yong,Pavlov, Julius,Jariwala, Freneil B.,Attygalle, Athula B.
p. 245 - 253
(2016/03/15)

Trinuclear {Co2+-M3+-Co2+} complexes catalyze reduction of nitro compounds
This work presents synthesis and characterization of trinuclear {Co2+-Co3+-Co2+} and {Co2+-Fe3+-Co2+} complexes with accessible peripheral Co(ii) ions. Both trinuclear complexes function as efficient reusable heterogeneous catalysts for the selective reduction of assorted nitro compounds to the corresponding amines. The mechanistic investigations suggest the involvement of a Co(ii)-Co(i) cycle in the catalysis.
Srivastava, Sumit,Dagur, Manvender S.,Ali, Afsar,Gupta, Rajeev
p. 17453 - 17461
(2015/10/19)

Design, synthesis and biological evaluation of novel sesquiterpene mustards as potential anticancer agents
Several novel series of sesquiterpene mustards (SMs) bearing nitrogen mustard and glutathione (GSH)-reactive α-methylene-γ-butyrolactone groups were successfully prepared for the first time and showed excellent antiproliferative activities in vitro. Among them, compounds 2e and 2g displayed the highest antiproliferative properties with IC50 values ranging from 2.5 to 8.7 μM. The selectivity of these two compounds was evaluated by SRB method against human cancer and normal hepatic cells (HepG2 and L02). The induction of apoptosis and effects on the cell cycle distribution with compounds 2e and 2g were investigated by Hoechst 33,258 staining and flow cytometry, which exhibited that they could induce selective cell apoptosis and cell cycle arrest in HepG2 and L02 cells. In addition, further investigation showed that compounds 2e and 2g could obviously inhibit the proliferation of HepG2 cells by inducing significant DNA cross-linking and depleting GSH in cell media. The good cytotoxicity and selectivity of compounds 2e and 2g pointed them as promising leads for anticancer drug design.
Xu, Yuan-Zhen,Gu, Xue-Yan,Peng, Shou-Jiao,Fang, Jian-Guo,Zhang, Ying-Mei,Huang, De-Jun,Chen, Jian-Jun,Gao, Kun
p. 284 - 297
(2015/03/30)

Synthesis of novel triazoles and a tetrazole of escitalopram as cholinesterase inhibitors
A novel serie of escitalopram triazoles (60-88) and a tetrazole (89) have been synthesized and subjected to a study to establish the inhibitory potential of these compounds toward acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). Some selectivity in inhibition has been observed. The 4-chlorophenyl- (75, IC50, 6.71 ± 0.25 μM) and 2-methylphenyl- (70, IC50, 9.52 ± 0.23 μM) escitalopram triazole derivatives depicted high AChE inhibition, while 2-fluorophenyl- (76, IC50 = 4.52 ± 0.17 μM) and 4-fluorophenyl- (78, IC50 = 5.31 ± 0.43 μM) have found to be excellent BChE inhibitors. It has also been observed that ortho, meta and para substituted electron donating groups increase the inhibition, while electron withdrawing groups reduce the inhibition. Docking analyses of inhibitors with AChE have depicted the binding energies for 70 and 75 as ΔGbind -6.42 and -6.93 kcal/mol, respectively, while ligands 76 and 78 have shown the binding affinity ΔGbind -9.04 and -8.51 kcal/mol, respectively, for BChE.
Mehr-Un-Nisa,Munawar, Munawar A.,Chattha, Fauzia A.,Kousar, Samina,Munir, Jawaria,Ismail, Tayaba,Ashraf, Muhammad,Khan, Misbahul A.
p. 6014 - 6024
(2015/11/11)

Iron and palladium(II) phthalocyanines as recyclable catalysts for reduction of nitroarenes
Iron(II) and palladium(II) phthalocyanines have been established as recyclable heterogeneous catalysts for the reduction of aromatic nitro compounds to corresponding amines using diphenylsilane/sodium borohydride as hydrogen sources in ethanol. Various reducible functional groups, such as acetyl, ester, cyano, amide, sulphonamide and carboxylic acid etc. were well tolerated, and the methods were applicable up to gram scale. Mechanistic studies showed that reduction of nitro group proceed through direct (nitroso) pathway and possibly iron or palladium phthalocyanines activates nitro group for reduction. FePc and PdPc also catalyzed the generation of hydrogen from the combination of diphenylsilane/sodium borohydride and ethanol.
Verma, Praveen Kumar,Bala, Manju,Thakur, Kavita,Sharma, Upendra,Kumar, Neeraj,Singh, Bikram
p. 1258 - 1267
(2014/07/21)

Facile method for the synthesis of oseltamivir phosphate
A ten-step scheme for the preparation of an antiviral agent, ethyl (3R,4R,5S)-4-acetylamino-5-amino-3-(pent-3-yloxy)cyclohex-1-enecarboxylate phosphate, from (-)-shikimic acid was studied. The main parameters of the synthesis were determined and the optimal conditions for the preparation of the intermediate compounds were selected. The total yield of oseltamivir phosphate calculated based on (-)-shikimic acid was 27%.
Kalashnikov,Sysolyatin,Sakovich,Sonina,Shchurova
p. 163 - 170
(2013/11/19)

γ-Amino butyric acid analogs as novel potent GABA-AT inhibitors: Molecular docking, synthesis, and biological evaluation
A new series, of γ-amino butyric acid analogs were designed and synthesized as novel potent GABA-AT inhibitors. A structure-activity relationship study was performed by correlating the effect of different substituents with GABA-AT inhibitory activity of the title compounds. The preliminary bioassays showed that acid hydrazones exhibited excellent inhibitory activities in micromolar (0.07-0.56 μM) range, while Schiff's bases showed variable results. The most potent compound, 4-amino-N'-[(1Z)-1-(2-bromophenyl) ethylidene]butanehydrazide (AHG177) showed inhibitory potency (IC50) of 0.073 μM. Aminobutyrate transaminase is a pyridoxal-P enzyme which follows a bi-bi ping pong mechanism and in pyridoxamine form can readily transaminate only with succinic semialdehyde and 2-oxoglutarate. The results strongly suggest that only the pyridoxal form of the enzyme is capable of reacting with the ligands. Our findings open up the possibility to extend this protocol to different databases in order to find new potential inhibitor for promising targets based on a rational drug design process.
Bansal,Sinha,Khosa
p. 134 - 146
(2013/03/13)

Development of triarylsulfonamides as novel anti-inflammatory agents
Triaylsulfonamides were identified as novel anti-inflammatory agents, acting by inhibition of RANKL and TNFα signaling. Structure-activity studies led to the identification of compounds with in vitro potencies of 50 >50 μM). A representative compound (4k, ABD455) was able to completely prevent inflammation in vivo in a prevention model and was highly effective at controlling inflammation in a treatment model.
Greig, Iain R.,Coste, Emmanuel,Ralston, Stuart H.,Van 'T Hof, Robert J.
supporting information
p. 816 - 820
(2013/03/14)

Synthesis and structure-activity relationship of (E)-phenoxyacrylic amide derivatives as Hypoxia-Inducible Factor (HIF) 1α inhibitors
A series of (E)-phenoxyacrylic amide derivatives were synthesized and evaluated as hypoxia inducible factor (HIF) 1α inhibitors. The present structure-activity relationship study on this series identified the morpholinoethyl containing ester 4p as a potent inhibitor of HIF-1α under hypoxic conditions (IC50 = 0.12 μM in a cell-based HRE reporter assay) in HCT116 cells. The representative compound 4p suppressed hypoxia-induced HIF-1α accumulation and targeted gene expression in a dose-dependent manner. The effect of HIF-1α inhibition by 4p was further demonstrated by its inhibitory activity on in vitro tube formation and migration of cells, which may be valuable for development of novel therapeutics for cancer and tumor angiogenesis.
Naik, Ravi,Won, Misun,Kim, Bo-Kyung,Xia, Yan,Choi, Hyun Kyung,Jin, Guanghai,Jung, Youngjin,Kim, Hwan Mook,Lee, Kyeong
supporting information
p. 10564 - 10571
(2013/02/22)

One-pot aromatic amination based on carbon-nitrogen coupling reaction between aryl halides and azido compounds
An efficient copper-mediated C-N coupling reaction between various aryl halides and azido compounds to produce the corresponding aromatic primary amines was established. The present amination is apparently involved in both the reduction of an azido functionality to the corresponding primary amino group and its cross-coupling reaction with aryl halides in a one-pot manner. The present amination could be applied to the synthesis of procaine, a local anesthetic drug. A mechanistic study indicated that 2-aminoethanol could work as a major hydrogen donor and the reaction would proceed without the formation of the intermediary aryl azide.
Maejima, Toshihide,Shimoda, Yutaka,Nozaki, Kei,Mori, Shigeki,Sawama, Yoshinari,Monguchi, Yasunari,Sajiki, Hironao
experimental part
p. 1712 - 1722
(2012/03/08)

Synthesis and cytotoxicity of some d-mannose click conjugates with aminobenzoic acid derivatives
Two sets of new conjugates obtained from d-mannose derivatives and o-, m-, and p-substituted benzoic acid esters interconnected through a triazole ring were synthesized by Cu(I) catalyzed azide-alkyne cycloaddition. All synthesized compounds were tested for their in vitro cytotoxic activity against seven cancer cell lines with/without multidrug resistance phenotype as well as non-tumor MRC-5 and BJ fibroblasts. Butyl ester of 4-aminobenzoic acid 6c showed the highest activity among all tested compounds, however, it was active only against K562 myeloid leukemia cells. N-Glycosyltriazole conjugates, both acetylated and nonacetylated at mannose moiety, were almost completely inactive. In contrast, some of the acetylated O-glycosyl conjugates showed cytotoxic activity which was cell line dependent and strongly affected by position of benzoic acid substitution as well as a length of its ester alkyl chain; the most potent compound was acetylated mannoside conjugated with octyl ester of m-substituted benzoic acid. However, deacetylation resulting in hydrophilicity increase of the glycosides almost completely abolished their cytotoxic potency.
Hradilová, Ludmila,Poláková, Monika,Dvo?áková, Barbora,Hajdúch, Marián,Petru?, Ladislav
p. 1 - 6
(2013/01/15)

Synthesis and bioactivity of novel adamantyl derivatives as potent MDR reversal agents
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Naik, Ravi,Jeon, Chanoh,Min, Hyeyoung,Choi, Hyun Kyung,Min, Kyung Hoon,Lee, Kyeong
scheme or table
p. 4444 - 4446
(2012/02/16)

Synthesis of symmetric diester-functionalised Troeger's base analogues
The yields of ester-functionalised Troeger's base analogues are dramatically improved by incorporating an electron-donating group on the aromatic ring and/or enhancing solubil- ity of the aniline unit. In addition to 2,8-diester compounds, 1,7-, 3,9- and 4,10-diester-functionalised Troeger's base analogues have been prepared for the first time.
Bhuiyan, M. Delower H.,Zhu, Kai-Xian,Jensen, Paul,Try, Andrew C.
supporting information; experimental part
p. 4662 - 4670
(2010/10/19)

Copper-mediated reductive amination of aryl halides with trimethylsilyl azide
(Chemical equation presented) Look, no azide! Trimethylsilyl azide was reductively cross-coupled with a variety of aryl halides in the presence of a copper species and amines, such as triethylamine or aminoethanol, to give the corresponding primary aryl amine in good yields without the formation of the expected aryl azide (see scheme).
Monguchi, Yasunari,Maejima, Toshihide,Mori, Shigeki,Maegawa, Tomohiro,Sajiki, Hironao
supporting information; experimental part
p. 7372 - 7375
(2010/08/20)

2-(Trimethylsilyl)ethanesulfonyl amide as a new ammonia equivalent for palladium-catalyzed amination of aryl halides
2-(Trimethylsilyl)ethanesulfonyl amide (SES-NH2) is an ammonia equivalent for the palladium-catalyzed amination of aryl bromides and aryl chlorides. Using these amine derivatives, it has been observed that anilines and anilines with sensitive functional groups can be readily prepared.
Anjanappa, Prakash,Mullick, Dibakar,Selvakumar, Kumaravel,Sivakumar, Manickam
p. 4585 - 4587
(2008/09/21)

BIPHENYL-4-YL-SULFONIC ACID ARYLAMIDES AND THEIR USE AS THERAPEUTIC AGENTS
The present invention pertains generally to the field of therapeutic compounds, and more specifically to certain aryl sulfonamides and related compounds (collectively referred to herein as "BPSAAA compounds"), as described herein, and including, for example, biphenyl-4-sulfonic acid (hydroxyalkyl-phenyl)-amides and related compounds. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, in treatment and/or prevention, for example, of inflammation and/or joint destruction and/or bone loss; of disorders mediated by excessive and/or inappropriate and/or prolonged activation of the immune system; of, inflammatory and autoimmune disorders, for example, rheumatoid arthritis, psoriasis, psoriatic arthritis, chronic obstructive pulmonary disease (COPD), atherosclerosis, inflammatory bowel disease, ankylosing spondylitis, and the like; of disorders associated with bone loss, such as bone loss associated with excessive osteoclast activation in rheumatoid arthritis, osteoporosis, cancer associated bone disease, Paget's disease and the like.
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Page/Page column 67

(2008/12/07)

N-Phenyl-N′-(2-chloroethyl)ureas (CEUs) as potential antineoplastic agents. Part 3: Role of carbonyl groups in the covalent binding to the colchicine-binding site
In the course of the development of N-phenyl-N′-(2-chloroethyl)ureas (CEUs) as potential antineoplastic agents, we investigated the effect of carbonylated substituting chains of the aromatic ring of CEU on their covalent binding to the colchicine-binding site (C-BS). In this study, we found that CEU, 5e, 5f, 8e, and 8f substituted by either a methyl ester or a methyl ketyl group at the ω-position exhibited a significant antiproliferative activity on HT-29, M21, and MCF-7 tumor cells. SDS-PAGE assays and cell cycle analysis confirmed that 5e, 5f, 8e, and 8f covalently bind to the C-BS and arrest the cell division in G2/M phase. Surprisingly, the presence of ω-carboxyl, ω-ethyl esters or ω-amides decreased significantly both the antiproliferative activity and the specificity toward β-tubulin.
Moreau, Emmanuel,Fortin, Sebastien,Lacroix, Jacques,Patenaude, Alexandre,Rousseau, Jean L.C.,C-Gaudreault, Rene
p. 1206 - 1217
(2008/09/18)

Synthesis of platensimycin analogues and their antibiotic potency
Platensimycin is a natural product isolated from various strains of Streptomyces platensis which exhibits antimicrobial activity against Gram positive bacteria, including vancomycin- and linezolide-resistant species. Analogues of platensimycin were synthesized from 3-aminobenzoic acid or other aniline derivatives and several alkyl- and aryl-carboxylic acids. The resulting compounds were tested in an agar diffusion assay against several bacteria and fungi.
Krauss, Juergen,Knorr, Veronika,Manhardt, Vera,Scheffels, Stefanie,Bracher, Franz
experimental part
p. 386 - 392
(2009/04/16)

Simple and efficient reduction of azides to amines using recyclable polymer-supported formate and zinc
Polymer supported formate in conjunction with commercial zinc dust provides a mild and efficient procedure for the reduction of organic azides to corresponding amines. A variety of alkyl and aryl azides were selectively reduced in high yield and purity at room temperature.
Prakasha, Kothathi C.,Sindhumol, Methatta,Ramesha Baba,Channe Gowda
p. 284 - 286
(2008/02/08)

A practical and selective reduction of nitroarenes using elemental sulfur and mild base
A method was developed to reduce aromatic nitro compounds to the corresponding anilines using sulfur and base. The method tolerates a range of functional groups on the benzene ring, avoids the use of hydrogen and transition metals and provides the anilines in moderate to high yields.
McLaughlin, Maureen A.,Barnes, David M.
p. 9095 - 9097
(2007/10/03)

Nitroarene reduction using Raney nickel alloy with ammonium chloride in water
Aromatic nitroarenes are reduced in high yields using a user-friendly combination of Raney nickel alloy and ammonium chloride in water at 80-90°C.
Bhaumik, Kankan,Akamanchi
p. 197 - 198
(2007/10/03)

Zinc/ammonium formate: A chemoselective and cost-effective protocol for the reduction of azides to amines
A variety of alkyl and aryl azides were selectively reduced in high yields to the corresponding amines by reaction with ammonium formate in the presence of low cost commercial zinc dust at room temperature.
Srinivasa,Nalina,Abiraj,Gowda, D. Channe
p. 630 - 631
(2007/10/03)

Cyclopentyl sulfonamide derivatives
The present invention provides certain cyclopentyl sulfonamide derivatives of formula (I): useful for potentiating glutamate receptor function in a mammal. It also relates to novel cyclopentyl sulfonamide derivatives, to processes for their preparation and to pharmaceutical compositions containing them.
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Page/Page column 35

(2010/01/31)

An efficient general method for esterification of aromatic carboxylic acids
Treatment of a variety of aromatic carboxylic acids with alcohols in the presence of thionyl chloride results in excellent yields of corresponding esters. This esterification system is compatible with a wide assortment of functional groups.
Hosangadi, Bhaskar D.,Dave, Rajesh H.
p. 6375 - 6378
(2007/10/03)

Angiotensin II receptor antagonists
Compounds are disclosed having the formula: STR1 The compounds of the invention are angiotensin II receptor antagonists.
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(2008/06/13)

Reduction of Aromatic Nitro Compounds with Baker's Yeast
The reduction of the nitro group of aromatic nitro compounds with baker's yeast was strongly influenced by the nature of the substituent on nitrobenzene, and in the reaction of acyl nitrobenzenes, selective reduction occurred to give optically active nitro alcohol and amino alcohol and amino ketone without giving any amino alcohol.Keywords baker's yeast; nitro compound; selective reduction; acyl nitrobenzene; chiral nitro alcohol
Takeshita, Mitsuhiro,Yoshida, Sachiko,Kiya, Rieko,Higuchi, Naoko,Kobayashi, Yumi
p. 615 - 617
(2007/10/02)

FACILE REDUCTION OF AROMATIC NITRO COMPOUNDS TO ANILINES WITH 2-PROPANOL AND RANEY NICKEL
2-Propanol in the presence of Raney nickel rapidly reduces aromatic nitro compounds to give the corresponding anilines.Reduction of the aromatic ring itself can generally be avoided by the judicious choice of the reaction time and temperature.Some substituent effects are noted.
Kuo, Elaine,Srivastava, S.,Cheung, C. K.,Noble, W. J. le
p. 599 - 602
(2007/10/02)

Polar Effects in Free Radical Reactions. Homolytic Aromatic Amination by the Amino Radical Cation, +NH3: Reactivity and Selectivity
Small amounts of Fe(II) salt initiate redox chains with hydroxyamino-O-sulfonic acid (HSA) and aromatic compounds leading to the amination of the aromatic ring.The positional and substrate selectivity with a variety of substituted benzenes show the important role of the electrophilic character of the radical +NH3.Hammett relationships with ? and ?+ are roughly observed.The lower sensitivity to polar effects of the radical +NH3 compared with (CH3)2+NH is explained by the different reaction enthalpies.The different positional selectivity obtained with anisole and the redox system +NH3OH/Ti(III) is discussed.
Citterio, Attilio,Gentile, Anna,Minisci, Francesco,Navarrini, Valter,Serravalle, Marco,Ventura, Susanna
p. 4479 - 4482
(2007/10/02)