cas 77987-49-6, BENZYL N-(2-HYDROXYETHYL)CARBAMATE

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Preparation method of N-(2-aminoethyl) morpholine
The invention provides a preparation method of N-(2-aminoethyl) morpholine, which comprises the following steps: S1, adding ethanolamine into dichloromethane to fully dissolve, dropwise adding benzyl chloroformate into the solution, and reacting under alkaline conditions to generate an intermediate 1; S2, adding the intermediate 1 into dichloromethane, fully dissolving, dropwise adding 4toluenesulfonyl chloride, and reacting under an alkaline condition to generate an intermediate 2; S3, adding the intermediate 2 into acetonitrile to be fully dissolved, adding morpholine into the acetonitrile to generate an intermediate 3, wherein the structural formula of the intermediate 3 is shown as the following formula (3); and S4, adding the intermediate 3 into methanol, fully dissolving, and carrying out a catalytic hydrogenation reaction under the action of a catalyst to generate N-(2-aminoethyl)morpholine. According to the N-(2-aminoethyl)morpholine preparation method provided by the embodiment of the invention, the raw materials used in the reaction are cheap and easily available, the toxicity is low, the operation is simple and convenient, and the method has less three wastes and is more environment-friendly.
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Paragraph 0062-0064; 0073-0075

(2021/04/21)

Oxyenamides as Versatile Building Blocks for a Highly Stereoselective One-Pot Synthesis of the 1,3-Diamino-2-ol-Scaffold Containing Three Continuous Stereocenters
A highly diastereoselective one-pot synthesis of the 1,3-diamino-2-alcohol unit bearing three continuous stereocenters is described. This method utilizes 2-oxyenamides as a novel type of building block for the rapid assembly of the 1,3-diamine scaffold containing an additional stereogenic oxygen functionality at the C2 position. A stereoselective preparation of the required (Z)-oxyenamides is reported as well.
Bolte, Michael,Grimmer, Jennifer,Kelm, Harald,Kramer, Philipp,Krieg, Sara-Cathrin,Manolikakes, Georg
supporting information
p. 23667 - 23671
(2021/09/30)

Interplay between a Foldamer Helix and a Macrocycle in a Foldarotaxane Architecture
The design and synthesis of a novel rotaxane/foldaxane hybrid architecture is reported. The winding of an aromatic oligoamide helix host around a dumbbell-shaped thread-like guest, or axle, already surrounded by a macrocycle was evidenced by NMR spectrosc
Gauthier, Maxime,Koehler, Victor,Clavel, Caroline,Kauffmann, Brice,Huc, Ivan,Ferrand, Yann,Coutrot, Frédéric
supporting information
p. 8380 - 8384
(2021/03/16)

PROCESS OF PREPARING ARACHIDONOYLETHANOLAMINE ANALOGUES
The present application provides new processes for preparing arachidonoylethanolamine analogues. Intermediates useful for preparing the compounds are also provided.
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Page/Page column 25

(2021/05/29)

Discovery of New Imidazo[2,1- b]thiazole Derivatives as Potent Pan-RAF Inhibitors with Promising in Vitro and in Vivo Anti-melanoma Activity
BRAF is an important component of MAPK cascade. Mutation of BRAF, in particular V600E, leads to hyperactivation of the MAPK pathway and uncontrolled cellular growth. Resistance to selective inhibitors of mutated BRAF is a major obstacle against treatment of many cancer types. In this work, a series of new (imidazo[2,1-b]thiazol-5-yl)pyrimidine derivatives possessing a terminal sulfonamide moiety were synthesized. Pan-RAF inhibitory effect of the new series was investigated, and structure-activity relationship is discussed. Antiproliferative activity of the target compounds was tested against the NCI-60 cell line panel. The most active compounds were further tested to obtain their IC50 values against cancer cells. Compound 27c with terminal open chain sulfonamide and 38a with a cyclic sulfamide moiety showed the highest activity in enzymatic and cellular assay, and both compounds were able to inhibit phosphorylation of MEK and ERK. Compound 38a was selected for testing its in vivo activity against melanoma. Cellular and animal activities are reported.
Abdel-Maksoud, Mohammed S.,El-Gamal, Mohammed I.,Lee, Bong S.,Gamal El-Din, Mahmoud M.,Jeon, Hong R.,Kwon, Dow,Ammar, Usama M.,Mersal, Karim I.,Ali, Eslam M. H.,Lee, Kyung-Tae,Yoo, Kyung Ho,Han, Dong Keun,Lee, Jae Kyun,Kim, Garam,Choi, Hong Seok,Kwon, Young Jik,Lee, Kwan Hyi,Oh, Chang Hyun
p. 6877 - 6901
(2021/06/25)

OLEOYLETHANOLAMIDE COMPOUNDS
The present application provides oleoylethanolamide compounds useful for treating a disease or disorder in a subject in need thereof. Pharmaceutical compositions comprising the compounds and methods of treating diseases or disorders are also provided.
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Page/Page column 43

(2021/10/02)

PALMITOYLETHANOLAMIDE COMPOUNDS
The present application provides palmitoylethanolamide compounds useful for treating a disease or disorder in a subject in need thereof. Pharmaceutical compositions comprising the compounds and methods of treating diseases or disorders are also provided.
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Page/Page column 43

(2021/10/02)

Solution-Phase Synthesis of Backbone-Constrained Cationic Peptoid Hexamers with Antibacterial and Anti-Biofilm Activities
Abstract: Submonomer synthesis in solution and block-coupling protocols were combined to prepare amphiphilic peptoid hexamers. The amphipathic character arises from the use of hydrophobic aliphatic tert-butyl side-chains imposing the cis-amide backbone co
Charbonnel, Nicolas,Faure, Sophie,Forestier, Christiane,Roy, Olivier,Shyam, Radhe,Taillefumier, Claude
supporting information
p. 5813 - 5822
(2021/11/17)

Design, synthesis and anticancer profile of new 4-(1H-benzo[d]imidazol-1-yl)pyrimidin-2-amine-linked sulfonamide derivatives with V600EBRAF inhibitory effect
A new series of 4-(1H-benzo[d]imidazol-1-yl)pyrimidin-2-amine linked sulfonamide derivatives 12a–n was designed and synthesized according to the structure of well-established V600EBRAF inhibitors. The terminal sulfonamide moiety was linked to the pyrimidine ring via either ethylamine or propylamine bridge. The designed series was tested at fixed concentration (1 μM) against V600EBRAF, finding that 12e, 12i and 12l exhibited the strongest inhibitory activity among all target compounds and 12l had the lowest IC50 of 0.49 μM. They were further screened on NCI 60 cancer cell lines to reveal that 12e showed the most significant growth inhibition against multiple cancer cell lines. Therefore, cell cycle analysis of 12e was conducted to investigate the effect on cell cycle progression. Finally, virtual docking studies was performed to gain insights for the plausible binding modes of vemurafenib, 12i, 12e and 12l.
Abdel-Maksoud, Mohammed S.,Mohamed, Ahmed A. B.,Hassan, Rasha M.,Abdelgawad, Mohamed A.,Chilingaryan, Garri,Selim, Samy,Abdel-Bakky, Mohamed S.,Al-Sanea, Mohammad M.
(2021/10/01)

Anticancer profile and anti-inflammatory effect of new N-(2-((4-(1,3-diphenyl-1H-pyrazol-4-yl)pyridine sulfonamide derivatives
A new series of N-(2-((4-(1,3-diphenyl-1H-pyrazol-4-yl)pyridine sulfonamide derivatives 11a-o were designed and synthesized based on our previous works. The new series was tested for its anticancer and anti-inflammatory effects. The anticancer profile of
Abdel-Maksoud, Mohammed S.,Mohamed Hassan, Rasha,Abdel-Sattar El-Azzouny, Aida,Nabil Aboul-Enein, Mohamed,Oh, Chang-Hyun
(2021/10/25)

IDEBENONE COMPOUNDS
The present application provides idebenone derivatives or analogues useful for treating a disease or disorder in a subject in need thereof. Pharmaceutical compositions comprising the compounds and methods of treating the disease or disorder are also provided.
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Page/Page column 58

(2021/10/22)

Me3SI-promoted chemoselective deacetylation: a general and mild protocol
A Me3SI-mediated simple and efficient protocol for the chemoselective deprotection of acetyl groups has been developedviaemploying KMnO4as an additive. This chemoselective deacetylation is amenable to a wide range of substrates, tolerating diverse and sensitive functional groups in carbohydrates, amino acids, natural products, heterocycles, and general scaffolds. The protocol is attractive because it uses an environmentally benign reagent system to perform quantitative and clean transformations under ambient conditions.
Gurawa, Aakanksha,Kashyap, Sudhir,Kumar, Manoj
p. 19310 - 19315
(2021/06/03)

Design, physico-chemical characterization andin vitrobiological activity of organogold(iii) glycoconjugates
To develop new metal-based glycoconjugates as potential anticancer agents, four organometallic gold(iii)-dithiocarbamato glycoconjugates of the type [AuIII(2-Bnpy)(SSC-Inp-GlcN)](PF6) (2-Bnpy: 2-benzylpyridine; Inp: isonipecotic moie
Pettenuzzo, Andrea,Vezzù, Keti,Di Paolo, Maria Luisa,Fotopoulou, Eirini,Marchiò, Luciano,Via, Lisa Dalla,Ronconi, Luca
supporting information
p. 8963 - 8979
(2021/07/02)

Oligosaccharide-camptothecin conjugates as potential antineoplastic drugs: Design, synthesis and biological evaluation
Thirty novel 20 (S)–O-linked camptothecin (CPT) glycoconjugates were synthesized. They showed more potent in vitro cytotoxicities over irinotecan, but very weak direct topoisomerase I (Topo I) inhibition was observed at 100.0 μM. Oligosaccharide types, length of a PEG linker and acetyl groups exerted obvious effects on cytotoxicity, selectivity, water solubility and stability of the newly synthesized CPT glycoconjugates. Construct 40, with a bleomycin (BLM) disaccharide linked to diethylene glycol in the introduced ester moiety, demonstrated a superior antitumor activity and a distinct selectivity compared to CPT. No toxicity was detectable in animal acute toxicity intravenously (160 mg/kg). Collectively, attachment of oligosaccharides with tumor targeting to 20 (S)–OH of CPT could offer a solution to the daunting problems posed by current Topo I poisons.
Li, Maolin,Ye, Wenchong,Fu, Kaishuo,zhou, Cui,Shi, Yonghui,Huang, Weiping,Chen, Wenming,Hu, Jiliang,Jiang, Zhilin,Zhou, Wen
(2020/07/15)

ANANDAMIDE COMPOUNDS
The present application provides anandamide and 2-arachidonyl glycerol compounds useful for treating a disease or disorder in a subject in need thereof. Pharmaceutical compositions comprising the compounds and methods of treating diseases or disorders are also provided.
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Page/Page column 41

(2020/07/25)

Imidazothiazole-based potent inhibitors of V600E-B-RAF kinase with promising anti-melanoma activity: biological and computational studies
A series of imidazothiazole derivatives possessing potential activity against melanoma cells were investigated for molecular mechanism of action. The target compounds were tested against V600E-B-RAF and RAF1 kinases. Compound 1zb is the most potent agains
Anbar, Hanan S.,El-Gamal, Mohammed I.,Jeon, Hong R.,Kwon, Dow,Lee, Bong S.,Oh, Chang-Hyun,Tarazi, Hamadeh
p. 1712 - 1726
(2020/10/02)

Design and synthesis of novel pyrrolo[2,3-b]pyridine derivatives targeting V600EBRAF
Several pyrrolo[2,3-b]pyridine-based B-RAF inhibitors are well known and some of them are currently FDA approved as anticancer agents. Based on the structure of these FDA approved V600EB-RAF inhibitors, two series of pyrrolo[2,3-b]pyridine scaffold were designed and synthesized in attempt to develop new potent V600EB-RAF inhibitors. The 38 synthesized compounds were biologically evaluated for their V600EB-RAF inhibitory effect at single dose (10 μM). Compounds with high percent inhibition were tested to determine their IC50 over V600EB-RAF. Compounds 34e and 35 showed the highest inhibitory effect with IC50 values of 0.085 μM and 0.080 μM, respectively. Headed for excessive biological evaluation, the synthesized derivatives were tested over sixty diverse human cancer cell lines. Only compound 35 emerged as a potent cytotoxic agent against different panel of human cancer cell lines.
Abdel-Maksoud, Mohammed S.,Ali, Eslam M. H.,Ammar, Usama M.,Mersal, Karim I.,Oh, Chang-Hyun,Yoo, Kyung Ho
(2020/04/28)

Novel pleuromutilin derivatives with substituted 6-methylpyrimidine: Design, synthesis and antibacterial evaluation
A series of novel pleuromutilin derivatives with substituted 6-methylpyrimidine moieties was designed, synthesized, and evaluated for their antibacterial activities. Most of the tested compounds exhibited potent antibacterial activities against Staphyloco
Cheng, Feng,Fan, Yuan,Hao, Baocheng,Liu, Yu,Shang, Ruofeng,Shi, Tao,Wang, Hao,Yi, Yunpeng
(2020/08/22)

Method for preparing 3-ketomorpholine
The invention relates to a method for preparing 3-ketomorpholine. The method comprises the following steps: protecting the amino group of ethanolamine firstly, then carrying out a reaction of amino group protected ethanolamine with alkyl haloacetate, performing deprotection on the prepared product, and performing ring closure so as to obtain 3-ketomorpholine. The method has the advantages of simple practical operation, low equipment requirements, high yield and low three waste, and is suitable for industrial large-scale production.
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Paragraph 0034; 0042; 0043-; 0072-0074

(2019/03/26)

Camptothecin sugar derivative and preparation method and application thereof
The invention relates to a camptothecin sugar derivative and a preparation method and application thereof, and belongs to the field of biological medicines. The structural formula of the camptothecinsugar derivative is shown in formula (I) in specification. The camptothecin sugar derivative can obviously improve the stability and water solubility of camptothecin and 10-hydroxycamptothecin, and has different sensitivities to different tumor cells. Especially when the chain link n equals to 1, the camptothecin sugar derivative of the invention can significantly increase the selectivity to tumorcells.
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Paragraph 0054-0057

(2019/11/13)

Synthesis method of double different protected amino acids
The invention relates to a synthesis method of double different protected amino acids.The technical problems of harsh reaction conditions, inapplicability of production enlarging and the like in an existing synthesis method are mainly solved. According to the technical scheme, the synthesis method of double different protected amino acids comprises the following steps: one of Boc20, Alloc-Cl or Cbz-Osuis added to amino alcohol under the action of an alkaline reagent to obtain a compound 1; the compound 1 reacts with methanesulfonyl chloride or paratoluensulfonyl chloride to obtain an intermediate, then a halide is added into acetone, heating and refluxing are executed to obtain a compound 2; the compound 2 is condensed with diethyl acetamidomalonate under the action of an alkaline agent togenerate a compound 3; the compound 3 is dissolved in alcohol and water, an inorganic base is added, heating, hydrolyzing and decarboxylating are executed to obtain a compound 4; acetylase is added into deionized water to obtain a compound 5 through enzymolysis; amino acid protection is executed, wherein one of Fmoc-Osu, Cbz-OSu, Alloc-Cl or Boc20 is added into thecompound 5 under the action of an alkaline agent to generatea target compound A.
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Paragraph 0020

(2019/07/04)

Staudinger/aza-Wittig reaction to access Nβ-protected amino alkyl isothiocyanates
A unified approach to access Nβ-protected amino alkyl isothiocyanates using Nβ-protected amino alkyl azides through a general strategy of Staudinger/aza-Wittig reaction is described. The type of protocol used to access isothiocyanates depends on the availability of precursors and also, especially in the amino acid chemistry, on the behavior of other labile groups towards the reagents used in the protocols; fortunately, we were not concerned about both these factors as precursor-azides were prepared easily by standard protocols, and the present protocol can pave the way for accessing title compounds without affecting Boc, Cbz and Fmoc protecting groups, and benzyl and tertiary butyl groups in the side chains. The present strategy eliminates the need for the use of amines to obtain title compounds and thus, this method is step-economical; additional advantages include retention of chirality, convenient handling and easy purification. A few hitherto unreported compounds were also prepared, and all final compounds were completely characterized by IR, mass, optical rotation, and 1H and 13C NMR studies.
Santhosh,Durgamma,Shekharappa,Sureshbabu, Vommina V.
p. 4874 - 4880
(2018/07/15)

Modular One-Step Three-Component Synthesis of Tetrahydroisoquinolines Using a Catellani Strategy
Reported is a modular one-step three-component synthesis of tetrahydroisoquinolines using a Catellani strategy. This process exploits aziridines as the alkylating reagents, through palladium/norbornene cooperative catalysis, to enable a Catellani/Heck/aza-Michael addition cascade. This mild, chemoselective, and scalable protocol has broad substrate scope (43 examples, up to 90 % yield). The most striking feature of this protocol is the excellent regioselectivity and diastereoselectivity observed for 2-alkyl- and 2-aryl-substituted aziridines to access 1,3-cis-substituted and 1,4-cis-substituted tetrahydroisoquinolines, respectively. Moreover, this is a versatile process with high step and atom economy.
Qian, Guangyin,Bai, Miao,Gao, Shijun,Chen, Han,Zhou, Siwei,Cheng, Hong-Gang,Yan, Wei,Zhou, Qianghui
supporting information
p. 10980 - 10984
(2018/07/30)

Synthetic method of chiral piperazidone derivative
The invention relates to a synthetic method of a chiral piperazidone derivative. The synthetic method comprises the following steps: performing an oxidation reaction on ethanolamine with a protectivegroup in a formula (I) to obtain aminoacetaldehyde with a protective group in a formula (II); in an alcohol solvent, performing a reduced amination reaction on the aminoacetaldehyde with the protective group in the formula (II) and amino acid ester in the presence of a reducing agent to obtain the chiral piperazidone derivative in the formula (II), wherein the reduced amination reaction temperature is -10 DEG C to 0 DEG C, and the amino acid ester is L-type amino acid ester or D-type amino acid ester; and in the alcohol solvent, performing a de-protection reaction on the chiral piperazidone derivative in the formula (II) and forming a ring to obtain a chiral piperazidone derivative in a formula (IV), wherein a reaction route is shown as follows: the protective group X is benzoxo carbonyl or tert-butyoxo carbonyl; R is methyl, ethyl, isopropyl, isobutyl, hydroxyethyl, benzyl, p-hydroxybenzyl and the like; and R' is methyl, ethyl and the like.
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Paragraph 0068; 0074; 0075; 0100; 0101

(2018/07/06)

BIPOLAR TETRAETHER LIPIDS
Disclosed herein, inter alia, are compounds, compositions, and liposomes and methods of thereof.
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Paragraph 0029; 0537

(2017/03/21)

CONJUGATES COMPRISING SELF-IMMOLATIVE GROUPS AND METHODS RELATED THERETO
In some aspects, the invention relates to an antibody-drug conjugate, comprising an antibody; a linker; and an active agent. The antibody-drug conjugate may comprise a self- immolative group. The linker may comprise an O-substituted oxime, e.g., wherein the oxygen atom of the oxime is substituted with a group that covalently links the oxime to the active agent; and the carbon atom of the oxime is substituted with a group that covalently links the oxime to the antibody.
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Page/Page column 68

(2017/06/27)

CONJUGATES COMPRISING PEPTIDE GROUPS AND METHODS RELATED THERETO
In some aspects, the invention relates to an antibody-drug conjugate, comprising an antibody; a linker; and at least two active agents. In preferred embodiments, the linker comprises a peptide sequence of a plurality of amino acids, and at least two of the active agents are covalently coupled to side chains of the amino acids. The antibody-drug conjugate may comprise a self-immolative group, preferably two-self-immolative groups. The linker may comprise an O-substituted oxime, e.g., wherein the oxygen atom of the oxime is substituted with a group that covalently links the oxime to the active agent; and the carbon atom of the oxime is substituted with a group that covalently links the oxime to the antibody.
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Page/Page column 78; 79

(2017/08/08)

Broad-spectrum antiproliferative activity of a series of 6-(4-fluorophenyl)-5-(2-substituted pyrimidin-4-yl)imidazo[2,1-b]thiazole derivatives
This article described the synthesis and in vitro antiproliferative activities a series of 6-(4-fluorophenyl)-5-(2-substituted pyrimidin-4-yl)imidazo[2,1-b]thiazole derivatives. The nine target compounds were tested for in vitro antitumor effect against a
Abdel-Maksoud, Mohammed S.,El-Gamal, Mohammed I.,Gamal El-Din, Mahmoud M.,Kwak, Seong-Shin,Kim, Hyun-Il,Oh, Chang-Hyun
p. 824 - 833
(2016/04/20)

Insights into the Pummerer synthesis of oxazolines
A rapid and simple method to access unnatural 2-substituted 5-thio oxazolines has been developed. This methodology is based on a Pummerer reaction followed by an intramolecular nucleophilic substitution, which changes the paradigm for the normal use of a base in Pummerer chemistry. We also provide a useful two-step method for the synthesis of the starting material and a mechanistic proposal based on experimental observations, which contests the previously proposed reaction pathway. The reaction proved to be general, and different substituents, such as alkyl, aryl, alkenyl and functionalized groups, can be used without a significant decrease in efficiency.
Becerra-Cely, Laura,Rueda-Espinosa, Juan,Ojeda-Porras, Andrea,Gamba-Sánchez, Diego
p. 8474 - 8485
(2016/09/28)

Design, synthesis, and in vitro antiproliferative and kinase inhibitory effects of pyrimidinylpyrazole derivatives terminating with arylsulfonamido or cyclic sulfamide substituents
A novel series of substituted pyrimidine compounds bearing N-phenylpyrazole and terminating with aryl and cyclic sulfonamido moiety were designed, synthesized, and evaluated in vitro as antiproliferative agents against a panel of 53 cell lines of differen
Gamal El-Din, Mahmoud M.,El-Gamal, Mohammed I.,Abdel-Maksoud, Mohammed S.,Yoo, Kyung Ho,Baek, Daejin,Choi, Jungseung,Lee, Huiseong,Oh, Chang-Hyun
p. 111 - 122
(2016/12/14)

Effect of Headgroups on Small-Ion Permeability across Archaea-Inspired Tetraether Lipid Membranes
This paper examines the effects of four different polar headgroups on small-ion membrane permeability from liposomes comprised of Archaea-inspired glycerolmonoalkyl glycerol tetraether (GMGT) lipids. We found that the membrane-leakage rate across GMGT lipid membranes varied by a factor of ≤1.6 as a function of headgroup structure. However, the leakage rates of small ions across membranes comprised of commercial bilayer-forming 1-palmitoyl-2-oleoyl-sn-glycerol (PO) lipids varied by as much as 32-fold within the same series of headgroups. These results demonstrate that membrane leakage from GMGT lipids is less influenced by headgroup structure, making it possible to tailor the structure of the polar headgroups on GMGT lipids while retaining predictable leakage properties of membranes comprised of these tethered lipids. Extremophiles require robust membranes with low ion permeability to survive in harsh conditions. These Archaea organisms achieve low membrane permeability, in part, by generating lipids with unusual structural features such as tethering of their lipid tails. A systematic study probing the effect of polar headgroups in synthetic Archaea-inspired lipids showed little dependence of membrane leakage rates of small ions as a function of headgroup structure.
Koyanagi, Takaoki,Leriche, Geoffray,Yep, Alvin,Onofrei, David,Holland, Gregory P.,Mayer, Michael,Yang, Jerry
supporting information
p. 8074 - 8077
(2016/06/14)

ISOINDOLIN-1-ONES AS MACROPHAGE MIGRATION INHIBITORY FACTOR (MIF) INHIBITORS
Compounds having an isoindolin-1-one backbone of Formula (I) are disclosed which have utility in treating and/or preventing microbial infections, tumor growth, metastasis and other macrophage migration inhibitory factor (MIF)-modulated pathological condit
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Paragraph 0320; 0321; 0322

(2015/07/02)

Synthesis and evaluation of protein arginine N-methyltransferase inhibitors designed to simultaneously occupy both substrate binding sites
The protein arginine N-methyltransferases (PRMTs) are a family of enzymes that function by specifically transferring a methyl group from the cofactor S-adenosyl-l-methionine (AdoMet) to the guanidine group of arginine residues in target proteins. The most notable is the PRMT-mediated methylation of arginine residues that are present in histone proteins which can lead to chromatin remodelling and influence gene transcription. A growing body of evidence now implicates dysregulated PRMT activity in a number of diseases including various forms of cancer. The development of PRMT inhibitors may therefore hold potential as a means of developing new therapeutics. We here report the synthesis and evaluation of a series of small molecule PRMT inhibitors designed to simultaneously occupy the binding sites of both the guanidino substrate and AdoMet cofactor. Potent inhibition and surprising selectivity were observed when testing these compounds against a panel of methyltransferases.
Van Haren, Matthijs,Van Ufford, Linda Quarles,Moret, Ed E.,Martin, Nathaniel I.
p. 549 - 560
(2015/02/02)

N-Urethane protection of amines and amino acids in an ionic liquid
An efficient, solvent-free protocol for the N-fluorenylmethoxycarbonylation and N-benzyloxycarbonylation of amines is described. The reaction of aliphatic and aromatic amines with FmocOSu and Cbz-Osu in [Bmim][BF4] at room temperature afforded the corresponding N-urethane derivatives in excellent yields and do not require any further purification. The method has been extended to the N-Fmoc and N-Cbz protection of amino acids. Absence of bases, very short reaction times, high yields, selectivity and ease of product separation are some advantages of this protocol.
Di Gioia,Gagliardi,Leggio,Leotta,Romio,Liguori
p. 63407 - 63420
(2015/08/11)

Synthesis of Nα-Z protected amino alkyl triazole acids and their application to neo-glycopeptides synthesis
The synthesis of triazole linked glycopeptides employing 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) mediated coupling of Z-protected triazole acids with glycosyl amines and amino acid esters is described. The coupling proceeded smoothly at room temperat
Madhu, Chilakapati,Panguluri, Nageswara Rao,Sureshbabu, Vommina V.
p. 858 - 864
(2014/08/05)

NOVEL OXAZOLIDINONE DERIVATIVE AND MEDICAL COMPOSITION CONTAINING SAME
Disclosed is a novel oxazolidinone derivative represented by Formula 1 above, in particular, a novel oxazolidinone compound having a cyclic amidoxime or cyclic amidrazone group. In Formula 1, R and Q are the same as defined in the detailed description. In addition, disclosed is a pharmaceutical composition for an antibiotic which includes the novel oxazolidinone derivative of Formula 1, a prodrug thereof, a hydrate thereof, a solvate thereof, an isomer thereof, or a pharmaceutically acceptable salt thereof as an active ingredient. The novel oxazolidinone derivative, the prodrug thereof, the hydrate thereof, the solvate thereof, the isomer thereof, and the pharmaceutically acceptable salt thereof have broad antibacterial spectrum against resistant bacteria, low toxicity and strong antibacterial effects against Gram-positive and Gram-negative bacteria and thus may be effectively used as antibiotics.
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Paragraph 0085-0086

(2014/02/16)

NOVEL OXAZOLIDINONE DERIVATIVE AND MEDICAL COMPOSITION CONTAINING SAME
Disclosed is a novel oxazolidinone derivative represented by Formula 1 above, in particular, a novel oxazolidinone compound having a cyclic amidoxime or cyclic amidrazone group. In Formula 1, R and Q are the same as defined in the detailed description. In addition, disclosed is a pharmaceutical composition for an antibiotic which includes the novel oxazolidinone derivative of Formula 1, a prodrug thereof, a hydrate thereof, a solvate thereof, an isomer thereof, or a pharmaceutically acceptable salt thereof as an active ingredient. The novel oxazolidinone derivative, the prodrug thereof, the hydrate thereof, the solvate thereof, the isomer thereof, and the pharmaceutically acceptable salt thereof have broad antibacterial spectrum against resistant bacteria, low toxicity and strong antibacterial effects against Gram-positive and Gram-negative bacteria and thus may be effectively used as antibiotics.
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Paragraph 0095-0097

(2014/07/08)

Compounds for the protection of sulfur containing linkers in nucleic acid synthesis
Aromatic and alkyl thiocarbonates with and without a neighboring group that participates in the hydrolysis of a thiocarbonate are described. The aromatic or alkyl thiocarbonates can be used for the protection of sulfur during oligonucleotide synthesis. Th
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Page/Page column 18

(2014/03/26)

NOVEL CEPHALOSPORIN DERIVATIVE AND PHARMACEUTICAL COMPOSITION THEREOF
The present invention relates to novel cephalosporin derivatives represented by Chemical Formula 1. Wherein, X, Y, L, R1, and R2 are as same as defined in the description of the invention. The present invention also relates to pharmaceutical antibiotic compositions comprising a novel celphalosporin derivative represented by Chemical Formula 1, a prodrug thereof, a hydrate thereof, a solvate thereof, an isomer thereof, or a pharmaceutically acceptable salt thereof as an effective ingredient. According to the present invention, novel cephalosporin derivatives, a prodrug thereof, a hydrate thereof, a solvate thereof, an isomer thereof, or a pharmaceutically acceptable salt thereof as an effective ingredient for the broad spectrum of antibiotic resistant, low toxicity, particularly in Gram-negative bacteria, which can be useful with strong antimicrobial activity.
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Paragraph 0083

(2014/03/25)

Reductive removal of methoxyacetyl protective group using sodium borohydride
Herein, we have developed a mild and selective reductive deprotection method for the MAc protected alcohols using sodium borohydride. The new deprotection conditions provide a complete orthogonality between O-MAc and other protecting groups such as tert-butyl ester, N-Boc, Fmoc, Cbz, O-TBDMS, N-benzyl, O-benzyl, O-acetyl, N-acetyl, N-MAc, etc. In addition to O-MAc deprotection, this method is also applicable for S-MAc deprotection.
Gadekar, Pradip K.,Hoermann, Maryann,Corbo, Faith,Sharma, Rajiv,Sarveswari,Roychowdhury, Abhijit
p. 503 - 506
(2014/01/06)

A facile protocol for N-Cbz protection of amines in PEG-600
An efficient and eco-friendly protocol for the chemoselective N-benzyloxycarbonylation of amines was described. The reaction of amines with benzyl chloroformate (Cbz-Cl) in the presence of PEG-600 at room temperature afforded the corresponding N-Cbz derivatives in excellent yields. The method is applicable to the N-Cbz protection of aliphatic (acyclic and cyclic) and aromatic amines.
Zhang, Chun Lin,Zhang, Dong Feng,Zhao, Hong Yi,Lin, Zi Yun,Huang, Hai Hong
experimental part
p. 789 - 792
(2012/08/08)

NOVEL CEPHALOSPORIN DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS THEREOF
The present invention relates to novel cephalosporin derivatives represented by Chemical Formula 1. Wherein, X, Y, L, R1, and R2 are as same as defined in the description of the invention. The present invention also relates to pharmaceutical antibiotic compositions comprising a novel celphalosporin derivative represented by Chemical Formula 1, a prodrug thereof, a hydrate thereof, a solvate thereof, an isomer thereof, or a pharmaceutically acceptable salt thereof as an effective ingredient. According to the present invention, novel cephalosporin derivatives, a prodrug thereof, a hydrate thereof, a solvate thereof, an isomer thereof, or a pharmaceutically acceptable salt thereof as an effective ingredient for the broad spectrum of antibiotic resistant, low toxicity, particularly in Gram-negative bacteria, which can be useful with strong antimicrobial activity.
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Page/Page column 36

(2012/10/23)

Synthesis of N-vinyloxazolidinones and morpholines from amino alcohols and vinylsulfonium salts: Analysis of the outcome's dependence on the N-protecting group by nanospray mass spectrometry
The effect of the nature of the N-protecting group on 1,2-amino alcohols in annulation reactions with diphenylvinylsulfonium triflate has been investigated. Although tosyl and sulfinamide groups give morpholines in high yields, the use of N-Cbz leads to a high-yielding synthesis of N-vinyloxazolidinones. The reactions were monitored by nanospray MS/MS, which revealed why reactions are successful and the fate of reactive intermediates in the unsuccessful reactions.
Yar, Muhammad,Fritz, Sven P.,Gates, Paul J.,McGarrigle, Eoghan M.,Aggarwal, Varinder K.
supporting information; experimental part
p. 160 - 166
(2012/02/04)

An efficient and facile synthesis of N-Cbz-β-aminoalkanesulfonamides
An efficient method for the synthesis of N-Cbz-β- aminoalkanesulfonamides was described. N-Cbz-β-aminoalkanesulfona-mides were readily prepared in good yields from a variety of amino alcohols, including optically active ones, via N-Cbz protection with ben
Meng, Fanhua,Chen, Ning,Xu, Jiaxi
p. 2548 - 2553
(2013/06/27)

Carboxyalkyl peptoid PNAs: Synthesis and hybridization properties
Nγ-Carboxyalkyl modified peptide nucleic acids (PNAs), containing the four canonical nucleobases, were prepared via solid-phase oligomerization. The inserted peptoid monomers 1 and 2 were constructed through simple synthetic procedures, utilizi
De Cola, Chiara,Manicardi, Alex,Corradini, Roberto,Izzo, Irene,De Riccardis, Francesco
experimental part
p. 499 - 506
(2012/01/14)

Bromodimethyl sulfonium bromide mediated rapid and facile protection of amines
A new clean protocol for protection of aryl and aliphatic amines with t-butoxycarbonyl (t-BOC) and benzyloxycarbonyl (Cbz) catalyzed by simple (bromodimethyl) sulfonium bromide has been developed. Rapid protection of amines in excellent yields in totally solvent-free conditions has been achieved. Copyright
Shailaja,Manjula,Vittal Rao
experimental part
p. 2073 - 2080
(2011/07/31)

New imidazo[2,1-b]thiazole derivatives: Synthesis, in vitro anticancer evaluation, and in silico studies
A series of 18 new imidazo[2,1-b]thiazole derivatives was synthesized. Their in vitro antiproliferative activities against A375P human melanoma cell line and NCI-60 cell line panel were tested. Compounds 15, 16, 18, 22, 26-28, and 31 showed superior poten
Park, Jin-Hun,El-Gamal, Mohammed I.,Lee, Yong Sup,Oh, Chang-Hyun
experimental part
p. 5769 - 5777
(2012/01/05)

Synthesis of new 6-(4-Fluorophenyl)-5-(2-substituted pyrimidin-4-yl) imidazo[2,1-b] thiazole derivatives and their antiproliferative activity against melanoma cell line
Synthesis of a new series of pyrimidinyl-imidazo[2,1-b]thiazole derivatives is described. Their antiproliferative activity against A375 human melanoma cell line was tested and the effect of substituents on the pyrimidinyl ring side chain was investigated.
Park, Jin-Hun,Oh, Chang-Hyun
experimental part
p. 2854 - 2860
(2012/04/17)

Carbamate derivatives of felbamate as potential anticonvulsant agents
Several monocarbamate compounds derived from felbamate were synthesized and 11 target compounds (1, 4, and 6-14) were initially evaluated in mice MES and PTZ models in our laboratory. Carbamate compounds with varying substituents on the oxygen (1-4) gave anticonvulsant activity with a wide range of ED 50 in MES test from 300 mg/kg (4) and compounds with different groups on the nitrogen (5-14) also were quite active in the range of 15 mg/kg (14) to 170.5 mg/kg (6). This suggested that the spatial limitation in the MES model seemed flexible especially on the nitrogen end. All tested compounds showed some activity against mice scPTZ test, but none had the ED50 value 50 mg/kg. Ten selected compounds (1 and 6-14) for subsequent pharmacological evaluation in NIH all gave positive mice MES activity except 8 and 9, which were unexpectedly active in rats after further evaluations. Among the compounds, 1, 8, and 9 advanced to the quantitative study and 1 and 9 provided the highest PI values, 15 and 21, respectively, in the rat oral MES test.
Kung, Ching-Hsin,Kwon, Chul-Hoon
experimental part
p. 498 - 513
(2011/03/19)

Virtual screening, selection and development of a benzindolone structural scaffold for inhibition of lumazine synthase
Virtual screening of a library of commercially available compounds versus the structure of Mycobacterium tuberculosis lumazine synthase identified 2-(2-oxo-1,2-dihydrobenzo[cd]indole-6-sulfonamido)acetic acid (9) as a possible lead compound. Compound 9 proved to be an effective inhibitor of M. tuberculosis lumazine synthase with a Ki of 70 μM. Lead optimization through replacement of the carboxymethylsulfonamide sidechain with sulfonamides substituted with alkyl phosphates led to a four-carbon phosphate 38 that displayed a moderate increase in enzyme inhibitory activity (Ki 38 μM). Molecular modeling based on known lumazine synthase/inhibitor crystal structures suggests that the main forces stabilizing the present benzindolone/enzyme complexes involve π-π stacking interactions with Trp27 and hydrogen bonding of the phosphates with Arg128, the backbone nitrogens of Gly85 and Gln86, and the side chain hydroxyl of Thr87.
Talukdar, Arindam,Morgunova, Ekaterina,Duan, Jianxin,Meining, Winfried,Foloppe, Nicolas,Nilsson, Lennart,Bacher, Adelbert,Illarionov, Boris,Fischer, Markus,Ladenstein, Rudolf,Cushman, Mark
experimental part
p. 3518 - 3534
(2010/08/05)