- Nanoceria as an efficient and green catalyst for the chemoselective N-tert-butyloxycarbonylation of amines under the solvent-free conditions
-
Nanocerium oxide mediated an efficient and green protocol has been described for the chemoselective N-tert-butyloxycarbonylation of amines under the solvent-free conditions at ambient temperature. Various aliphatic, aromatic and heteroaromatic amines were protected using developed protocol and several functional groups such as alcohol, phenol and ester were well tolerated under these conditions. The rapid reaction rate, mild conditions, very good functional group tolerance, excellent yield, solvent-free, easy recovery products and excellent catalyst recyclability are the advantages of this protocol. This makes the protocol feasible, economical and environmentally benign.
- Garad, Dnyaneshwar N.,Ingale, Ajit P.,Shinde, Sandeep V.,Ukale, Dattatraya
-
supporting information
p. 1656 - 1668
(2021/04/05)
-
- Sulfated tungstate: A highly efficient, recyclable and ecofriendly catalyst for chemoselective N-tert butyloxycarbonylation of amines under the solvent-free conditions
-
Sulfated tungstate catalyzed an efficient and ecofriendly protocol has been described for the chemoselective N-tert-butyloxycarbonylation of amines under the solvent-free conditions at room temperature. The variety of functionalized aliphatic, aromatic and heteroaromatic amines efficiently undergoes the N-tert-butyloxycarbonylation under the developed protocol. The aminoalcohol, aminophenol, aminoester as well as various chiral amines underwent the chemoselective N-Boc protection under the optimized reaction condition. The rapid reaction rate, mild conditions, very good functional group tolerance, excellent yield, solvent-free, easy recovery products and excellent catalyst recyclability are the advantages of this protocol. This makes the protocol feasible, economical and environmentally benign.
- Ingale, Ajit P.,Shinde, Sandeep V.,Thorat, Nitin M.
-
supporting information
p. 2528 - 2543
(2021/07/02)
-
- Ultrasound promoted environmentally benign, highly efficient, and chemoselective N-tert-butyloxycarbonylation of amines by reusable sulfated polyborate
-
The sulfated polyborate catalyzed an efficient and chemoselective N-tert-butyloxycarbonylation of amines under ultrasonic irradiation is developed. A broad substrate scope has been demonstrated for N-Boc protection of various primary/secondary amines. It allows converting several aliphatic/aryl/heteroaryl amines, amino alcohol, aminoester, and chiral amines to their N-Boc-protected derivatives under solvent-free conditions with excellent yields. The protocol has several advantages such as easy catalyst, and product isolation, short reaction time, excellent yields, outstanding chemoselectivity, and catalyst recyclability, among others. This makes the process practicable, economical, and environmentally benign.
- Pise, Ashok S.,Ingale, Ajit P.,Dalvi, Navnath R.
-
supporting information
p. 3768 - 3780
(2021/10/26)
-
- Base-Mediated Generation of Ketenimines from Ynamides: [3+2] Annulation with Azaallyl Anions
-
Under basic conditions and heat, ynamides can serve as precursors to ketenimines, whose synthetic potential is often hampered by their difficulty of access. Herein, we report that they can undergo a [3+2] cycloaddition with 2-azaallyl anions, obtained from benzylimines under the same reaction conditions. This reaction between two highly reactive intermediates, both generated in situ from bench stable starting materials, gives access to various nitrogen-rich heterocycles. The reaction usually proceeds with excellent diastereoselectivity, in favor of the cis adduct. Deuteration experiments and DFT calculations helped rationalize the regio- and stereoselectivity of the process as well as the formation of side products. (Figure presented.).
- D'Hollander, Agathe C. A.,Romero, Eugénie,Vijayakumar, Kamsana,Le Houérou, Camille,Retailleau, Pascal,Dodd, Robert H.,Iorga, Bogdan I.,Cariou, Kevin
-
supporting information
p. 2903 - 2908
(2021/04/21)
-
- Mild deprotection of the: N-tert -butyloxycarbonyl (N -Boc) group using oxalyl chloride
-
We report a mild method for the selective deprotection of the N-Boc group from a structurally diverse set of compounds, encompassing aliphatic, aromatic, and heterocyclic substrates by using oxalyl chloride in methanol. The reactions take place under room temperature conditions for 1-4 h with yields up to 90percent. This mild procedure was applied to a hybrid, medicinally active compound FC1, which is a novel dual inhibitor of IDO1 and DNA Pol gamma. A broader mechanism involving the electrophilic character of oxalyl chloride is postulated for this deprotection strategy. This journal is
- Awuah, Samuel G.,George, Nathaniel,Ofori, Samuel,Parkin, Sean
-
p. 24017 - 24026
(2020/07/23)
-
- N-alkyl-hydroxybenzoyl anilide hydroxamates as dual inhibitors of HDAC and HSP90, downregulating IFN-γ induced PD-L1 expression
-
Novel dual inhibitors of histone deacetylase (HDAC) and heat-shock protein 90 (HSP90) are synthesized and evaluated. These compounds are endowed with potent HDAC and HSP90 inhibitory activities with IC50 values in nanomolar range with Compound 20 (HDAC IC50 = 194 nM; HSP90α IC50 = 153 nM) and compound 26 (HDAC IC50 = 360 nM; HSP90α IC50 = 77 nM) displaying most potent HDAC and HSP90α inhibitory activities. Both of these compounds induce HSP70 expression and down regulate HSP90 client proteins which play important roles in the regulation of survival and invasiveness in cancer cells. In addition, compounds 20 and 26 induce acetylation of α-tubulin and histone H3. Significantly, compounds 20 and 26 could effectively reduce programmed death-ligand 1 (PD-L1) expression in IFN-γ treated lung H1975 cells in a dose dependent manner. These findings suggest that dual inhibition of HDAC and HSP90 that can modulate immunosuppressive ability of tumor area may provide a better therapeutic strategy for cancer treatment in the future.
- Mehndiratta, Samir,Lin, Mei-Hsiang,Wu, Yi-Wen,Chen, Chun-Han,Wu, Tung-Yun,Chuang, Kuo-Hsiang,Chao, Min-Wu,Chen, Yi-Ying,Pan, Shiow-Lin,Chen, Mei-Chuan,Liou, Jing-Ping
-
-
- Discovery of a Novel Mycobacterial F-ATP Synthase Inhibitor and its Potency in Combination with Diarylquinolines
-
The F1FO-ATP synthase is required for growth and viability of Mycobacterium tuberculosis and is a validated clinical target. A mycobacterium-specific loop of the enzyme's rotary γ subunit plays a role in the coupling of ATP synthesis within the enzyme complex. We report the discovery of a novel antimycobacterial, termed GaMF1, that targets this γ subunit loop. Biochemical and NMR studies show that GaMF1 inhibits ATP synthase activity by binding to the loop. GaMF1 is bactericidal and is active against multidrug- as well as bedaquiline-resistant strains. Chemistry efforts on the scaffold revealed a dynamic structure activity relationship and delivered analogues with nanomolar potencies. Combining GaMF1 with bedaquiline or novel diarylquinoline analogues showed potentiation without inducing genotoxicity or phenotypic changes in a human embryonic stem cell reporter assay. These results suggest that GaMF1 presents an attractive lead for the discovery of a novel class of anti-tuberculosis F-ATP synthase inhibitors.
- Anbarasu, Sivaraj,Bates, Roderick W.,Dick, Thomas,Dr?ge, Peter,Grüber, Gerhard,Harikishore, Amaravadhi,Hotra, Adam,Kalia, Nitin Pal,Kalyanasundaram, Revathy,Lakshmanan, Umayal,Makhija, Harshyaa,Ng, Pearly Shuyi,Parthasarathy, Krupakar,Pethe, Kevin,Poulsen, Anders,Pradeep, Chaudhari Namrata,Ragunathan, Priya,Sae-Lao, Patcharaporn,Sarathy, Jickky Palmae,Saw, Wuan-Geok,Seankongsuk, Pattarakiat,Shin, Joon,Tan, Jocelyn Hui Ling
-
supporting information
p. 13295 - 13304
(2020/06/03)
-
- Organic/inorganic Fe3O4@MCM-41@Zr-piperazine: An impressive magnetite nanocatalyst for N-Tert-Butoxycarbonylation of amines
-
Fe3O4@MCM-41@Zirconium magnetic nanoparticles modified with piperazine (Fe3O4@MCM-41@Zr-piperazine), as a newly reported catalyst, shows excellent catalytic activity in N-tertbutoxycarbonylation of amines under the mild and solvent-free conditions. Accordingly, different derivatives of N-tert-butylcarbamates owning diverse aliphatic, aromatic and heteroaromatic amines were prepared efficiently. Good performance of this method for the majority of used complex or acidsensitive substrates and facile separation of this nanocatalyst due to its superparamagnetic nature from the reaction mixture via an external magnetic field for several times are the most important striking features of this protocol.
- Pourhasan-Kisomi, Reyhaneh,Shirini, Farhad,Golshekan, Mostafa
-
p. 3859 - 3870
(2019/05/08)
-
- Visible-Light-Mediated Nitration of Protected Anilines
-
The photocatalytic nitration of protected anilines proceeds with riboflavin tetraacetate as an organic photoredox catalyst. Sodium nitrite serves as the NO2 source in this visible-light-driven room temperature reaction. Various nitroanilines are obtained in moderate to good yields without the addition of acid or stoichiometric oxidation agents. The catalytic cycle is closed by aerial oxygen as the terminal oxidant.
- Düsel, Simon J. S.,K?nig, Burkhard
-
p. 2802 - 2807
(2018/03/09)
-
- Chemoselective: N-tert -butyloxycarbonylation of amines in glycerol
-
A catalyst-free, efficient and green protocol has been developed for the chemoselective N-Boc protection of amines by using glycerol as a solvent at room temperature. A variety of functionalized amines, such as aliphatic, aromatic as well as heteroaromatic were protected using the developed protocol. N-tert-Butyloxycarbonylation derivatives were formed without the formation of isocyanate, urea, N,N-di-t-Boc, or oxazolidinone as side products. The operational simplicity, cleaner reaction, rapid reaction convergence, functional group tolerance, excellent yield, high selectivity, catalyst-free feature and solvent recyclability are the distinct advantages of this protocol. Owing to these merits, this protocol is feasible, economical and environmentally benign.
- Ingale, Ajit P.,More, Vishal K.,Gangarde, Uddhav S.,Shinde, Sandeep V.
-
supporting information
p. 10142 - 10147
(2018/06/18)
-
- SMALL MOLECULE ACTIVATORS OF NICOTINAMIDE PHOSPHORIBOSYLTRANSFERASE (NAMPT) AND USES THEREOF
-
Provided herein are small molecule activators of Nicotinamide Phosphoribosyltransferase (NAMPT), compositions comprising the compounds, and methods of using the compounds and compositions.
- -
-
Paragraph 00694
(2018/08/03)
-
- HEAT SHOCK PROTEIN 90 INHIBITORS
-
Substituted aromatic compounds of formula (I) shown below: (formula I) The definition of each variable in formula (I) appears in the Specification. Also disclosed is a pharmaceutical composition containing one of the substituted aromatic compounds. Further disclosed is a method of using one of these compounds for treating a medical condition associated with HSP90.
- -
-
Page/Page column 30; 33; 35
(2018/10/19)
-
- [TPA][Pro] ionic liquid as efficient reaction medium for N-tert-Boc protection of amines
-
A facile and efficient N-tert-Boc protection of amines is described by the reaction of various primary, secondary, benzylic and aryl amines with di-tert-butyl dicarbonate in the ionic liquid [TPA][Pro] at room temperature. All the N-tert-butylcarbamates are afforded in excellent yields. A catalyst-free method was developed and the ionic liquid [TPA][Pro] can be recovered and reused for several times without loss of its activity.
- Vijaya Durga,Rambabu,Srinivasa Reddy,Hari Babu
-
p. 1313 - 1316
(2017/05/02)
-
- Copper nanoparticles catalyzed N-H functionalization: An efficient solvent-free N-tert-butyloxycarbonylation strategy
-
A chemoselective transformation of amines to their tert-butyloxycarbonyl (Boc) protected derivatives (NBoc) is described using Cu-NPs under solvent-free conditions. Simple method, rapid reaction rate, mild conditions, tolerance of a wide range of functional groups, excellent yield, ease recovery and high catalytic turnover are the salient features of this approach. tert-Butyloxycarbonylation of chiral amino acid esters and amino alcohols were performed without racemization.
- Deb, Barnali,Debnath, Sudipto,Deb, Anindita,Maiti, Dilip K.,Majumdar, Swapan
-
supporting information
p. 629 - 633
(2017/01/25)
-
- Palladium-Catalyzed Decarboxylative Synthesis of Arylamines
-
A novel approach has been developed for the synthesis of arylamines via the palladium-catalyzed intramolecular decarboxylative coupling (IDC) of aroyloxycarbamates, obtained in situ by reacting aryl carboxylic acids with hydroxycarbamates. The reaction offers facile access to structurally diverse arylamines with the site-specific formation of the C(sp2)-N bond under mild conditions.
- Dai, Qipu,Li, Peihe,Ma, Nuannuan,Hu, Changwen
-
supporting information
p. 5560 - 5563
(2016/11/17)
-
- Design and Synthesis of Janus Kinase 2 (JAK2) and Histone Deacetlyase (HDAC) Bispecific Inhibitors Based on Pacritinib and Evidence of Dual Pathway Inhibition in Hematological Cell Lines
-
Blockage of more than one oncoprotein or pathway is now a standard approach in modern cancer therapy. Multiple inhibition is typically achieved with two or more drugs. Herein, we describe a pharmacophore merging strategy combining the JAK2/FLT3 inhibitor pacritnib with the pan-HDAC inhibitor, vorinostat, to create bispecific single molecules with both JAK and HDAC targeted inhibition. A preferred ether hydroxamate, 51, inhibits JAK2 and HDAC6 with low nanomolar potency, is 50-fold selective for JAK2 in a panel of 97 kinases. Broad cellular antiproliferative potency is supported by demonstration of JAK-STAT and HDAC pathway blockade in several hematological cell lines, inhibition of colony formation in HEL cells, and analysis of apoptosis. This study provides new tool compounds for further exploration of dual JAK-HDAC pathway inhibiton achieved with a single molecule.
- Yang, Eugene Guorong,Mustafa, Nurulhuda,Tan, Eng Chong,Poulsen, Anders,Ramanujulu, Pondy Murugappan,Chng, Wee Joo,Yen, Jeffrey J. Y.,Dymock, Brian W.
-
supporting information
p. 8233 - 8262
(2016/10/03)
-
- HEPARAN SULFATE BIOSYNTHESIS INHIBITORS FOR THE TREATMENT OF DISEASES
-
Described herein are compounds of Formula I, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or conditions in need of inhibition of heparan sulfate biosynthesis.
- -
-
Paragraph 000795
(2016/05/02)
-
- Pd(II)/Ag(I)-Promoted One-Pot Synthesis of Cyclic Ureas from (Hetero)Aromatic Amines and Isocyanates
-
A simple and facile one-pot reaction has been developed to afford a diverse range of N,N′-disubstituted benzimidazolones and imidazopyridinones containing two differently substituted N atoms. A cooperative Pd(II)/Ag(I) system promotes the sequential addition/intramolecular C-H amidation reaction of (hetero)aromatic amines and isocyanates, leading to the formation of two C-N bonds. A mechanism involving radical intermediates generated by single-electron transfer (SET) in the presence of a Ag2CO3 oxidant and Pd(OAc)2 Lewis acid is proposed. This protocol offers an operationally easy, simple, and robust approach with the use of readily available starting materials, good functional group tolerance, and high efficiency.
- Youn, So Won,Kim, Yi Hyun
-
supporting information
p. 6140 - 6143
(2016/12/09)
-
- Aqueous MW eco-friendly protocol for amino group protection
-
In this paper a new catalyst-free and on-water method for protection of amines and amino acids with di-tert-butyl dicarbonate, 9-fluorenylmethoxycarbonyl chloride, acetyl chloride and tosyl chloride is presented. The protection can be realized in a few minutes under microwave-assistance. The reaction proved to be chemoselective in presence of ambident nucleophiles and water solution of di-tert-butyl carboxylic acid or chloride acid are the only wastes produced.
- Nardi,Cano, N. Herrera,Costanzo,Oliverio,Sindona,Procopio
-
p. 18751 - 18760
(2015/06/15)
-
- Preparation, characterization and application of succinimidinium hydrogensulfate ([H-Suc]HSO4) as an efficient ionic liquid catalyst for the N-Boc protection of amines
-
In this work, succinimidinium hydrogensulfate ([H-Suc]HSO4), as a novel Bronsted acidic ionic liquid is prepared and characterized by studying its FT-IR, 1H NMR, 13C NMR, mass and SEM. This reagent can be used as an efficient catalyst for the N-Boc protection of amines at room temperature and neat conditions. This new method consistently has the advantages of excellent yields and short reaction times. Further, this ionic liquid can be recovered and reused for several times. This journal is
- Shirini, Farhad,Jolodar, Omid Goli,Seddighi, Mohadeseh,Borujeni, Hojatollah Takbiri
-
p. 19790 - 19798
(2015/03/18)
-
- Direct Amidation of N-Boc- and N-Cbz-Protected Amines via Rhodium-Catalyzed Coupling of Arylboroxines and Carbamates
-
N-Boc- and N-Cbz-protected amines are directly converted into amides by a novel rhodium-catalyzed coupling of arylboroxines and carbamates, replacing the traditional two-step deprotection-condensation sequence. Both protected anilines and aliphatic amines are efficiently transformed into a wide variety of secondary benzamides, including sterically hindered and electron-deficient amides, as well as in the presence of acid-labile and reducible functional groups.
- Lim, Diane S. W.,Lew, Tedrick T. S.,Zhang, Yugen
-
supporting information
p. 6054 - 6057
(2016/01/09)
-
- General solvent-free highly selective N-tert-butyloxycarbonylation strategy using protic ionic liquid as an efficient catalyst
-
A simple, rapid and solvent-free protocol is described for the chemo-selective transformation of amines to tert-butyloxycarbonyl protected derivatives (NHBoc) using Boc2O and imidazolium trifluoroacetate protic ionic liquid (5-20 mol%). Unwanted side products such as isocyanate, urea or N,N-di-Boc were not detected. The scope of the protection strategy was successfully explored for substrate alcohols, phenols and thiol at elevated temperatures. Optically pure amino acids, amino acid esters and amino alcohols were efficiently converted to the corresponding N-Boc protected derivatives in excellent yields without racemization at the chiral center. The distinct advantages of this method are: operational simplicity, cleaner reaction, high selectivity, excellent yield, rapid reaction convergence, easy preparation and recyclability of the catalyst.
- Majumdar, Swapan,De, Jhinuk,Chakraborty, Ankita,Maiti, Dilip K.
-
p. 24544 - 24550
(2014/07/07)
-
- Iron(III)triflate as a highly efficient, recyclable and green catalyst for the N-Boc protection of amines
-
Iron (III) triflate was used as an efficient catalyst for N-t-butoxycarbonylation of amines with di-t-butyl dicarbonate under solvent-free conditions at room temperature. Various aliphatic, aromatic, heterocyclic amines and aminols were protected as their corresponding mono-carbamates in excellent yields and short reaction times. Only two of the 23 monocarbamates were new. No competitive side reactions such as isocyanate, urea, nor N,N-di-Boc formation were observed. The reported method is mild and has the advantages of low cost, chemoselectivity and, because no solvent is used and the catalyst can be recycled, it is classifiable as a green procedure.
- Feng, Chengliang,Chu, Ningning,Zhang, Shuguang,Cai, Jin,Chen, Junqing,Hu, Huayou,Ji, Min
-
p. 757 - 760
(2014/01/23)
-
- 1,3-Disulfonic acid imidazolium hydrogen sulfate as an efficient and reusable ionic liquid catalyst for the N-Boc protection of amines
-
1,3-Disulfonic acid imidazolium hydrogen sulfate is easily prepared and used as an efficient and recyclable ionic liquid for the N-Boc protection of amines at room temperature and neat conditions. This new method consistently has the advantages of excellent yields and short reaction times. Further, the catalyst can be reused and recovered for several times without loss of activity.
- Shirini, Farhad,Khaligh, Nader Ghaffari
-
p. 386 - 393
(2013/03/14)
-
- N-sulfonic acid poly(4-vinylpyridinium) chloride: An efficient and reusable solid acid catalyst in N-Boc protection of amines
-
N-sulfonic acid poly(4-vinylpyridinium) chloride is easily prepared by the reaction of poly(4-vinylpyridine) with neat chlorosulfonic acid. This reagent can be used as an efficient catalyst for the N-Boc protection of amines at room temperature and neat conditions. This new method consistently has the advantages of excellent yields and short reaction times. Further, the catalyst can be reused and recovered for several times.
- Shirini, Farhad,Khaligh, Nader Ghaffari,Jolodar, Omid Goli
-
p. 181 - 188
(2013/07/26)
-
- Nitration of tert-butyloxycarbonylated aniline and 1,3,5-triaminobenzene by acetyl nitrate
-
Acetyl nitrate was found to be an effective reagent for aromatic mono- and dinitration of Boc-protected aminobenzenes. The method was used in a new synthesis of 1,3,5-triamino-2,4-dinitrobenzene in two steps with 63% yield.
- Davis, Matthew C.,Groshens, Thomas J.
-
supporting information; experimental part
p. 4154 - 4155
(2012/08/28)
-
- Synthesis of (-)-oseltamivir by using a microreactor in the curtius rearrangement
-
A microflow reaction of the Curtius rearrangement by using trimethylsilyl azide as an azide source, followed by trapping of the generated isocyanate with a nucleophile was established, which is safe, inexpensive, and suitable for large-scale synthesis. By this flow reaction in the Curtius rearrangement and recrystallization of the late-stage acetamide intermediate the third-generation synthesis of (-)-Oseltamivir has been established, which is efficient, practical, and safe. A safe and efficient total synthesis of (-)-Oseltamivir has been developed by using the Curtius rearrangement with a microflow system, which avoids the isolation of a hazardous and potentially explosive intermediate. In addition, the product, possessing an acetamide group, was easily purified by recrystallization. Thus, this procedure can be scaled up as an industrial process.
- Ishikawa, Hayato,Bondzic, Bojan P.,Hayashi, Yujiro
-
experimental part
p. 6020 - 6031
(2011/12/15)
-
- FXA INHIBITORS WITH CYCLIC AMIDOXIME OR CYCLIC AMIDRAZONE AS P4 SUBUNIT, PROCESSES FOR THEIR PREPARATIONS, AND PHARMACEUTICAL COMPOSITIONS AND DERIVATIVES THEREOF
-
The present invention relates to novel oxazolidinone derivatives with cyclic amidoxime or cyclic amidrazone group, pharmaceutically acceptable salts thereof, methods for preparing the same and pharmaceutical compositions comprising the same. The oxazolidinone derivatives with cyclic amidoxime or cyclic amidrazone group or the pharmaceutically acceptable salts thereof can be effectively used for the treatment of thromboembolism and tumor as an anticoagulant based on the inhibition of factor Xa.
- -
-
-
- ZnO nanorods as an efficient and heterogeneous catalyst for N-Boc protection of amines and amine derivatives
-
An efficient ZnO nano catalyst, which was readily prepared from Zn(CH3CO2)2, 2H2O and PVP by a chemical solution approach has successfully catalyzed N-tertbutoxy carbonylation of amines. The ZnO nanorods were successful and gave promising results for highly active and chemoselective as well as easily recyclable catalyst for the NBoc protection reaction of a wide variety of amines. The catalyst could be easily recycled for five times without noticeable decrease in catalytic activity. The ZnO nanocatalyst was characterized with XRD and SEM.
- Nouria, Azita,Akbari, Jafar,Heydaric, Akbar,Nouri, Arezu
-
experimental part
p. 38 - 42
(2012/05/04)
-
- Pd-catalyzed amidation of aryl(Het) halides with tert-butyl carbamate
-
Pd-catalyzed cross-coupling reaction of tert-butyl carbamate with various aryl(Het) halides with Cs2CO3 as base in 1,4-dioxane as solvent was investigated, which resulted in the formation of the desired compounds in moderate to excellent yields.
- Qin, Lijin,Cui, Hongmeng,Zou, Dapeng,Li, Jingya,Wu, Yangjie,Zhu, Zhiwu,Wu, Yusheng
-
experimental part
p. 4445 - 4448
(2010/09/12)
-
- Protic ionic liquid [TMG][Ac] as an efficient, homogeneous and recyclable catalyst for Boc protection of amines
-
An efficient and practical protocol for the chemoselective N-Boc protection of various structurally different aryl, aliphatic and heterocyclic amines was carried out with (Boc)2O using protic 1, 1, 3, 3-tetra-methylguanidinium acetate (10 mol%) as recyclable catalyst under solvent free condition at ambient temperature. No competitive side reactions (isocyanate, urea and N, N-di-Boc) were observed. α-Amino alcohols afforded the N-Boc-derivative without oxazolidinone formation.
- Akbari, Jafar,Heydari, Akbar,Ma'mani, Leila,Hassan Hosseini, Seyed
-
experimental part
p. 544 - 547
(2010/11/05)
-
- FXA INHIBITORS WITH CYCLIC AMIDOXIME OR CYCLIC AMIDRAZONE AS P4 SUBUNIT, PROCESSES FOR THEIR PREPARATIONS, AND PHARMACEUTICAL COMPOSITIONS AND DERIVATIVES THEREOF
-
The present invention relates to novel oxazolidinone derivatives with cyclic amidoxime or cyclic amidrazone group, pharmaceutically acceptable salts thereof, methods for preparing the same and pharmaceutical compositions comprising the same. The oxazolidinone derivatives with cyclic amidoxime or cyclic amidrazone group or the pharmaceutically acceptable salts thereof can be effectively used for the treatment of thromboembolism and tumor as an anticoagulant based on the inhibition of factor Xa.
- -
-
Page/Page column 19-20
(2010/04/03)
-
- 1-[4-(N-Benzylamino)phenyl]-3-phenylurea derivatives as a new class of hypoxia-inducible factor-1α inhibitors
-
A series of 1-[4-(N-benzylamino)phenyl]-3-phenylurea derivatives 2a-r were synthesized as HIF-1α inhibitors. Among the compounds synthesized, compound 2k was found to be a potent inhibitor against HIF-1α accumulation under hypoxic condition and inhibited the hypoxia-induced HIF-1 transcriptional activity in HEK293 cells (IC50 = 7.2 μM). Furthermore, compound 2k suppressed the hypoxia-induced secretion of VEGF in HeLa cells (IC50 = 15 μM).
- Uno, Masaharu,Ban, Hyun Seung,Nakamura, Hiroyuki
-
scheme or table
p. 3166 - 3169
(2010/03/03)
-
- FXA INHIBITORS WITH CYCLIC AMIDINES AS P4 SUBUNIT, PROCESSES FOR THEIR PREPARATIONS, AND PHARMACEUTICAL COMPOSITIONS AND DERIVATIVES THEREOF
-
The present invention relates to novel oxazolidinone derivatives with cyclic araidines, and prodrugs, hydrates, solvates, isomers and pharmaceutically acceptable salts thereof, and processes for preparing the same, and pharmaceutical compositions comprising the same. The oxazolidinone derivatives with cyclic amidines, and prodrugs, hydrates, solvates, isomers and pharmaceutically acceptable salts thereof can be usefully employed as an anticoagulant for treating thromboembolism and tumors via inhibition of coagulation factor Xa.
- -
-
-
- Copper-catalyzed coupling of hydroxylamines with aryl iodides
-
An efficient method for the copper-catalyzed N-arylation of hydroxylamines with aryl iodides is described. A variety of N- and O-functionalized hydroxylamines were transformed in good to excellent yield with a broad range of aryl coupling partners. Methods for the selective deprotection of either the N- or O-substituents for further functionalization are also described.
- Jones, Kerri L.,Porzelle, Achim,Hall, Adrian,Woodrow, Michael D.,Tomkinson, Nicholas C. O.
-
supporting information; experimental part
p. 797 - 800
(2009/04/06)
-
- De novo Design and synthesis of N-benzylanilines as new candidates for VEGFR tyrosine kinase inhibitors
-
N-Benzylanilines were designed and synthesized as vascular endothelial growth factor (VEGF)-2 inhibitors using de novo drug design systems based on the X-ray structure of VEGFR-2 kinase domain. Among compounds synthesized, compound 3 showed the most potent inhibitory activity toward VEGFR-2 (KDR) tyrosine kinase and its IC50 value was 0.57 μM.
- Uno, Masaharu,Ban, Hyun Seung,Nabeyama, Wataru,Nakamura, Hiroyuki
-
scheme or table
p. 979 - 981
(2009/02/05)
-
- An efficient and chemoselective Br?nsted acidic ionic liquid-catalyzed N-Boc protection of amines
-
The first report of a Br?nsted acidic ionic liquid, 1-methylimidazolium tetrafluoroborate [(HMIm)BF4], catalyzed efficient and chemoselective N-Boc protection of various amines using (Boc)2O is presented. Optically pure amino alcohols and amino acid esters were converted efficiently to their corresponding optically pure N-Boc derivatives. The reported method is mild, solvent-free and has the advantages of both homogeneous and heterogeneous catalysis with high product yields, selectivity and ease of product separation.
- Sunitha, Sadula,Kanjilal, Sanjit,Reddy, P. Srinivasa,Prasad, Rachapudi B.N.
-
p. 2527 - 2532
(2008/09/19)
-
- Efficient, solventless N-Boc protection of amines carried out at room temperature using sulfamic acid as recyclable catalyst
-
A simple, rapid, and efficient protocol for the chemoselective N-Boc protection of amines using sulfamic acid as catalyst is described. N-Boc protection of various structurally diverse aliphatic, aromatic, alicyclic, and heterocyclic amines (1°, 2°, 3°) was carried out with (Boc)2O using sulfamic acid as catalyst (5 mol %) at room temperature under solventless conditions. The advantages of this method are simplicity, shorter reaction times (1-15 min), a cost-effective catalyst, and excellent isolated yields (90-100%); it is also environmentally benign. Moreover, the combined use of ultrasound and sulfamic acid achieves a synergic effect that is especially marked in the N-Boc protection of deactivated (sterically hindered and electron-deficient) amines. The catalyst possesses distinct advantages: ease of handling, cleaner reactions, high activity, and excellent chemoselectivity.
- Upadhyaya, Dharita J.,Barge, Alessandro,Stefania, Rachele,Cravotto, Giancarlo
-
p. 8318 - 8322
(2008/04/13)
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- Environmentally benign N-Boc protection under solvent- and catalyst-free conditions
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A practical and highly efficient method for the protection of amines to their corresponding N-Boc derivatives is reported. In the absence of any solvent and catalyst, the present strategy works well for a series of electron-deficient and electron-rich aromatic amines as well as some sterically hindered substrates. Georg Thieme Verlag Stuttgart.
- Jia, Xueshun,Huang, Qing,Li, Jian,Li, Shaoyu,Yang, Qiushi
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p. 806 - 808
(2007/12/26)
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- N-tert-Butoxycarbonylation of amines using H3PW12O40 as an efficient heterogeneous and recyclable catalyst
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The commercially available heteropoly acid H3PW12O40 (0.5 mol %) is a very efficient and environmentally benign catalyst for N-tert-butoxycarbonylation of amines (primary, secondary) with di-tert-butyl dicarbonate at room temperature in short reaction times (10 min). No competitive side products such as isocyanates, ureas, N,N-di-tert-butoxycarbonyls, O-Boc and oxazolidinones were observed. Chiral α-amino alcohols and esters afforded the corresponding N-Boc derivatives chemoselectively in excellent yields.
- Heydari, Akbar,Shiroodi, Roohollah Kazem,Hamadi, Hossein,Esfandyari, Maryam,Pourayoubi, Mehrdad
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p. 5865 - 5868
(2008/02/09)
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- A novel tert-butoxycarbonylation reagent: 1-tert-butoxy-2-tert-butoxycarbonyl-1,2-dihydroisoquinoline (BBDI)
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The use of 1-tert-butoxy-2-tert-butoxycarbonyl-1,2-dihydroisoquinoline (BBDI) as a tert-butoxycarbonylation reagent for acidic proton-containing substrates such as phenols, aromatic and aliphatic amines hydrochlorides, and aromatic carboxylic acids in the absence of a base is described. The reactions proceed chemoselectively in high yield under mild conditions.
- Saito, Yukako,Ouchi, Hidekazu,Takahata, Hiroki
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p. 11599 - 11607
(2007/10/03)
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- Facile N-tert-butoxycarbonylation of amines using La(NO3)3·6H2O as a mild and efficient catalyst under solvent-free conditions
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Facile N-tert-butoxycarbonylation of amines is described by the treatment of various primary, secondary, benzylic and aryl amines with di-tert-butyl dicarbonate in the presence of catalytic amounts of La(NO3)3·6H2O under solvent-free conditions at room temperature to afford N-tert-butylcarbamates in excellent yields.
- Suryakiran,Prabhakar,Reddy, T. Srikanth,Rajesh,Venkateswarlu
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p. 8039 - 8042
(2007/10/03)
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- Molecular iodine-catalyzed facile procedure for N-Boc protection of amines
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An efficient and practical protocol for the protection of various structurally and electronically divergent aryl and aliphatic amines using (Boc)2O in the presence of a catalytic amount of molecular iodine (10 mol%) under solvent-free conditions at ambient temperature is presented.
- Varala, Ravi,Nuvula, Sreelatha,Adapa, Srinivas R.
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p. 8283 - 8286
(2007/10/03)
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- Copper(II) tetrafluoroborate as a novel and highly efficient catalyst for N-tert-butoxycarbonylation of amines under solvent-free conditions at room temperature
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Commercially available copper(II) tetrafluoroborate hydrate was found to be a highly efficient catalyst for chemoselective N-tert-butoxycarbonylation of amines with di-tert-butyl dicarbonate under solvent-free conditions and at room temperature. Various aromatic amines were protected as their N-tert-butyl carbamates in high yields and in short times. No competitive side reactions such as isocyanate, urea, and N,N-di-t-Boc formation was observed. Chemoselective N-tert-butoxycarbonylation was achieved with substrates bearing OH and SH groups. Chiral α-amino acid esters afforded the corresponding N-t-Boc derivatives in excellent yields.
- Chankeshwara, Sunay V.,Chakraborti, Asit K.
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p. 1087 - 1091
(2007/10/03)
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- A rate enhancement of tert-butoxycarbonylation of aromatic amines with Boc2O in alcoholic solvents
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A rate enhancement of tert-butoxycarbonylation of aromatic amines by Boc2O in alcohols compared to aprotic solvents was demonstrated. Kinetic analysis by NMR suggested that the reaction in CD3OD was faster than in CDCl3 by a factor of 70. Reactions between Boc2O and various aliphatic and aromatic amines in ethanol provided the N-Boc derivatives in good to excellent yields in short reaction times.
- Vilaivan, Tirayut
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p. 6739 - 6742
(2007/10/03)
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- Arylisothiocyanato selective androgen receptor modulators (SARMs) for prostate cancer
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A new series of androgen receptor targeted agents (ARTA) was prepared and tested in androgen-dependent and -independent prostate cancer cell lines. These agents were bicalutamide analogs with isothiocyanato substituted B-rings. Also, the linker sulfone of R-bicalutamide was maintained or replaced with several alternative linkages including ether, amine, N-methylamine, thioether, and methylene (in this case the product was a racemic mixture) functional groups at the X-position. To expand the structure-activity relationship (SAR) of these arylisothiocyanato AR ligands, B-ring halogenated arylisothiocyanato ligands were also prepared and tested. The arylisothiocyanato AR ligands showed strong binding affinities to AR ranging from 0.6 to 54 nM. Among them, thioether and ether linkages demonstrated high binding affinities (0.6 and 4.6 nM, respectively) and selective cell growth inhibition (approximately 3- to 6-fold) for LNCaP, an androgen-dependent prostate cancer cell line, when compared to the androgen independent prostate cell lines (DU145, PC-3, and PPC-1) and a bladder cell line (TSU-Pr1). However, the ligands were inactive (IC50>100 mM) in a normal monkey kidney cell line (CV-1) that was used as the control for non-specific toxicity.
- Hwang, Dong Jin,Yang, Jun,Xu, Huiping,Rakov, Igor M.,Mohler, Michael L.,Dalton, James T.,Miller, Duane D.
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p. 6525 - 6538
(2007/10/03)
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- Lithium perchlorate-catalyzed Boc protection of amines and amine derivatives
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A new mild and chemoselective method for mono-N-protection of amines and amine derivatives as tert-butoxycarbonyl derivatives is reported. The reaction proceeds with lithium perchlorate (20 mol %) and pyrocarbonates, and shows general applicability. The catalytic action of LiClO4 is specific for the activation of Boc2O, thus acid-sensitive functionalities of the starting materials remain unchanged in the protection process. This procedure works well for sterically hindered primary amine as well as electron-deficient primary arylamines, primary and secondary amino alcohols, α-amino acid esters, hydroxylamines, hydrazines and sulfonamides.
- Heydari, Akbar,Hosseini, Seyed Esmaeil
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p. 1929 - 1932
(2007/10/03)
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- A Lewis acid-mediated protocol for the protection of aryl amines as their Boc-derivatives
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A new protocol of protection of poorly reactive aryl amines and functionalized amines with Boc2O in the presence of Zn(ClO 4)2·6H2O as the catalyst is reported. The catalytic action of Zn(ClO4)2·6H2O is specific for the activation of the pyrocarbonates, thus acid sensitive functionalities and stereochemical configurations of the starting materials remain unaltered in the protection process.
- Bartoli, Giuseppe,Bosco, Marcella,Locatelli, Manuela,Marcantoni, Enrico,Massaccesi, Massimo,Melchiorre, Paolo,Sambri, Letizia
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p. 1794 - 1798
(2007/10/03)
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- Process for producing N-acylnitroaniline derivative
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A process of reacting a nitroaniline compound of formula (2); with acid anhydride or acid chloride is carried out in the presence of an alkali metal compound or an alkaline earth metal compound to produce acylnitroaniline derivative. The process further includes the step of reacting the resulting product with a compound of formula (5);R2-Y to produce an N-acylnitroaniline derivative of formula (1);
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- Ag+ mediated deaminations of N-Boc aryl hydrazines for the efficient synthesis of N-Boc aryl amines
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N-Boc-aryl hydrazines were converted into N-Boc-aryl amines under the action of Ag+. Its mild reaction conditions tolerate the presence of a variety of functional groups.
- Lee, Kang-Sang,Lim, Young-Kwan,Cho, Cheon-Gyu
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p. 7463 - 7464
(2007/10/03)
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