- Synthesis and application of photo-active carboxymethyl cellulose derivatives
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In this work, the polysaccharide carboxymethyl cellulose (CMC) was first activated via periodate oxidation then modified by insertion of photo-active cinnamic acid hydrazide moieties to finally produce the photo-crosslinkable CMC-CM with various extents of functionalizations. The chemical structures of the manufactured polymeric materials were entirely investigated utilizing FTIR, 1H, 13C NMR, and UV-vis spectra. Upon irradiation in UV light, the progress and kinetics of the cross-linking were detected using UV-vis spectra. Moreover, the crystallinity changes before and after chemical modification and subsequent UV irradiation were examined by XRD spectra. Also, the obtained hydrogels with various cross-linking densities were freeze dried to visualize the morphological changes using SEM. In addition, the rheological experiments indicated the improvement of the hydrogel mechanical properties by increasing both UV irradiation time and degree of cinnamate functionalization. The obtained hydrogel exhibited good swelling, gelation and biodegradation properties, which indicate a promising potential in different biomedical applications.
- Monier,Abdel-Latif,Ji
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Read Online
- Ion-exchange resin catalysts in the liquid-phase hydrazinolysis of cinnamic acid
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The catalytic activity of a synthetic ion-exchange resins has been studied in the reaction of cinnamic acid with hydrazine (aqueous medium, 363 K, 1.0–2.5 h) yielding the corresponding hydrazide. Efficient catalysts for the process are the anion-exchange resins AV-17-8 and AN-31. The modifying effect of the substrate—hydrazine hydrate—on the catalytic properties of the ion-exchange systems has been demonstrated. On the basis of IR spectroscopic studies, a plausible process mechanism was suggested. It involves polymer-bound quaternary ammonium ions of the anion exchanger.
- Dzhumadullaeva,Baeshov
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Read Online
- ANTIMICROBIAL AGENTS AND COMPOSITIONS AND USES THEREOF
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Described herein are compounds that act as antimicrobial agents, compositions comprising these compounds, and methods of their use in to treating infections caused by Helicobacter pylori (H. pylori) or killing or inhibititing the growth of H. pylori.
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Paragraph 0256-0257
(2021/04/01)
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- Synthesis, characterization and study of mesomorphic behavior of new bent and linear core compounds containing heterocyclic rings
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The article presents the synthesis and liquid crystalline properties of some of new bent and linear core compounds containing a 1,3,4-oxadiazole, piperazine and thiazolidin-4-one rings as a central core. The new synthesized compounds were characterized by elemental analysis and FTIR, 1HNMR and mass spectroscopy). The liquid crystalline properties were studied by polarized optical microscopy and differential scanning calorimetry. All Schiff bases compounds with 1,3,4-oxadiazole and piprzaine ring in central core presented liquid crystalline properties. The liquid crystallinity of compounds containing 1,3,4-oxadiazole and thiazolidin-4-one rings as a central core were found depending on the type of terminal substituents.
- Al-Dujaili, Ammar H.,Karam, Nisreen H.,Shanshal, Alaa K.
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- Novel fluorozoone-like fluorinion probe based on flavonoids
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The invention discloses a preparation method of a novel fluorozoone-like visible fluorinion probe which is prepared from flavonoids of a formula I shown in the description and a 3-phenylacrylic acid type derivative. The preparation method comprises the fo
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Paragraph 0026; 0027
(2020/02/06)
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- Identification of novel functionalized carbohydrazonamides designed as chagas disease drug candidates
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Background: Although several research efforts have been made worldwide to discover novel drug candidates for the treatment of Chagas disease, the nitroimidazole drug benznidazol remains the only therapeutic alternative in the control of this disease. However, this drug presents reduced efficacy in the chronic form of the disease and limited safety after long periods of admini-stration, making it necessary to search for new, more potent and safe prototypes. Objective: We described herein the synthesis and the trypanocidalaction of new functionalized carbohydrazonamides (2-10) against trypomastigote forms of Trypanosoma cruzi. Methods: These compounds were designed through the application of molecular hybridization concept between two potent anti-T. cruzi prototypes, the nitroimidazole derivative megazol (1) and the cinnamyl N-acylhydrazone derivative (14) which have been shown to be twice as potent in vitro as benznidazole. Results: The most active compounds were the (Z)-N'-((E)-3-(4-nitrophenyl)-acryloyl)-1-methyl-5-nitro-1H-imidazol-2-carbohydrazonamide (6) (IC50 =9.50 μM) and the (Z)-N'-((E)-3-(4-hydroxyphe-nyl)-acryloyl)-1-methyl-5-nitro-1H-imidazol-2-carbohydrazonamide (8) (IC50 =12.85 μM), which were almost equipotent to benznidazole (IC50 =10.26 μM) used as standard drug. The removal of the amine group attached to the imine subunit in the corresponding N-acylhydrazone derivatives (11-13) resulted in less potent or inactive compounds. The para-hydroxyphenyl derivative (8) presented also a good selectivity index (SI = 32.94) when tested against mammalian cells from Swiss mice. Conclusion: The promising trypanocidal profile of new carbohydrazonamide derivatives (6) and (8) was characterized. These compounds have proved to be a good starting point for the design of more effective trypanocidal drug candidates.
- Do Nascimento, Mayara S. S.,Camara, Vitória R. F.,da Costa, Juliana S.,Barbosa, Juliana M. C.,Lins, Alessandra S. M.,Salom?o, Kelly,de Castro, Solange L.,Carvalho, Samir A.,da Silva, Edson F.,Fraga, Carlos A. M.
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p. 774 - 783
(2020/08/19)
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- Cinnamoyl-N-Acylhydrazone-Donepezil Hybrids: Synthesis and Evaluation of Novel Multifunctional Ligands Against Neurodegenerative Diseases
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Abstract: A new series of ten multifunctional Cinnamoyl-N-acylhydrazone-donepezil hybrids was synthesized and evaluated as multifunctional ligands against neurodegenerative diseases. The molecular hybridization approach was based on the combination of 1-b
- Ortiz, Cindy Juliet Cristancho,Damasio, Caio Miranda,Pruccoli, Letizia,Nadur, Nathália Fonseca,de Azevedo, Luciana Luiza,Guedes, Isabella Alvim,Dardenne, Laurent Emmanuel,Kümmerle, Arthur Eugen,Tarozzi, Andrea,Viegas, Claudio
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p. 3003 - 3020
(2020/10/22)
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- Synthesis and Docking Study of N-(Cinnamoyl)- N′-(substituted)acryloyl Hydrazide Derivatives Containing Pyridinium Moieties as a Novel Class of Filamentous Temperature-Sensitive Protein Z Inhibitors against the Intractable Xanthomonas oryzae pv. oryzae Infections in Rice
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Xanthomonas oryzae pv. oryzae (Xoo) is an offensive phytopathogen that can invade a wide range of plant hosts to develop bacterial diseases, including the well-known rice bacterial leaf blight. However, few agrochemicals have been identified to effectively prevent and eliminate Xoo-induced diseases. Thus, designing novel antibacterial compounds on the basis of the potential targets from Xoo may lead to the discovery of highly efficient and innovative anti-Xoo agents. Filamentous temperature-sensitive protein Z (FtsZ), an important functional protein in the progression of cell division, has been widely reported and exploited as a target for creating antibacterial drugs in the field of medicine. Therefore, the fabrication of innovative frameworks targeting XooFtsZ may be an effective method for managing bacterial leaf blight diseases via blocking the binary division and reproduction of Xoo. As such, a series of novel N-(cinnamoyl)-N′-(substituted)acryloyl hydrazide derivatives containing pyridinium moieties were designed, and the anti-Xoo activity was determined. The bioassay results showed that compound A7 had excellent anti-Xoo activity (EC50 = 0.99 mg L-1) in vitro and distinct curative activity (63.2% at 200 mg L-1) in vivo. Further studies revealed that these designed compounds were XooFtsZ inhibitors, validating by the reduced GTPase activity of recombinant XooFtsZ, the nonfilamentous XooFtsZ assembly observed in the TEM images, and the prolonged Xoo cells from the fluorescence patterns. Computational docking studies showed that compound A7 had strong interactions with ASN34, GLN193, and GLN197 residues located in the α helix regions of XooFtsZ. The present study demonstrates the developed FtsZ inhibitors can serve as agents to control Xoo-induced infections.
- Feng, Yu-Mei,Li, Zhong,Liu, Li-Wei,Ma, Hao-Dong,Qi, Pu-Ying,Shao, Wu-Bin,Wang, Pei-Yi,Wang, Yi,Wu, Zhi-Bing,Yang, Song,Zhou, Xiang
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p. 8132 - 8142
(2020/09/02)
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- Novel 1,3,4-oxadiazole derivatives containing a cinnamic acid moiety as potential bactericide for rice bacterial diseases
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Rice bacterial leaf blight and leaf streak are two important bacterial diseases of rice, which can result in yield loss. Currently, effective antimicrobials for rice bacterial diseases are still lacking. Thus, to develop highly effective and low-risk bact
- Wang, Shaobo,Gan, Xiuhai,Wang, Yanju,Li, Shaoyuan,Yi, Chongfen,Chen, Jixiang,He, Fangcheng,Yang, Yuyuan,Hu, Deyu,Song, Baoan
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- Colorimetric and ratiometric sensors derivated from natural building blocks for fluoride ion detection
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Three novel colorimetric and ratiometric probes (SH-1~3) for fluoride ion detection were designed and synthesized from nature small molecules. Obvious yellow-to-orange color change of these probes in the THF was achieved only in presence of F?
- Shi, Heng,Zhao, Fengfei,Chen, Xinghan,Yang, Shilong,Xing, Jieni,Chen, Hongjin,Zhang, Rui,Liu, Jian
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supporting information
(2019/11/03)
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- Synthesis of N′-propylhydrazide analogs of hydroxamic inhibitors of histone deacetylases (HDACs) and evaluation of their impact on activities of HDACs and replication of hepatitis C virus (HCV)
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N′-Propylhydrazide analogs of hydroxamic inhibitors of histone deacetylases (HDACs), including tubastatin A, vorinostat and belinostat, were synthesized. All prepared compounds inhibited HDAC1/2/3, but not HDAC6, except for one hydrazide analog of HDAC4/5/7 inhibitor that was completely inactive. A novel 4-substituted derivative of N′-propylbenzohydrazide with extremely high anti-HCV activity was discovered.
- Kozlov, Maxim V.,Konduktorov, Konstantin A.,Shcherbakova, Anastasia S.,Kochetkov, Sergey N.
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supporting information
p. 2369 - 2374
(2019/06/17)
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- Design, synthesis and evaluation against Chikungunya virus of novel small-molecule antiviral agents
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Chikungunya virus is a re-emerging arbovirus transmitted to humans by mosquitoes, responsible for an acute flu-like illness associated with debilitating arthralgia, which can persist for several months or become chronic. In recent years, this viral infection has spread worldwide with a previously unknown virulence. To date, no specific antivirals treatments nor vaccines are available against this important pathogen. Starting from the structures of two antiviral hits previously identified in our research group with in silico techniques, this work describes the design and preparation of 31 novel structural analogues, with which different pharmacophoric features of the two hits have been explored and correlated with the inhibition of Chikungunya virus replication in cells. Structure-activity relationships were elucidated for the original scaffolds, and different novel antiviral compounds with EC50 values in the low micromolar range were identified. This work provides the foundation for further investigation of these promising novel structures as antiviral agents against Chikungunya virus.
- Tardugno, Roberta,Giancotti, Gilda,De Burghgraeve, Tine,Delang, Leen,Neyts, Johan,Leyssen, Pieter,Brancale, Andrea,Bassetto, Marcella
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p. 869 - 874
(2018/01/18)
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- HISTONE DEACETYLASE INHIBITORS AND USES THEREOF
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Provided herein are compounds of the formula (I) as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of cancer.
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Page/Page column 22; 25; 26
(2018/04/27)
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- Synthesis, nematicidal evaluation, and 3D-QSAR analysis of novel 1,3,4-oxadiazole-cinnamic acid hybrids
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A series of novel 1,3,4-oxadiazole-cinnamic acid hybrids were synthesized. The bioassays results indicated that compounds 1, 2, 7, and 8 showed excellent nematicidal activities against Tylenchulus semipenetrans with LC50,48h values of 9.7 ± 1.6, 15.6 ± 2.8, 8.0 ± 0.5, and 19.8 ± 2.9 mg/L, respectively, which were higher than those of avermectin (32.6 ± 4.5 mg/L) and fosthiazate (67.8 ± 1.7 mg/L). Low-toxicity compound 26, with excellent nematicidal activity in vitro (LC50,48h = 8.2 ± 1.2 mg/L), was designed on the basis of the predictive CoMFA (q2 = 0.795, r2 = 0.921) and CoMSIA (q2 = 0.762, r2 = 0.912) models. The control effect of compound 26 was 69.8% at an effective dose of 1.0 g per plant in a field experiment, which was superior to that of fosthiazate (67.2%). This work indicated that 1,3,4-oxadiazole-cinnamic acid hybrids may be used as potential nematicides.
- Chen, Jixiang,Chen, Yongzhong,Gan, Xiuhai,Song, Baojing,Hu, Deyu,Song, Baoan
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p. 9616 - 9623
(2018/09/18)
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- Styryl-containing 1,3,4-oxadiazole thioether compound, as well as preparation method and application thereof
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The invention discloses a styryl-containing 1,3,4-oxadiazole thioether compound. The structural general formula (I) is as follows: R1 is hydrogen, 4-methoxyl, 4-chlorine, 4-fluorine or 4-bromine; R is methyl, ethyl, benzyl, 2,5-dichlorobenzyl, 4-fluorobenzyl, 4-hlorobenzyl, 2-methylbenzyl, 4-nitrobenzyl, 1,1,2-trifluoro-butenyl or the like. The styryl-containing 1,3,4-oxadiazole thioether compound has activities of killing citrus nematode and meloidogyne incognita chitwood. (The formula (I) is as shown in the description.).
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Paragraph 0049; 0050
(2017/08/18)
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- Synthesis of piplartine analogs and preliminary findings on structure–antimicrobial activity relationship
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In this work it is described the synthesis, characterization and antimicrobial and toxicity evaluation of a series of analogs of piplartine, a piperamide found in Piper sp. The compounds structures were confirmed by infrared spectroscopy, 1H, 13C nuclear magnetic resonance, high resolution mass spectroscopy and were evaluated against strains of Candida spp., Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa. Derivative 24 was almost four-fold more potent (IC50: 48.83 μM) and five-fold less toxic (SI > 3) than piplartine (IC50: 189.2 μM; SI: 0.21) against Candida krusei, as well as two-fold more potent than fluconazole (IC50: 104.48 μM). This compound was also active against Candida tropicalis at 97.67 μM. Benzoyl derivative 17 was three-fold more potent (IC50: 85.2 μM) and more than five-fold less toxic (CC50: 231.71 μM) than piplartine (IC50: 315.33 μM and CC50: 41.14 μM) against Staphylococcus aureus. Given these findings, we have found analogs of piplartine which can be assumed as prototypes for the optimization and the development of new antimicrobial (compounds 24 and 17) agents.
- Fregnan, Antonio Maciel,Brancaglion, Guilherme Andrade,Galv?o, Alexandre Francisco Cerqueira,D’Sousa Costa, Cinara Oliveira,Moreira, Diogo Rodrigo Magalh?es,Soares, Milena Botelho Pereira,Bezerra, Daniel Pereira,Silva, Naiara Chaves,de Souza Morais, Stella Maria,Oliver, Josidel Concei??o,Dias, Amanda Latercia Tranches,Coelho, Luiz Felipe Leomil,Carvalho, Diogo Teixeira,Dias, Danielle Ferreira,de Souza, Thiago Belarmino
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p. 603 - 614
(2017/02/15)
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- Development of Allosteric Hydrazide-Containing Class i Histone Deacetylase Inhibitors for Use in Acute Myeloid Leukemia
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One of the biggest hurdles yet to be overcome for the continued improvement of histone deacetylase (HDAC) inhibitors is finding alternative motifs equipotent to the classic and ubiquitously used hydroxamic acid. The N-hydroxyl group of this motif is highly subject to sulfation/glucoronidation-based inactivation in humans; compounds containing this motif require much higher dosing in clinic to achieve therapeutic concentrations. With the goal of developing a second generation of HDAC inhibitors lacking this hydroxamate, we designed a series of potent and selective class I HDAC inhibitors using a hydrazide motif. These inhibitors are impervious to glucuronidation and demonstrate allosteric inhibition. In vitro and ex vivo characterization of our lead analogues' efficacy, selectivity, and toxicity profiles demonstrate that they possess low nanomolar activity against models of acute myeloid leukemia (AML) and are at least 100-fold more selective for AML than solid immortalized cells such as HEK293 or human peripheral blood mononuclear cells.
- McClure, Jesse J.,Zhang, Cheng,Inks, Elizabeth S.,Peterson, Yuri K.,Li, Jiaying,James Chou
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p. 9942 - 9959
(2016/11/19)
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- Dibenzo-azepine-dione anti-tumor compounds and preparation method thereof
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The invention provides dibenzo-azepine-dione anti-tumor compounds and a preparation method thereof, belongs to the technical field of medicines and particularly relates to compounds with specific chemical structures with anti-tumor activity. General formulae of the compounds include a general formula I, a general formula II, a general formula III and a general formula IV. The invention further provides an application of the compounds in anti-tumor and the preparation method. Tests of various tumor cell lines such as human lung cancer cells and human gastric carcinoma cells prove that the compounds have the tumor activity inhibition effect. The raw materials of the compounds are easily available, the preparation method is simple, and experiments prove that the compounds have good anti-cancer effect and have good application prospect in the field of design, research and development of anti-tumor drugs.
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Paragraph 0131; 0134; 0135
(2016/10/07)
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- Oxidative cyclization of N-aroylhydrazones to 2-(2-arylethenyl)-1,3,4-oxadiazoles using DDQ as an efficient oxidant
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A series of novel 5-aryl-2-(2-arylethenyl)-1,3,4-oxadiazoles were synthesized by the 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) promoted oxidative cyclization of N′-(arylmethylidene)-3-arylacrylohydrazides. A facile and efficient one-pot protocol using th
- Jasiak, Karolina,Kudelko, Agnieszka
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supporting information
p. 5878 - 5881
(2015/11/02)
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- NEW GUANIDINE DERIVATIVES IN CINNAMIC SERIES
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The invention relates to novel guanidine derivatives in the cinnamic series of general formula (I): The invention also relates to the process for preparing said guanidine derivatives and also to synthetic intermediates. Finally, the invention relates to t
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Paragraph 0126; 0127; 0128; 0129; 0130
(2013/07/05)
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- 2-(Quinolin-4-ylthio)-1,3,4-oxadiazole derivatives: Design, synthesis, antibacterial and antifungal studies
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A series of novel hybrid 2-(7-chloroquinolin-4-ylthio)-5-(substituted)-1,3, 4-oxadiazole derivatives have been designed, synthesized which contains different pharmacophores like quinoline and 1,3,4-oxadiazole linked via sulfur atom. All the newly synthesized derivatives have been characterized by IR, 1H NMR, 13C NMR spectral and elemental analysis. Further, All the final synthesized scaffolds have been subjected to in vitro antimicrobial activity against several bacteria (E.coli, P.aeruginosa, S.aureus, S.pyogenus) and fungi (C.albicans, A.niger, A.clavatus) using broth dilution technique. Among the compounds tested, compounds 3f substituted with coumarin analogue and 3b with amine group at second position of phenyl to oxadiazole moiety are found to be most potent.
- Modh, Rahul P,Shah, Dhruvin,Chikhalia, Kishor H
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p. 1318 - 1324
(2014/01/06)
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- In situ generation of diimide from hydrazine and oxygen: Continuous-flow transfer hydrogenation of olefins
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No catalyst required! A highly efficient, catalyst-free process to generate diimide in situ from hydrazine monohydrate and molecular oxygen for the selective reduction of alkenes has been developed. The use of a gas-liquid segmented flow system allowed safe operating conditions and dramatically enhanced this atom-economical reaction, resulting in short processing times. Copyright
- Pieber, Bartholomaeus,Martinez, Sabrina Teixeira,Cantillo, David,Kappe, C. Oliver
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supporting information
p. 10241 - 10244
(2013/10/21)
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- Design and synthesis of new (E)-cinnamic N-acylhydrazones as potent antitrypanosomal agents
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We report herein the synthesis and trypanocidal profile of new (E)-cinnamic N-acylhydrazones (NAHs) designed by exploiting molecular hybridization between the potent cruzain inhibitors (E)-1-(benzo[d][1,3]dioxol-5-yl)-3-(4-bromophenyl) prop-2-en-1-one and (E)-3-hydroxy-N'-((2-hydroxynaphthalen-1-yl)methylene)-7- methoxy-2-naphthohydrazide. These derivatives were evaluated against both amastigote and trypomastigote forms of Trypanosoma cruzi and lead us to identify two compounds that were approximately two times more active than the reference drug, benznidazole, and with good cytotoxic index. Although designed as cruzain inhibitors, the weak potency displayed by the best cinnamyl NAH derivatives indicated that another mechanism of action was likely responsible for their trypanocide action.
- Carvalho, Samir A.,Feitosa, Larisse O.,Soares, Marcio,Costa, Thadeu E.M.M.,Henriques, Maria G.,Salomao, Kelly,De Castro, Solange L.,Kaiser, Marcel,Brun, Reto,Wardell, James L.,Wardell, Solange M.S.V.,Trossini, Gustavo H.G.,Andricopulo, Adriano D.,Da Silva, Edson F.,Fraga, Carlos A.M.
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experimental part
p. 512 - 521
(2012/09/07)
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- Antimicrobial evaluation of 4-methylsulfanyl benzylidene/3-hydroxy benzylidene hydrazides and QSAR studies
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A series of 4-methylsulfanyl benzylidene/3-hydroxy benzylidene hydrazides (1-20) was synthesized and tested for in vitro antimicrobial activity against S. aureus, B. subtilis, E. coli, C. albicans and A. niger. The results of antimicrobial studies indicated that 3-phenylacrylic acid-(3-hydroxybenzylidene) -hydrazide, 16, was the most effective as it showed both bactericidal and fungicidal properties and other compounds possessed bacteriostatic/fungistatic activity. The multi-target QSAR model demonstrated that the topological parameter, Balaban topological index (J) is effective in describing the antimicrobial activity of synthesized substituted hydrazides. Springer Science+Business Media, LLC 2010.
- Kumar, Davinder,Narang, Rakesh,Judge, Vikramjeet,Kumar, Devinder,Narasimhan, Balasubramanian
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experimental part
p. 382 - 394
(2012/08/27)
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- Microwave-assisted synthesis of 2-styryl-1,3,4-oxadiazoles from cinnamic acid hydrazide and triethyl orthoesters
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A novel and efficient synthesis of 2-styryl-1,3,4-oxadiazoles by cyclocondensation of cinnamic acid hydrazide and triethyl orthoesters under microwave irradiation is reported.
- Kudelko, Agnieszka,Zieliński, Wojciech
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supporting information; experimental part
p. 76 - 77
(2012/01/05)
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- Synthesis, antimicrobial evaluation and QSAR studies of 3-ethoxy-4-hydroxybenzylidene/4-nitrobenzylidene hydrazides
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A series of 3-ethoxy-4-hydroxybenzylidene/4-nitrobenzylidene hydrazides (1-20) was synthesized and tested for in vitro antimicrobial activity. The results of antimicrobial studies indicated that the compounds having dinitro, methoxy, hydroxy and nitro substituents on phenyl ring of the aromatic acids were most active ones. The QSAR investigation indicated the importance of the topological parameter, third order molecular connectivity index ( 3χ) in describing the antimicrobial activity of synthesized hydrazides.
- Kumar, Davinder,Kapoor, Archana,Thangadurai, Ananda,Kumar, Pradeep,Narasimhan, Balasubramanian
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experimental part
p. 1293 - 1296
(2012/01/07)
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- 2-thiophenecarbohydrazides: A novel efficient method for the synthesis of 2-thiophenecarbohydrazide
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Hydrazinolysis of carboxylic acid esters in alcoholic solutions is the standard method for preparing carbohydrazides (carboxylic hydrazides). Here we report an efficient process, involving the reaction of activated esters or amides with hydrazine, for the preparation of thiophenecarbohydrazides in yields larger than 90% and high purity. With this new method, a series of heteroaryl-, aryl-, or aralkyl- substituted carbohydrazides were synthesized and characterized. The X-ray crystal structure of 2-thiophenecarbohydrazide (thiophene-2-carboxylic hydrazide, 2-thenoyl-hydrazine) has revealed that it crystallizes in the monoclinic system, space group P21/c, with cell parameters of a = 6.1202(2), b = 8.3907(3), c = 12.5332(5) A, β = 98.6577(11)?, Z = 4, R(F) = 0.0455 and wR(F2) = 0.1805, T = 293 K.
- Elshaarawy, Reda F.M.,Janiakb, Christoph
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experimental part
p. 1202 - 1208
(2012/03/09)
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- Benzylidene/2-chlorobenzylidene hydrazides: Synthesis, antimicrobial activity, QSAR studies and antiviral evaluation
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A series of benzylidene hydrazides (1-20) was synthesized and tested, in vitro, for antibacterial, antifungal and antiviral activities. The microbial screening results indicated that compounds having chloro and nitro substituents were the most active ones. The antiviral evaluation depicted that compounds 9 and 19 were active against Vesicular stomatitis virus (VSV) in HeLa cell cultures. QSAR investigations indicated that the multi-target QSAR model was effective in describing the antimicrobial (antibacterial and antifungal) activity over the one-target QSAR models. Further the mt-QSAR model indicated that the topological parameters, second order molecular connectivity index (2χ) and third order Kier's alpha shape index (κα3) are effective in describing the antimicrobial activity of synthesized hydrazides.
- Kumar, Davinder,Judge, Vikramjeet,Narang, Rakesh,Sangwan, Sonia,De Clercq, Erik,Balzarini, Jan,Narasimhan, Balasubramanian
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experimental part
p. 2806 - 2816
(2010/08/20)
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- Synthesis and cyclisation of 1,4-disubstituted semicarbazides
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Semicarbazides, besides possessing medicinal properties, also find wide applications in agriculture and industry. We report in this article the synthesis of the four 1,4-disubstituted semicarbazides: 1-cinnamoyl-4-phenyl semicarbazide (1), 1-oleyl-4-phenyl semicarbazides (2), 1,1',1''-tricitryl-4,4', 4''-triphenyl semicarbazide (3) and 1-benzoyl-4-phenyl semicarbazide (4), by the condensation of four different hydrazides: cinnamic acid hydrazide (5), oleic acid hydrazide (6), citric acid hydrazide (7) and benzoic acid hydrazide (8). The acid hydrazides were prepared by the condensation of four different acids with phenyl isocyanate. The semicarbazides were also subjected to acid catalysed intramolecular cyclisation. The cyclisation of (1) and (2) afforded substituted 1,3,4-oxadizoles: 2-cinnamoyl-5-aminophenyl 1,3,4-oxadizoles (9) and 2-oleyl-5-aminophenl 1,3,4-oxadizoles (10), respectively, in high yield, while no cyclisation occurred in the cases of (3) and (4). The products in each case have been identified on the basis of melting points and IR spectral studies.
- Asghar, Syeda Farina,Yasin, Khawaja Ansar,Aziz, Shahid
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experimental part
p. 315 - 325
(2010/07/06)
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- Structure-activity relationship studies of salubrinal lead to its active biotinylated derivative
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The synthesis and structure-activity relationships (SAR) of salubrinal, a small molecule that protects cells from apoptosis induced by endoplasmic reticulum (ER) stress, are described. It is revealed that the trichloromethyl group greatly contributes to the activity. Based on the SAR results, salubrinal was converted into a biotinylated derivative which retains activity and can be used as a biological tool for target identification.
- Long, Kai,Boyce, Michael,Lin, He,Yuan, Junying,Ma, Dawei
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p. 3849 - 3852
(2007/10/03)
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- Esters, amides and substituted derivatives of cinnamic acid: Synthesis, antimicrobial activity and QSAR investigations
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A series of esters (Ia-k), substituted derivatives (II a-d) and amides (IIIa-q) of cinnamic acid were synthesized and evaluated as antibacterial and antifungal agents. All the derivatives belonging to the series I, II and III showed antimicrobial activity comparable to the standard. Compounds If and IIc proved to be the most effective compounds. Quantitative structure-activity relationship (QSAR) investigation with multiple linear regression analysis was applied to find a correlation between different calculated physicochemical parameters of the compounds and biological activity. The quantitative models relating the structural features of cinnamic acid derivatives Ia-k, II a-d and IIIa-q and their antimicrobial activity showed that Gram negative Escherichia coli and Candida albicans (fungus) were the most sensitive microorganisms.
- Narasimhan, Balasubramanian,Belsare, Deepak,Pharande, Devayani,Mourya, Vishnukant,Dhake, Avinash
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p. 827 - 834
(2007/10/03)
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- An efficient microwave-assisted one-pot conversion of carboxylic acids into hydrazides
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A microwave-assisted protocol was developed to prepare hydrazides from corresponding carboxylic acids in good yields through transacylation with acethydrazide.
- Peng, Yanqing,Song, Gonghua
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p. 768 - 769
(2007/10/03)
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- A new procedure for preparation of carboxylic acid hydrazides
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The standard method for preparing carboxylic acid hydrazides is hydrazinolysis of esters in alcoholic solutions. However, when applied to α,β-unsaturated esters, the main product typically is the pyrazolidinone resulting from an undesired Michael-type cyclization. Other alternative methodologies reported for direct preparation of hydrazides from acids are inefficient. We developed an efficient and general process, involving preforming activated esters and/or amides followed by reaction with hydrazine, for the preparation of hydrazides including those of α,β-unsaturated acids. This process gives the desired hydrazides in excellent yield and purity under mild conditions.
- Zhang, Xini,Breslav, Michael,Grimm, Jeffrey,Guan, Kailin,Huang, Aihua,Liu, Fuqiang,Maryanoff, Cynthia A.,Palmer, David,Patel, Mitul,Qian, Yun,Shaw, Charles,Sorgi, Kirk,Stefanick, Stephen,Xu, Dawei
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p. 9471 - 9474
(2007/10/03)
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- 3,6-Bis(2-arylethenyl)-1,2,4,5-tetrazines - Synthesis, LC Properties and Photochemistry
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The (E,E)-3,6-bis(2-arylethenyl)-1,2,4,5-tetrazines 8 were prepared in a synthetic sequencve starting with aromatic aldehydes 1 and cinnamic acids 2, respectively (Scheme 1).The rod-like conjugated molecules represent clamitic mesogens as well as extended chromophores.Hence, we investigated the formation of liquid crystals, achieved by the introduction of long flexlible side chains, and the photochemical behaviour that is characterized by the fragmentation of the central ring (Scheme 3).
- Lifka, Thorsten,Meier, H.
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p. 641 - 646
(2007/10/03)
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