- Synthesis of All-Carbon Quaternary Centers by Palladium-Catalyzed Olefin Dicarbofunctionalization
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The redox-neutral dicarbofunctionalization of tri- and tetrasubstituted olefins to form a variety of (hetero)cyclic compounds under photoinduced palladium catalysis is described. This cascade reaction process was used to couple styrenes or acryl amides with a broad range of highly decorated olefins tethered to aryl or alkyl bromides (>50 examples). This procedure enables one or two contiguous all-carbon quaternary centers to be formed in a single step. The products could be readily diversified and applied in the synthesis of a bioactive oxindole analogue.
- Koy, Maximilian,Bellotti, Peter,Katzenburg, Felix,Daniliuc, Constantin G.,Glorius, Frank
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supporting information
p. 2375 - 2379
(2020/01/24)
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- Synthesis, molecular docking, α-glucosidase inhibition, and antioxidant activity studies of novel benzimidazole derivatives
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A novel series of N-methyl/benzyl-substituted benzimidazolyl-linked para-substituted benzyl-based compounds containing 2,4-thiazolidinediones, dimethyl malonate (DMM), and diethyl malonate (DEM) 17–27 were designed, docked, synthesized, and evaluated for their antidiabetic activity studies. Structures of all the synthesized compounds were confirmed through 1H NMR, 13C NMR, FTIR, and mass spectrometry. Four targeted compounds (17–18 and 22–23) showed good inhibitory potential in the range of 4.10 ± 0.01 to 9.12 ± 0.06 μM. Furthermore, synthesized compounds 17–27 were evaluated for their antioxidant potential and compared with standard ascorbic acid and results showed that compound 18 (EC50 = 0.176 ± 0.002 mM) being the most active. Compounds 17–18 and 22–23 exhibited prominent antidiabetic as well as antioxidant activity. Compound 18 was considered a promising candidate for this series. The designed molecules were docked into α-glucosidase protein (PDB Code. 3TOP) to develop a correlation with the α-glucosidase inhibition studies and were also additionally docked into PPARγ proteins (PDB ID: 2PRG) with rosiglitazone (standard drug) to study their PPARγ binding affinity in comparison with rosiglitazone and to classify these compounds for their PPARγ agonistic behavior.
- Singh, Gagandeep,Singh, Amanjot,Singh, Varinder,Verma, Raman K.,Tomar, Jyoti,Mall, Rajiv
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p. 1846 - 1866
(2020/08/03)
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- Effect of acetate and nitrate anions on the molecular structure of 3-(hydroxyimino)-2-butanone-2-(1H-benzimidazol-2-yl)hydrazone
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A novel Schiff base ligand 3-(hydroxyimino)-2-butanone-2-(1H-benzimidazol-2-yl)hydrazone has been synthesized by the condensation reaction of 2-Hydrazinobenzimidazole with diacetyl monoxime in presence of acetic acid catalyst. The ligand has crystallized as its acetate salt, due to the charge-assisted hydrogen bonding between protonated benzimidazole ring and acetate anion. Efforts to synthesize the zinc(II) complex of the title compound, has resulted in the formation of a nitrate salt of the ligand, instead of coordination complex of zinc(II). Acetate salt has crystallized in monoclinic P 21/n, while the nitrate salt has crystallized in a triclinic crystal system with P -1 space group. Hirshfeld surface analysis is presented for both of the crystal structures. Structures of synthesized molecules are even computationally optimized using DFT. A comparative structural approach between the synthesized molecules and DFT optimized structure of bare ligand without any counterions is analyzed in terms of bond parameters. Hydrogen bonding is explained keeping the anions as the central dogma. Mass fragmentation pattern of the organic molecule and comparative account of IR, 1H and 13C NMR chemical shifts are also presented. Compounds are screened for their antibacterial and antifungal potencies against few pathogenic microorganisms. The organic motif is found be an excellent antifungal agent.
- Kamat, Vinayak,Naik, Krishna,Revankar, Vidyanand K.
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p. 546 - 556
(2017/01/03)
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- Transition metal complexes of 2-(2-(1H-benzo[d]imidazol-2-yl)hydrazono)propan-1-ol: Synthesis, characterization, crystal structures and anti-tuberculosis assay with docking studies
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Transition metal coordination complexes of Co(II), Ni(II), Cu(II) and Zn(II) with a newly designed ligand, 2-(2-(1H-benzo[d]imidazol-2-yl)hydrazono)propan-1-ol have been synthesized and characterized using various spectro-analytical techniques. The molecular structures of Co(II), Cu(II) and Zn(II) complexes are determined by single-crystal X-ray diffraction method. The metal to ligand stoichiometry has been found to be 1:2 in the case of Cobalt(II), Nickel(II) and Zinc(II) whereas 1:1 in the case of Copper(II) complex. The newly synthesized ligand and complexes have been assessed for their growth inhibiting potencies against H37Rv strain of Mycobacterium tuberculosis. The copper and cobalt complexes have emerged to be potent in vitro growth inhibitors of H37Rv. All the complexes are inhibiting the growth of other tested common microbial flora to a significantly lesser extent, making them selective towards H37Rv in the preliminary analysis. The consensus scores obtained by the docking studies of the molecules to the target protein enoyl acyl carrier protein reductase of M. tuberculosis H37Rv are in good agreement with the obtained MIC values.
- Kamat, Vinayak,Kokare, Dhoolesh,Naik, Krishna,Kotian, Avinash,Naveen,Dixit, Sheshagiri R.,Lokanath,Joshi, Shrinivas D.,Revankar, Vidyanand K.
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p. 225 - 237
(2017/04/17)
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- One-Pot, Metal-Free Conversion of Anilines to Aryl Bromides and Iodides
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A metal-free synthesis of aryl bromides and iodides from anilines via halogen abstraction from bromotrichloromethane and diiodomethane is described. This one-pot reaction affords aryl halides from the corresponding anilines in moderate to excellent yields without isolation of diazonium salts. The transformation has short reaction times, a simple workup, and insensitivity to moisture and air and avoids excess halogenation. DFT calculations support a SRN1 mechanism. This method represents a convenient alternative to the classic Sandmeyer reaction.
- Leas, Derek A.,Dong, Yuxiang,Vennerstrom, Jonathan L.,Stack, Douglas E.
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supporting information
p. 2518 - 2521
(2017/05/24)
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- Synthesis of 1,1-Diborylalkenes through a Br?nsted Base Catalyzed Reaction between Terminal Alkynes and Bis(pinacolato)diboron
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A method for the synthesis of 1,1-diborylalkenes through a Br?nsted base catalyzed reaction between terminal alkynes and bis(pinacolato)diboron has been developed. The procedure allows direct synthesis of functionalized 1,1-diborylalkenes from various ter
- Morinaga, Akira,Nagao, Kazunori,Ohmiya, Hirohisa,Sawamura, Masaya
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supporting information
p. 15859 - 15862
(2016/01/29)
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- Acid-base-responsive intense charge-transfer emission in donor-acceptor-conjugated fluorophores
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Herein we report on the synthesis and acid-responsive emission properties of donor-acceptor (D-A) molecules that contain a thienothiophene unit. 2-Arylthieno[3,2-b]thiophenes were conjugated with an N-methylbenzimidazole unit to form acid-responsive D-A-t
- Inouchi, Toshifumi,Nakashima, Takuya,Kawai, Tsuyoshi
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supporting information
p. 2542 - 2547
(2014/10/15)
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- Design and synthesis of benzimidazole-linked meta-substituted benzylidenes/benzyls as biologically significant new chemical entities
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meta-Linked thiazolidinedione (TZD)-and diethyl malonate (DEM)-based benzylidenes and methyl acetoacetate (MAA)-based benzyl moieties linked to the 2-position of N-methyl benzimidazole were synthesized. TZD-and DEM-based compounds were synthesized by condensation of 2,4-thiazolidinedone and DEM respectively with the corresponding 3-substituted benzaldehyde, whereas MAA-based compounds were obtained by halogen displacement with the corresponding 3-substituted phenol. These new chemical entities were designed to provide a balanced agonism at the peroxisome proliferator activated receptor alpha/gamma (PPARα/γ) in the management of type 2 diabetes: a move from glitazones to selective PPARγ modulators (SPPARγMs). Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.
- Verma, Raman K.,Mall, Rajiv,Ghosh, Prithwish,Kumar, Vijay
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supporting information
p. 1882 - 1895
(2013/06/04)
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- Trimethylsilyl chloride catalyzed synthesis of substituted benzimidazoles using two phase system under microwave conditions, and their antimicrobial studies
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A convenient method using TMSCl (20 mol%) and microwave-induced technique for the synthesis of various benzimidazole is described. This has reduced the reaction time drastically as well as improved the yield when compared to conventional heating. The synthesized compounds were evaluated for their in vitro antibacterial and antifungal activities against four strains each. Preliminary results indicated that, compounds 3e, 3f, 3g, 3k, 3m, 3n and 3o demonstrated very good antimicrobial activity, comparable to the first line standard drugs. The most effective compounds have exhibited activity at MIC of 6.25 μg/mL.
- Karuvalam, Ranjith P.,Haridas, Karickal R.,Shetty, Suchetha N.
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p. 1122 - 1125,4
(2020/08/24)
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- Selective benzimidazole inhibitors of the antigen receptor-mediated NF-κB activation pathway
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Dysregulated antigen receptor-mediated NF-κB activation can contribute to development of autoimmunity, chronic inflammation, and malignancy. A chemical biology screening strategy has identified a substituted benzimidazole that selectively inhibits antigen receptor-mediated NF-κB activation without blocking other NF-κB activation pathways. A library of analogs was synthesized and the structure-activity relationship and metabolic stability for the series is presented.
- Okolotowicz, Karl J.,Shi, Ranxin,Zheng, Xueying,MacDonald, Mary,Reed, John C.,Cashman, John R.
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scheme or table
p. 1918 - 1924
(2010/05/17)
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- Tetra butyl ammonium chloride catalyzed synthesis of substituted benzimidazoles under microwave conditions
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TBACl (10 mol %) was found to be a useful catalyst for the synthesis of substituted benzimidazoles. The method was proved to be simple, convenient and the product was isolated with good yield.
- Ranjith, P. Karuvalam,Siji,Divia,Karickal, R. Haridas
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experimental part
p. 589 - 593
(2011/01/12)
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- Polyhalogenobenzimidazoles: Synthesis and their inhibitory activity against casein kinases
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A series of novel polyhalogenated benzimidazoles have been prepared by exhaustive bromination of a variety of 2-substituted benzimidazoles. The efficacy of both new compounds and a number of their previously described cognates as inhibitors of casein kinases CK1, CK2 and G-CK was investigated. The type of N-1 alkyl substituent as well as introduction of a polyfluoroalkyl moiety at position 2 did not markedly influence the inhibitory efficacy toward CK2 of the respective 4,5,6,7-tetrabromobenzimidazole derivatives which conversely were almost ineffective toward CK1 and G-CK. However, 4,5,6,7-tetrabromobenzimidazoles substituted at position 2 with either chlorine, bromine or sulfur atom, while manifesting a still considerable inhibitory activity against CK2 (IC50 in the 0.49-0.93 μM range) proved to be potentially powerful inhibitors also against CK1 (IC50 in the 18.4-2.2 μM range).
- Andrzejewska, Mariola,Pagano, Mario A.,Meggio, Flavio,Brunati, Anna Maria,Kazimierczuk, Zygmunt
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p. 3997 - 4002
(2007/10/03)
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- Synthesis and thermolysis of heterocyclic 3-aza-3-ene-1,5-diynes(1).
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[reaction: see text] Simple, acyclic 3-aza-3-ene-1,5-diynes undergo an aza-Bergman rearrangement to a fleeting 2,5-didehydropyridine (2,5-ddp) intermediate that rapidly ring-opens to beta-alkynylacrylonitrile products. In an effort to access longer-lived 2,5-ddp intermediates, we have prepared heterocyclic 3-aza-3-ene-1,5-diynes. The thermolysis of one such heterocyclic aza-enediyne does not afford products derived from trapping a 2,5-ddp intermediate but rather cyclopropanes that appear to arise from a carbene intermediate and a product that appears to be a trapping product from a 2,3-ddp intermediate.
- Nadipuram, Asha K,David, Wendi M,Kumar, Dalip,Kerwin, Sean M
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p. 4543 - 4546
(2007/10/03)
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- Synthesis of a heterocyclic aza-enediyne and its DNA-cleavage properties
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The benzimidazolium salt 2, incorporating an aza-enediyne moiety, has been prepared and is shown to be a very effective DNA-cleavage agent under mild physiological conditions. Its mechanism of action is currently under investigation but may involve the generation of a diradical intermediate, DNA alkylation, or both. (C) 2000 Elsevier Science Ltd.
- David, Wendi M.,Kumar, Dalip,Kerwin, Sean M.
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p. 2509 - 2512
(2007/10/03)
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- Class III Antiarrhythmic Activity of Novel Substituted 4-benzamides and Sulfonamides
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The synthesis and Class III antiarrhythmic activity of a series of 4-benzamides and sulfonamides are described.Selected compounds shown a potent Class III activity and are devoid of effects on conduction both in vitro (dog Purkinje fibers) and in vivo (anesthetized dogs).Compounds having a 2-aminobenzimidazole group were found to be the most potent, and one compound having the heterocycle (5, WAY-123,398) was selected for further characterization.Compound 5 was shown to have good oral bioavailability and a favorable hemodynamic profile to produce a 3-fold increase of the ventricular fibrillation threshold and to terminate ventricular fibrillation, restoring sinus rhythm in anesthetized dogs.Voltage-clamp studies in isolated myocytes show that 5 is a potent and specific blocker of the delayed rectifier potassium current (IK) at concentrations that cause significant prolongation of action potential duration.
- Ellingboe, John W.,Spinelli, Walter,Winkley, Michael W.,Nguyen, Thomas T.,Parsons, Roderick W.,et al.
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p. 705 - 716
(2007/10/02)
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- A SUPERIOR SYNTHETIC METHOD FOR THE BROMINATION OF INDOLES AND BENZIMIDAZOLES.
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Brominated indoles and benzimidazoles are formed in very high yields and with substantial regioselectivity by use of a reagent system consisting of N-bromosuccinimide (NBS) and silica gel in dichloromethane.
- Mistry, Anil G.,Smith, Keith,Bye, Martin R.
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p. 1051 - 1054
(2007/10/02)
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