Structure, bioactivity and theoretical study of 1-cyano-N-p-tolylcyclo-propanecarboxamide

Liu, Xinghai; Chen, Pei-quan; He, Feng-Qi; Wang, Suhua; Song, Haibin; Li, Zhengming

doi:10.1007/s11224-007-9175-9

Cited by 11 publications

(6 citation statements)

References 17 publications

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“…No commercial herbicides and drugs targeting KARI have been developed. Until now, only 2‐dimethylphosphinoyl‐2‐ hydroxyacetate (HOE 704) (10), IpOHA (11), 1,2,3‐thiadiazoles (12), and cyclopropane‐1,1‐dicarboxylic acid (CPD) derivatives (13–16) were shown to be potential inhibitors targeting KARI (Figure 2). In addition, it is found HOE 704 (10), IpOHA (11) can inhibit tuberculosis much better than ATCC35801 (17), so these branched‐chain amino acids inhibitors became novel anti‐ tuberculosis medicine, and CPD (18,19) had good antifungal activities.…”

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High Throughput Receptor‐Based Virtual Screening Under ZINC Database, Synthesis, and Biological Evaluation of Ketol‐Acid Reductoisomerase Inhibitors

et al. 2010

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contributed equally to this work.Ketol-acid reductoisomerase (KARI; EC 1.1.1.86) catalyzes the second common step in branchedchain amino acid biosynthesis. This enzyme is an important target for drug design. Based on the crystal structure of ketol-acid reductoisomerase/ N-hydroxy-N-isopropyloxamate (IpOHA) complex, we have carried out high throughput receptorbased virtual screening of the ZINC/drug like database (2 000 000 compounds) to look for novel inhibitors of KARI for the first time. Some novel compounds were found to inhibit rice KARI in vitro among 15 procured compounds. This method can provide useful information for further design and discovery of KARI inhibitors.

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High Throughput Receptor‐Based Virtual Screening Under ZINC Database, Synthesis, and Biological Evaluation of Ketol‐Acid Reductoisomerase Inhibitors

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“…These compounds are also widely applied in medicine [3] and agriculture [4]. In view of these facts and in continuation of our interest in the agriculture,we attempted to synthesize aseries of amide derivatives, some of which have comparatively high fungicidal activity.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of methyl-4-(4-ethylbenzamido)-2-sulfamoylbenzoate, C17H18N2O5S

Wang¹

2009

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of materialReagents and solvents used were of commercially available quality. The title compound was prepared similarly to the reported procedure [1]. Dropwise 4-ethylbenzoyl chloride (7.5 mmol) was added to methyl 4-amino-2-sulfamoylbenzoate (7.50 mmol) in THF (20 ml) solution, then refluxed for 4h.Colorless single crystals suitable for X-ray diffraction were obtained by recrystallization from amixture of ethyl acetate and petroleum ether. Experimental detailsThe Hatoms bonded to Cand Natoms were positioned geometrically and refined using ar iding modelThe Hatoms bonded to Oatoms were located in difference Fourier maps and refined with O-H distance restraints of 0.85(2) Å and DiscussionAmides are very useful starting materials for the synthesis of various bioactive molecules [2]. These compounds are also widely applied in medicine [3] and agriculture [4]. In view of these facts and in continuation of our interest in the agriculture,we attempted to synthesize aseries of amide derivatives, some of which have comparatively high fungicidal activity.The benzene ring in the title crystal structure is planar. The carboxamide moiety is coplanar with the benzene ring [dihedral angle 176.2(3)°]. The interatomic distance for C9-O1 is 1.218(4) Å,revealing anormal C=O double bond. In addition, the X-ray data also indicate intermolecular and intramolecular Hbonding interactions.

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“…Liu et al [261] in the next article report on structure, bioactivity, and theoretical study of 1-cyano-N-p-tolylcyclopropanecarboxamide. The thermochemistry of cyclopropanes has been of interest to those concerned with the energetics of strained rings [262].…”

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Interplay of thermochemistry and Structural Chemistry, the journal (volume 18, 2007) and the discipline

Ponikvar

Liebman

2008

Struct Chem

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In this study, we relate the contents of the journal Structural Chemistry for the calendar year 2007 and thermochemistry. The year's articles were briefly summarized and a thermochemical comment written to supplement them. Frequently questions were asked and future research was suggested.Keywords Structural Chemistry Á Thermochemistry Á Thermodynamics Á Enthalpy of formation Á Enthalpy of phase change Á Enthalpy of reaction As practiced disciplines, structural chemistry and thermochemistry are very often unrelated. In this study, these disciplines are linked as relations are explicitly made using the contents of the journal Structural Chemistry (Vol. 18) for the calendar year 2007 as a scaffold for our analysis, for our selected articles in the discipline of structural chemistry. These studies have been reviewed by us, where we give them a thermochemical flavor. While this commentary is most generally written in terms of brief summaries of literature papers involving enthalpies of formation and/or reaction, not uncommonly we raise questions and even suggest possible future research. We are not, however, going to give a thermochemical slant on book reviews, honorary dedications, and obituaries although these works will be cited in our text.As such, this article is a sequel to our earlier related reviews of Structural Chemistry for the calendar years 2000 through 2004 [1-5]. Reviews for 2005 and 2006 are currently being prepared. Issue 1In the first article in the first issue of Structural Chemistry for 2007, Hargittai [6] asserted that while research is currently usually carried out in big groups, the most important ideas, observations and discoveries still belong to individuals who have to bring down dogmas or open entirely new areas in science. This may bring solace to the thermochemical community in which research groups are generally small, and the number of new practitioners sadly few.In the past decade, the crystal engineering of multidimensional arrays and networks containing metal ions has achieved considerable progress because of the increased interest in the potential utility of these compounds as zeolite-like materials [7-11], catalysts [12], or magnetic materials [13][14][15]. The thermochemistry of these species is complicated by their inherent complexity: however, estimation approaches of their key thermochemical quantities are increasingly reliable [16]. In the second article of this issue, by Wang et al. [17], the versatility of malonate dianion as a ligand for the construction of extended networks with different topologies dependent on the coordination geometry of the metal ion was discussed. The synthesis and structure of a novel malonate-bridged copper(II) compound in which copper(II) ions have two different coordination environments in a novel three-dimensional (3D) network was described. Metal malonates have been studied from a

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Structure, bioactivity and theoretical study of 1-cyano-N-p-tolylcyclo-propanecarboxamide

Cited by 11 publications

References 17 publications

High Throughput Receptor‐Based Virtual Screening Under ZINC Database, Synthesis, and Biological Evaluation of Ketol‐Acid Reductoisomerase Inhibitors

High Throughput Receptor‐Based Virtual Screening Under ZINC Database, Synthesis, and Biological Evaluation of Ketol‐Acid Reductoisomerase Inhibitors

Crystal structure of methyl-4-(4-ethylbenzamido)-2-sulfamoylbenzoate, C17H18N2O5S

Interplay of thermochemistry and Structural Chemistry, the journal (volume 18, 2007) and the discipline

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