- Crystal structure, thermal behavior, luminescence and theoretical calculation of a new Pb(II) coordination complex
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In this report, a new coordination complex Pb(CDIPT)2(L)2 (CDIPT= 10?chloro?2-(2,4-dichlorophenyl)-1H-imidazo[4,5-f]-[1,10]phenanthroline, HL= 2,4-dichlorophenyl acrylic acid) has been synthesized and fully characterized by elemental analysis, IR spectroscopy, UV spectrum, single-crystal X-ray diffraction analysis, luminescence spectra, TGA and powder X-ray diffraction. The structural analysis showed that the complex 1 is a zero dimensional structure with seven coordinated Pb(II) ion. And further, the adjacent complex units are extended into a 2D supramolecular network through the H-bonds [N(4)-H(4)???O(4) and N(7)-H(7)???O(1)]. The luminescence explorations demonstrated that complex 1 has good optical properties. In addition, the quantum chemistry calculations were performed with the Gaussian09 program.
- Chen, Xue,Dun, Linan,Han, Shuang,Li, Chuanbi,Liu, Chunling,Wang, He,Wang, Jiajun,Zhang, Baosheng
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- Toward a Scalable Synthesis and Process for EMA401, Part II: Development and Scale-Up of a Pyridine- A nd Piperidine-Free Knoevenagel-Doebner Condensation
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During route scouting for EMA401 (1), an angiotensin II type 2 antagonist, we identified the synthesis of key amino acid intermediate 2 via its cinnamic acid derivative 3 as a streamlined option. In general, cinnamic acids can be synthesized from the corresponding aldehydes by a Knoevenagel-Doebner condensation in pyridine with piperidine as an organocatalyst. We aimed to replace both of these reagents and found novel conditions involving toluene as the solvent and morpholine as the organocatalyst. Scale-up of the process allowed the production of 25 kg of cinnamic acid 3 that was of the quality required for process development of the subsequent phenylalanine ammonia lyase-catalyzed step. The modified conditions were found to be widely applicable to alternative aldehydes and thus are of relevance to practitioners of chemical scale-up.
- Hardegger, Leo A.,Humair, Roger,Sidler, Eric
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p. 1756 - 1762
(2020/10/26)
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- Cinnamic acid derivative and preparation method and application thereof
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The invention provides a cinnamic acid derivative. The cinnamic acid derivative is of the structure as shown in the formula I. The invention also provides two methods for preparing the cinnamic acid derivative. The two methods depend on a single bond or double bonds in the structure shown in the formula I. The invention further provides a pesticide. The pesticide comprises the cinnamic acid derivative. In addition, the invention provides a sterilization method. The sterilization method includes the step of applying the cinnamic acid derivative or the pesticide to crops. The crops include rice,wheat, fruit trees and vegetables. The low-toxicity, low-residue-content and high-activity environment-friendly cinnamic acid derivative is developed, and the cinnamic acid derivative pesticide can replace traditional high-toxicity and high-residue-content pesticides.
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Paragraph 0114-0116
(2019/10/22)
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- Controlling Plasma Stability of Hydroxamic Acids: A MedChem Toolbox
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Hydroxamic acids are outstanding zinc chelating groups that can be used to design potent and selective metalloenzyme inhibitors in various therapeutic areas. Some hydroxamic acids display a high plasma clearance resulting in poor in vivo activity, though they may be very potent compounds in vitro. We designed a 57-member library of hydroxamic acids to explore the structure-plasma stability relationships in these series and to identify which enzyme(s) and which pharmacophores are critical for plasma stability. Arylesterases and carboxylesterases were identified as the main metabolic enzymes for hydroxamic acids. Finally, we suggest structural features to be introduced or removed to improve stability. This work thus provides the first medicinal chemistry toolbox (experimental procedures and structural guidance) to assess and control the plasma stability of hydroxamic acids and realize their full potential as in vivo pharmacological probes and therapeutic agents. This study is particularly relevant to preclinical development as it allows obtaining compounds equally stable in human and rodent models.
- Hermant, Paul,Bosc, Damien,Piveteau, Catherine,Gealageas, Ronan,Lam, Baovy,Ronco, Cyril,Roignant, Matthieu,Tolojanahary, Hasina,Jean, Ludovic,Renard, Pierre-Yves,Lemdani, Mohamed,Bourotte, Marilyne,Herledan, Adrien,Bedart, Corentin,Biela, Alexandre,Leroux, Florence,Deprez, Benoit,Deprez-Poulain, Rebecca
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supporting information
p. 9067 - 9089
(2017/11/14)
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- Synthesis and antibacterial evaluation of novel 11-O-carbamoyl clarithromycin ketolides
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A series of novel 11-O-carbamoyl clarithromycin ketolides were designed, synthesized and evaluated for their in vitro antibacterial activity. The results showed that the majority of the target compounds displayed improved activity compared with references against erythromycin-resistant S. pneumoniae A22072 expressing the mef gene, S. pneumoniae B1 expressing the erm gene and S. pneumoniae AB11 expressing the mef and erm genes. In particular, compounds 9, 18, 19 and 22 showed the most potent activity against erythromycin-resistant S. pneumoniae A22072 with the MIC values of 0.5?μg/mL. Furthermore, compounds 11, 18, 19, 24 and 29 were also found to exhibit favorable antibacterial activity against erythromycin-susceptible S. pyogenes with the MIC values of 0.125–1?μg/mL, and moderate activity against erythromycin-susceptible S. aureus ATCC25923 and B. subtilis ATCC9372.
- Jia, Li,Yan, Mi,Shen, Yan,Qin, Yinhui,Qiang, Shengsheng,Ma, Shutao
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supporting information
p. 3693 - 3697
(2017/07/27)
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- Telescopic one-pot condensation-hydroamination strategy for the synthesis of optically pure L-phenylalanines from benzaldehydes
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A chemo-enzymatic telescopic approach was designed for the synthesis of L-arylalanines in high yield and optical purity, starting from commercially available and inexpensive substituted benzaldehydes. The method exploits a chemical Knoevenagel–Doebner condensation (optimised to give complete conversions in a short reaction time, employing microwave irradiation) and a biocatalytic phenylalanine ammonia lyase mediated hydroamination (for the stereoselective addition of ammonia). The two reactions can be run sequentially in one pot, bringing together the advantages of chemical and biological catalysis. The preparative applicability was demonstrated with the synthesis of five L-dihalophenylalanines (71–84% yield, 98–99% ee) of relevance as molecular probes, for medicinal chemistry and for the synthesis of pharmaceutical ingredients.
- Parmeggiani, Fabio,Ahmed, Syed T.,Weise, Nicholas J.,Turner, Nicholas J.
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p. 7256 - 7262
(2016/10/26)
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- Design, synthesis and antibacterial activity of cinnamaldehyde derivatives as inhibitors of the bacterial cell division protein FtsZ
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In an attempt to discover potential antibacterial agents against the increasing bacterial resistance, novel cinnamaldehyde derivatives as FtsZ inhibitors were designed, synthesized and evaluated for their antibacterial activity against nine significant pathogens using broth microdilution method, and their cell division inhibitory activity against four representative strains. In the in vitro antibacterial activity, the newly synthesized compounds generally displayed better efficacy against Staphylococcus aureus ATCC25923 than the others. In particular, compounds 3, 8 and 10 exerted superior or comparable activity to all the reference drugs. In the cell division inhibitory activity, all the compounds showed the same trend as their in vitro antibacterial activity, exhibiting better activity against S. aureus ATCC25923 than the other strains. Additionally, compounds 3, 6, 7 and 8 displayed potent cell division inhibitory activity with an MIC value of below 1 1/4g/mL, over 256-fold better than all the reference drugs.
- Li, Xin,Sheng, Juzheng,Huang, Guihua,Ma, Ruixin,Yin, Fengxin,Song, Di,Zhao, Can,Ma, Shutao
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- Synthesis and characterization of two novel biological-based nano organo solid acids with urea moiety and their catalytic applications in the synthesis of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ol), coumarin-3-carboxylic acid and cinnamic acid derivatives under mild and green conditions
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2-Carbamoylhydrazine-1-sulfonic acid and carbamoylsulfamic acid as novel, mild and biological-based nano organocatalysts with urea moiety were designed, synthesized and fully characterized by FT-IR, 1H NMR, 13C NMR, mass spectrometry, elemental analysis, thermal gravimetric, derivative thermal gravimetric, X-ray diffraction patterns, scanning electron microscopy, transmission electron microscopy, energy-dispersive X-ray spectroscopy, atomic force microscopy and UV/Vis analysis. The catalytic applications of 2-carbamoylhydrazine-1-sulfonic acid and carbamoylsulfamic acid were studied in the synthesis of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ol), coumarin-3-carboxylic acid and cinnamic acid derivatives via the condensation reaction between several aromatic aldehydes and 1-phenyl-3-methylpyrazol-5-one (synthesis of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ols)), the Knoevenagel condensation of Meldrum's acid with salicylaldehyde derivatives (synthesis of coumarin-3-carboxylic acids) and the condensation of Meldrum's acid with aromatic aldehydes (synthesis of cinnamic acids) under mild and solvent-free conditions. In the presented studies, some products were formed and reported for the first time. The described nano organo solid acids have potential in industry.
- Zolfigol, Mohammad Ali,Ayazi-Nasrabadi, Roya,Baghery, Saeed
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p. 71942 - 71954
(2015/09/08)
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- Autotaxin inhibitors
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The present invention relates to novel compounds that are autotaxin inhibitors, processes for their preparation, pharmaceutical compositions and medicaments containing them and to their use in diseases and disorders mediated by autotaxin.
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Page/Page column
(2014/06/25)
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- Solvent-dependent regioselective oxidation of trans-chalcones using aqueous hydrogen peroxide
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A novel method for regioselective oxidation of trans-chalcones with hydrogen peroxide in acetonitrile to afford cinnamic acids is reported. Only trans-β-arylacrylic acids were observed. A wide range of functionalized products can be effectively produced from various chalcones in good to excellent yields.
- Wang, Peng,Cai, Jin,Yang, Jiabin,Sun, Chunlong,Li, Lushen,Ji, Min
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p. 518 - 522
(2013/08/25)
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- Design and optimization of quinazoline derivatives as melanin concentrating hormone receptor 1 (MCHR1) antagonists: Part 2
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Melanin concentrating hormone receptor 1 (MCHR1) antagonists have potential for the treatment of obesity and several CNS disorders. In the preceding article, we have described a novel series of quinazolines as MCHR1 antagonists and demonstrated in vivo proof of principle with an early lead. Herein we describe the detailed SAR and SPR studies to identify an optimized lead candidate having good efficacy in a sub-chronic DIO model with a good cardiovascular safety window.
- Sasmal, Sanjita,Balasubrahmanyam,Kanna Reddy, Hariprasada R.,Balaji, Gade,Srinivas, Gujjary,Cheera, Srisailam,Abbineni, Chandrasekhar,Sasmal, Pradip K.,Khanna, Ish,Sebastian,Jadhav, Vikram P.,Singh, Manvendra P.,Talwar, Rashmi,Suresh,Shashikumar, Dhanya,Harinder Reddy,Sihorkar,Frimurer, Thomas M.,Rist, ?ystein,Elster, Lisbeth,H?gberg, Thomas
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p. 3163 - 3167
(2012/06/04)
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- Alum [KA1(S04)2. 12H20]: An efficient, novel, clean, catalyst for Doebner Knoevenagel reaction for the efficient production of αβ-unsaturated acids
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Alum mediated solvent free, microwave enhanced, clean process for the production of -unsaturated acids 3, 5 and 7 is described. Only 10 mole % of alum is enough in this protocol to achieve optimal yields and this protocol is fairly general and applicable to heterocyclic aldehydes and benzopyran 3-aldehydes.
- Suresh, Dhruva Kumar,Sandhu, Jagir S.
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experimental part
p. 1479 - 1483
(2011/12/02)
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- Design, synthesis, and insecticidal activity of 1,5-diphenyl-1-pentanone analogues
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Three series of novel 1,5-diphenyl-1-pentanone derivatives were designed and synthesized. Their structures were characterized by IR, 1H NMR techniques, and elemental analysis. The insecticidal activities of the new compounds were preliminarily evaluated. The bioassay results indicated that the compounds X11-X30 displayed better aphicidal activity against Aphis gossypii than compounds X1-X10 and the lead compound (E)-1,5-diphenyl-1-penten-1-one (A). The inhibitory rates of compounds X6 and X29 were 100% against Plutella xylostella (L.) at 600 mg·L-1. Compounds X12, X13, X19, X24, X25, X26 and X27 showed higher insecticidal activity against Tetranychus cinnabarinus (Boisduval) at 600 mg·L-1 than the lead compound (A).
- Yang, Shaoxiang,Kang, Tieniu,Rui, Changhui,Yang, Xinling,Sun, Yufeng,Cui, Zining,Ling, Yun
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experimental part
p. 2394 - 2400
(2012/02/04)
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- Environmentally benign and energy efficient methodology for condensation: An interesting facet to the classical Perkin reaction
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We have reported use of biodegradable deep eutectic solvent (DES) based on choline chloride and urea, for the synthesis of cinnamic acid and its derivatives via Perkin reaction. The reaction proceeds efficiently under mild condition without use of additional catalyst with better yields. Ease of recovery and reusability of solvent with consistent activity makes this method efficient and environmentally benign. This method is also energy efficient and easy to handle.
- Pawar, Poonam Mahadev,Jarag, Krishna Jagannath,Shankarling, Ganapati Subray
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experimental part
p. 2130 - 2134
(2011/10/03)
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- Synthesis, molecular modeling and biological evaluation of β-ketoacyl-acyl carrier protein synthase III (FabH) as novel antibacterial agents
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A series of novel cinnamic acid secnidazole ester derivatives have been designed and synthesized, and their biological activities were also evaluated as potential inhibitors of FabH. These compounds were assayed for antibacterial activity against Escherichia coli, Pseudomonas aeruginosa, Bacillus subtilis and Staphylococcus aureus. Compounds with potent antibacterial activities were tested for their E. coli FabH inhibitory activity. Compound 3n showed the most potent antibacterial activity with MIC of 1.56-6.25 μg/mL against the tested bacterial strains and exhibited the most potent E. coli FabH inhibitory activity with IC50 of 2.5 μM. Docking simulation was performed to position compound 3n into the E. coli FabH active site to determine the probable binding conformation.
- Zhang, Hong-Jia,Zhu, Di-Di,Li, Zi-Lin,Sun, Juan,Zhu, Hai-Liang
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experimental part
p. 4513 - 4519
(2011/09/12)
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- Bismuth(III) chloride-mediated, efficient, solvent-free, mwi-enhanced doebner condensation for the synthesis of (E)-cinnamic acids
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A bismuth(III) chloride-mediated green process for the production of (E)-cinnamic acid derivatives using microwave irradiation under solvent-free conditions is described. The (E)-cinnamic acids are obtained in excellent yields. This protocol is green because it employs an established environmentally benign procedure, microwave irradiation. Solvent vapor pollution is not there because it is solvent free, and bismuth(III) chloride is an established nontoxic catalyst. Copyright
- Suresh,Kumar, Dhruva,Sandhu, Jagir S.
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experimental part
p. 1915 - 1919
(2010/09/14)
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- Design, synthesis and in vitro antibacterial/antifungal evaluation of novel 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7(1-piperazinyl)quinoline-3-carboxylic acid derivatives
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A series of 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7(1-piperazinyl)quinoline-3-carboxylic acid (norfloxacin) derivatives were prepared according to the principle of combinating bioactive substructures and tested for their activities against five plant pathogenic bacteria and three fungi in vitro. The preliminary bioassays indicated that almost all synthesized target compounds retained the antibacterial activities of norfloxacin and had some antifungal activities as carboxylic acid amide compounds. The activities of compounds 1 and 22 against Xanthomonas oryzae were better than norfloxacin and all tested compounds had better antibacterial activities as compared to the agricultural streptomycin sulfate (a commercial bactericide) against X. oryzae, Xanthomonas axonopodis and Erwinia aroideae. Additionally, compounds 2 and 20 displayed good antifungal activities against Rhizoctonia solani and their inhibition of growth reached 83% and 94% respectively at the concentration of 200 mg/L.
- Yu, Zhiyi,Shi, Guanying,Sun, Qiu,Jin, Hong,Teng, Yun,Tao, Ke,Zhou, Guoping,Liu, Wei,Wen, Fang,Hou, Taiping
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scheme or table
p. 4726 - 4733
(2010/01/06)
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- Synthesis of quaternary salts of ammonia from cinnamic acids and their plant growth retardant activity
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A series of N,N-dimethyl-N-benzyl ammonium chloride cinnamides (1a-e) were prepared from the reaction between cinnamyl chlorides (4a-e) and N,N-dimethylphenylmethanamines (6a-e). These salts were tested for their biological activity on germination, seedling growth and adventitious root formation on hypocotyl cuttings of Vigina radiata (SML-668) and were found to be markedly inhibit germination and seedling growth of mungbean seeds under laboratory conditions.
- Sharma,Kaur, Sukhvir
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p. 612 - 614
(2008/12/20)
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- Synthesis of trans-cinnamic acids from aryl aldehydes and aryl aldehyde bisulfite adducts with malonic acid using piperazine
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Piperazine as a new reagent for the condensation of aryl aldehydes and their bisulfite adducts with malonic acid are described which afford the corresponding cinnamic acids in excellent yields and short reaction times in the absence of solvents under microwave irradiation.
- Khosropour, Ahmad Reza,Khodaei, Mohammad Mehdi,Moghanian, Hassan
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p. 364 - 365
(2007/10/03)
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- Microwave-Assisted Solvent-Free Synthesis of trans-Cinnamic Acids Using Lithium Chloride as Catalyst
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A simple and efficient procedure has been developed for the synthesis of trans-cinnamic acids 3 by the condensation of aromatic aldehydes 1 with malonic acid 2 using LiCl as catalyst under solvent-free conditions using microwave irradiation. The products are obtained in excellent yields and in a state of high purity.
- Mogilaiah,Reddy, G. Randheer
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p. 205 - 210
(2007/10/03)
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- Polyhalogen-substituted cinnamic acids and cinnamic acid derivatives and a process for the preparation of polyhalogen-substituted cinnamic acids and cinnamic acid derivatives
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Polyhalogenated cinnamic acids and cinnamic acid derivatives are prepared by reacting diazonium salts accessible from polyhalogenated anilines with acrylic acid or acrylic acid derivatives in the presence of a homogeneous, palladium-containing catalyst at about ?5 to about +100° C. Some of the cinnamic acids and cinnamic acid derivatives obtainable in this way are new. Cinnamic acids and cinnamic acid derivatives which can be prepared according to the invention can be used for the preparation of indanones which are precursors for agro- and pharmaceutical chemicals and for substances having liquid-crystalline properties.
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- Synthesis of N-[4-(propyl)cyclohexyl]-amides with anti-inflammatory and analgesic activities
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Seventeen (un)substituted N-[4-(propyl)cyclohexyl]-amides (6a-h, 7a-h and 8) were synthesized and tested as anti-inflammatory and analgesic agents. The substituents on the aromatic ring were chosen in order to study the influence of electron-withdrawing or electron-donating residues, that change the electronic density on the aromatic moiety. The pharmacological results allow drawing some preliminary considerations on structure-activity relationships. (C) 2000 Elsevier Science S.A.
- Pau, Amedeo,Boatto, Gianpiero,Asproni, Battistina,Palomba, Michele,Auzzas, Luciana,Cerri, Riccardo,Palagiano, Francesco,Filippelli, Walter,Falcone, Giuseppe,Motola, Giulia
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p. 439 - 447
(2007/10/03)
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- Structure-activity relationship of N-(phenylalkyl)cinnamides as novel NR2B subtype-selective NMDA receptor antagonists
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A novel series of N-(phenylalkyl)cinnamides related to N-(4- phenylbutyl)-3,4-dihydroxy-β-cyanocinnamide (6, an EGFR-K inhibitor with high antiproliferative activity) was synthesized and tested for antagonism at N-methyl-D-aspartate (NMDA) receptor subtypes. Potency and subunit selectivity were assayed by electrical recordings in Xenopus oocytes expressing three binary combinations of cloned rat NMDA receptor subunits: NR1A expressed in combination with either NR2A, NR2B, or NR2C. The N- (phenylalkyl)cinnamides are selective antagonists of NR1(A)/2B receptors. Assayed under steady-state conditions, N-(4-phenylbutyl)-4-hydroxycinnamide (16) has an IC50 value of 77 nM and > 1000-fold selectivity with respect to NR1(A)/2A and NR1(A)/2C receptors. Potency at α1 adrenergic receptors is low for the four cinnamides tested. Inhibition of NR1(A)/2B receptors does not correlate with EGFR and ErbB2/neu tyrosine kinase inhibitor activity. The N-(phenylalkyl)cinnamide series we describe provides a novel and structurally diverse framework for designing new NR2B-selective NMDA antagonists as potential CNS therapeutics.
- Tamiz, Amir P.,Cai, Sui Xiong,Zhou, Zhang-Lin,Yuen, Po-Wai,Schelkun, Robert M.,Whittemore, Edward R.,Weber, Eckard,Woodward, Richard M.,Keana, John F. W.
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p. 3412 - 3420
(2007/10/03)
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- Non solvent reaction: Ammonium acetate catalyzed highly convenient preparation of trans-cinnamic acids
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trans-Cinnamic acids were obtained in near quantitative yield when various aromatic aldehydes were heated with equimolar quantity of malonic acid in presence of ammonium acetate under solvent free conditions. Considerable enhancement in the rate of the reaction was observed when the decarboxylative condensation was carried out under microwave irradiation.
- Sampath Kumar,Subbareddy,Anjaneyulu,Yadav
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p. 3811 - 3815
(2007/10/03)
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- ATP-citrate lyase as a target for hypolipidemic intervention. Design and synthesis of 2-substituted butanedioic acids as novel, potent inhibitors of the enzyme
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ATP-citrate lyase is the primary enzyme responsible for the synthesis of cytosolic acetyl-CoA in many tissues. Inhibitors of the enzyme represent a potentially novel class of hypolipidemic agent, which are anticipated to have combined hypocholesterolemic and hypotriglyceridemic properties. A series of 2-substituted butanedioic acids have been designed and synthesized as inhibitors of the enzyme. The best compounds, 58, 68, 71, 74 have reversible K(i)'s in the 1-3 μM range against the isolated rat enzyme. As representative of this compound class, 58, has been shown to exert its inhibitory action through a mainly competitive mechanism with respect to citrate and a noncompetitive one with respect to CoA. None of the inhibitors were able to inhibit cholesterol and/or fatty acid synthesis in HepG2 cells. This has been attributed to the adverse physicochemical properties of the molecules leading to a lack of cell penetration. Despite this, a lead structural class of compound has been identified with the potential for modification into potent, cell-penetrant, and efficacious inhibitors of ATP- citrate lyase.
- Gribble, Andrew D.,Dolle, Roland E.,Shaw, Antony,McNair, David,Novelli, Riccardo,Novelli, Christine E.,Slingsby, Brian P.,Shah, Virendra P.,Tew, David,Saxty, Barbara A.,Allen, Mark,Groot, Pieter H.,Pearce, Nigel,Yates, John
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p. 3569 - 3584
(2007/10/03)
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- Tha Use of 3,5-Dimethyl-4-nitroisoxazole for the Preparation of α,β-Unsaturated Aromatic Acids
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A series of α,β-unsaturated aromatic acids were preparaed by alkaline hydrolysis of 3-methyl-4-nitro-5-styrylisoxazoles.
- Sarti-Fantoni, P.,Donati, D.,Fiorenza, M.,Moschi, E.,Dal Piaz, V.
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p. 621 - 622
(2007/10/02)
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