- N-pyridinylbenzamides: an isosteric approach towards new antimycobacterial compounds
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A series of N-pyridinylbenzamides was designed and prepared to investigate the influence of isosterism and positional isomerism on antimycobacterial activity. Comparison to previously published isosteric N-pyrazinylbenzamides was made as an attempt to draw structure–activity relationships in such type of compounds. In total, we prepared 44 different compounds, out of which fourteen had minimum inhibitory concentration (MIC) values against Mycobacterium tuberculosis H37Ra below 31.25?μg/ml, most promising being N-(5-chloropyridin-2-yl)-3-(trifluoromethyl)benzamide (23) and N-(6-chloropyridin-2-yl)-3-(trifluoromethyl)benzamide (24) with MIC?=?7.81?μg/ml (26?μm). Five compounds showed broad-spectrum antimycobacterial activity against M. tuberculosis H37Ra, M. smegmatis and M. aurum. N-(pyridin-2-yl)benzamides were generally more active than N-(pyridin-3-yl)benzamides, indicating that N-1 in the parental structure of N-pyrazinylbenzamides might be more important for antimycobacterial activity than N-4. Marginal antibacterial and antifungal activity was observed for title compounds. The hepatotoxicity of title compounds was assessed in vitro on hepatocellular carcinoma cell line HepG2, and they may be considered non-toxic (22 compounds with IC50 over 200?μm).
- Nawrot, Daria,Suchánková, Eli?ka,Jan?ourek, Ond?ej,Kone?ná, Klára,Bárta, Pavel,Dole?al, Martin,Zitko, Jan
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p. 686 - 700
(2020/11/30)
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- Co2(CO)8as a Solid CO (g) Source for the Amino Carbonylation of (Hetero)aryl Halides with Highly Deactivated (Hetero)arylamines
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Carbonylation of (hetero)aryl iodides/bromides with highly deactivated 2-aminopyridines using Pd-Co(CO)4 bimetallic catalysis is accomplished. The use of Co2(CO)8 as a solid CO(g) source enhanced reaction rates observed when compared to CO(g), and excellent yields highlight the versatility of the developed protocol. A wide range of electronically and sterically demanding heterocyclic amines and (hetero)aryl iodides/bromides employed for this study resulted in excellent yields of amino carbonylated products. The developed methodology was further extended to synthesize Trypanosome brucie and luciferase inhibitors.
- Cheruku, Srinivas,Sajith, Ayyiliath M.,Narayana, Yatheesh,Shetty, Poornima,Nagarakere, Sandhya C.,Sagar, Kunigal S,Manikyanally, Kumara N.,Rangappa, Kanchugarkoppal Subbegowda,Mantelingu, Kempegowda
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p. 5530 - 5537
(2021/05/07)
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- Direct Transformation of Alkylarenes into N-(Pyridine-2-yl)amides by C(sp3)–C(sp3) Bond Cleavage
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C(sp3)–H bond functionalization and C(sp3)–C(sp3) bond cleavage are very challenging transformations in chemistry. Herein, we report a mild and green methodology for the construction of N-(pyridine-2-yl)amides via tandem C(sp3)–H activation/C–C bond cleavage of alkylarenes. Various N-heterocyclic amides were directly synthesized from alkylarenes in water in moderate to good yields.
- Zhou, Haipin,Liu, Yanpeng,Xia, Haidong,Xu, Jinyi,Wang, Tingfang,Xu, Shengtao
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p. 6468 - 6473
(2020/10/02)
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- Exploring Homogeneous Conditions for Mild Buchwald-Hartwig Amination in Batch and Flow
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Cross-couplings are among the most frequently used reactions in complex molecule synthesis. However, the requirement of stoichiometric base can cause challenges. Harsh, insoluble inorganic bases can lead to poor tolerance of sensitive functional groups, scale-up issues, and difficult adaptation to continuous flow platforms. Herein, we describe the use of high throughput experimentation to identify a number of conditions that enable Buchwald-Hartwig reactions to be carried out using readily available ligands (e.g., XantPhos) with DBU as a soluble, functional-group-tolerant, homogeneous base. Application of this system to diverse aminations in batch and flow are demonstrated, as is the translation of this technique to performing continuous Mizoroki-Heck and Sonogashira coupling reactions.
- Kashani, Saeed K.,Jessiman, Jacob E.,Newman, Stephen G.
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supporting information
p. 1948 - 1954
(2020/03/13)
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- Singlet oxygen mediated dual C-C and C-N bond cleavage in visible light
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A tandem cleavage of carbon-carbon and carbon-nitrogen bonds in imidazo[1,2-a]pyridines and imidazo[1,2-a]quinolines is reported in the presence of eosin Y and visible light. The ring opening occurs under ambient conditions through singlet oxygen insertio
- Jain, Nidhi,Kumar, Sharvan,Ritu,Sharma, Charu
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p. 2921 - 2928
(2020/04/28)
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- Chemodivergent synthesis of: N -(pyridin-2-yl)amides and 3-bromoimidazo[1,2- a] pyridines from α-bromoketones and 2-aminopyridines
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N-(Pyridin-2-yl)amides and 3-bromoimidazo[1,2-a]pyridines were synthesized respectively from α-bromoketones and 2-aminopyridine under different reaction conditions. N-(Pyridin-2-yl)amides were formed in toluene via C-C bond cleavage promoted by I2/s
- Liu, Yanpeng,Lu, Lixue,Zhou, Haipin,Xu, Feijie,Ma, Cong,Huang, Zhangjian,Xu, Jinyi,Xu, Shengtao
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p. 34671 - 34676
(2019/11/13)
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- Iron(II)-Based Metalloradical Activation: Switch from Traditional Click Chemistry to Denitrogenative Annulation
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A unique concept for the intermolecular denitrogenative annulation of 1,2,3,4-tetrazoles and alkynes was discovered by using a catalytic amount of Fe(TPP)Cl and Zn dust. The reaction precludes the traditional, more favored click reaction between an organic azide and alkynes, and instead proceeds by an unprecedented metalloradical activation. The method is anticipated to advance access to the construction of important basic nitrogen heterocycles, which will in turn enable discoveries of new drug candidates.
- Roy, Satyajit,Khatua, Hillol,Das, Sandip Kumar,Chattopadhyay, Buddhadeb
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p. 11439 - 11443
(2019/07/17)
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- Copper Catalyzed Oxidative C-C Bond Cleavage of 1,2-Diketones: A Divergent Approach to 1,8-Naphthalimides, Biphenyl-2,2′-dicarboxamides, and N-Heterocyclic Amides
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We report here a simple and efficient copper catalyzed oxidative C-C bond cleavage of stable aromatic cyclic-fused and acyclic 1,2-diketones to deliver amides and imides in high yields. This newly developed protocol provides an excellent tool to transform structurally different 1,2-diketones into different products under the same reaction conditions. The key synthetic features of this methodology are the formation of 1,8-naphthalimides and biphenyl-2,2′-dicarboxamide motifs in high yields. The fluorescent studies of 1,8-naphthalimide derivatives were also carried out in order to show the potential application of these scaffolds.
- Sakhare, Priyanka R.,Subramanian, Parthasarathi,Kaliappan, Krishna P.
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p. 2112 - 2125
(2019/02/14)
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- Singlet oxygen mediated one pot synthesis of N-pyridinylamides via oxidative amidation of aryl alkyl ketones
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An environmental friendly, efficient protocol has been realized for the synthesis of N-pyridinylamides via copper catalyzed oxidative amidation of aryl alkyl ketones with 2-aminopyridines. This one pot protocol involves chemo selective cleavage of C (O)–C bond in the presence of singlet oxygen. The reaction conditions are simple, tolerates wide range of substrates and the products were formed in good to excellent yields. This method offers a moderate improvement over the earlier successful attempts in generating N-pyridinylamides.
- Sofi, Firdoos Ahmad,Sharma, Rohit,Kavyasree,Salim, Sumi Aisha,Wanjari, Pravin J.,Bharatam, Prasad V.
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supporting information
(2019/09/10)
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- Ruthenium-Catalyzed Reductive Arylation of N-(2-Pyridinyl)amides with Isopropanol and Arylboronate Esters
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A new three-component reductive arylation of amides with stable reactants (iPrOH and arylboronate esters), making use of a 2-pyridinyl (Py) directing group, is described. The N-Py-amide substrates are readily prepared from carboxylic acids and PyNH2, and the resulting N-Py-1-arylalkanamine reaction products are easily transformed into the corresponding chlorides by substitution of the HN-Py group with HCl. The 1-aryl-1-chloroalkane products allow substitution and cross-coupling reactions. Therefore, a general protocol for the transformation of carboxylic acids into a variety of functionalities is obtained. The Py-NH2 by-product can be recycled.
- Ronson, Thomas O.,Renders, Evelien,Van Steijvoort, Ben F.,Wang, Xubin,Wybon, Clarence C. D.,Prokopcová, Hana,Meerpoel, Lieven,Maes, Bert U. W.
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supporting information
p. 482 - 487
(2019/01/04)
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- Metal-Free Synthesis of N-(Pyridine-2-yl)amides from Ketones via Selective Oxidative Cleavage of C(O)-C(Alkyl) Bond in Water
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The TBHP/TBAI-mediated synthesis of N-(pyridine-2-yl)amides in water from ketones and 2-aminopyridine via direct oxidative C-C bond cleavage has been developed. A series of ketones, including more challenging inactive aromatic ketones substituted with div
- Liu, Yanpeng,Sun, Honghao,Huang, Zhangjian,Ma, Cong,Lin, Aijun,Yao, Hequan,Xu, Jinyi,Xu, Shengtao
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p. 14307 - 14313
(2019/01/03)
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- Copper(II)-mediated, carbon degradation-based amidation of phenylacetic acids toward N -substituted benzamides
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The unprecedented synthesis of N-aryl substituted benzamides via the assembly of primary amines and phenylacetic acids has been developed in the presence of copper(ii) acetate. This tandem transformation involving carbon-carbon bond cleavage provides a complementary tool with particular application in the synthesis of secondary benzamides.
- Deng, Leiling,Huang, Bin,Liu, Yunyun
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supporting information
p. 1552 - 1556
(2018/03/08)
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- Ce(III)-catalyzed highly efficient synthesis of pyridyl benzamides from aminopyridines and nitroolefins without external oxidants
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An efficient synthesis of a variety of pyridyl benzamides from 2-aminopyridines and nitroolefins is described. This rare-earth-metal-catalyzed reaction provides the corresponding products with broad substrate scope in moderate to excellent yields, in the absence of additives and external oxidants. Water is used as the source of the carbonyl oxygen atom in pyridyl benzamides. Furthermore, 2-substituted oxazolo[4,5-b]pyridines are formed in good yields under the standard conditions when 2-aminopyridin-3-ols are used as the substrates.
- Chen, Zhengwang,Wen, Xiaowei,Qian, Yiping,Liang, Pei,Liu, Botao,Ye, Min
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supporting information
p. 1247 - 1251
(2018/03/06)
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- Copper(i)-catalysed oxidative C-N coupling of 2-aminopyridine with terminal alkynes featuring a CC bond cleavage promoted by visible light
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Facile visible-light promoted copper-catalyzed aerobic oxidative C-N coupling between 2-aminopyridine and terminal alkynes at room temperature via CC triple bond cleavage is described. This reaction allows direct synthesis of biologically important pyridy
- Ragupathi, Ayyakkannu,Sagadevan, Arunachalam,Lin, Chun-Cheng,Hwu, Jih-Ru,Hwang, Kuo Chu
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supporting information
p. 11756 - 11759
(2016/10/07)
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- Metal-free TBHP-mediated oxidative ring openings of 2-arylimidazopyridines via regioselective cleavage of C-C and C-N bonds
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A highly regioselective TBHP-mediated ring opening of imidazopyridines via cleavage of C-C and C-N bonds has been achieved for the first time to afford N-(pyridin-2-yl)benzamides. Preliminary mechanistic investigations revealed that the present metal-free
- Yan, Kelu,Yang, Daoshan,Wei, Wei,Li, Guoqing,Sun, Mingyang,Zhang, Qingyun,Tian, Laijin,Wang, Hua
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p. 100102 - 100105
(2015/12/05)
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- ORGANIC MOLECULES FOR TERAHERTZ TAGGING APPLICATIONS
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The present invention discloses substituted heterocyclic compounds and /or aromatic compounds containing amide and/or urea groups exhibiting resonance in the range of 0.1- 10 THz. The invention also discloses binary molecular complexes based on the substituted heterocyclic compounds and/or aromatic compounds containing amide and/or urea groups of the present invention. The compounds and binary molecular complexes of the present invention have varying molecular mass and hydrogen bond strengths demonstrating several resonances below 10 THz. The compounds and binary molecular complexes of the present invention are customizable for various applications, such as authentication of a product.
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Page/Page column 15-16
(2015/07/23)
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- A one-pot copper catalyzed biomimetic route to n -heterocyclic amides from methyl ketones via oxidative c-c bond cleavage
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A direct one-pot Cu-catalyzed biomimetic oxidation of methyl ketones to pharmaceutically important N-heterocyclic amides is reported. The scope of the method is broad, scalable, and mild, and the reaction is tolerant with various acid, base sensitive functionalities with multiple heteroatoms and aryl halides. The extensive mechanistic studies suggest that this reaction follows the Luciferin-Luciferase-like pathway.
- Subramanian, Parthasarathi,Indu, Satrajit,Kaliappan, Krishna P.
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supporting information
p. 6212 - 6215
(2015/01/09)
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- Copper-catalysed amidation of 2-chloro-pyridines
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The simple and inexpensive N,N-dimethylcyclohexane-1,2-diamine/CuI catalytic system provides a versatile, easy and efficient access to an array of N-(2-pyridin-2-yl)-amides from 2-chloro-pyridine derivatives. The Royal Society of Chemistry 2013.
- Nicolas, Lionel,Angibaud, Patrick,Stansfield, Ian,Meerpoel, Lieven,Reymond, Sebastien,Cossy, Janine
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p. 18787 - 18790
(2013/10/22)
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- COMPOUNDS THAT EXPAND HEMATOPOIETIC STEM CELLS
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The present invention relates to compounds and compositions for expanding the number of CD34+ cells for transplantation. The invention further relates to a cell population comprising expanded hematopoietic stem cells (HSCs) and its use in autologous or allogeneic transplantation for the treatment of patients with inherited immunodeficient and autoimmune diseases and diverse hematopoietic disorders to reconstitute the hematopoietic cell lineages and immune system defense.
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Page/Page column 33; 36
(2012/08/08)
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- Palladium-catalysed multicomponent aminocarbonylation of aryl or heteroaryl halides with Mo(CO)6i and aryl- or heteroarylamines using conventional heating
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Di(hetero)arylamides have been synthesized in short reaction times by palladium-catalysed multicomponent aminocarbonylation of either electron-deficient or electron-rich heteroaryl halides and p-iodoanisole with, several, arylamines bearing either electro
- Begouin, Agathe,Queiroz, Maria-Joao R. P.
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experimental part
p. 2820 - 2827
(2009/09/06)
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- Ru-catalyzed hydroamidation of alkenes and cooperative aminocarboxylation procedure with chelating formamide
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(Matrix presented) A strategy of chelation-assisted activation of formamide was employed to achieve hydroamidation of alkenes to generate one-carbon-elongated amides in moderate to good selectivity and yields. Also reported is the two-metal-catalyzed cooperative aminocarboxylation of aryl iodides, in which Ru is presumed to catalyze decarbonylation of formamide to release carbon monoxide and amine for the subsequent Pd-catalyzed aminocarboxylation routes, thus enabling the net transformation to be performed in the absence of external CO pressure.
- Ko, Sangwon,Han, Hoon,Chang, Sukbok
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p. 2687 - 2690
(2007/10/03)
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- Formation and Pyrolysis of 1-(2'-Pyridyl)-5-aryltetrazoles
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A number of 1-(2'-pyridyl)-5-aryltetrazoles (Va-k) have been obtained by the reaction of 2-aroylamidopyridines (III) with phosphorus pentachloride and azidolysis of the resulting imidoyl chlorides.The products obtained on pyrolysis of 1-(2'-pyridyl)-5-ary
- Rao, P. Jayaprasad,Reddy, K. Kondal
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p. 117 - 120
(2007/10/02)
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