771-03-9Relevant academic research and scientific papers
One pot conversion of acetyl chloride to dehydroacetic acid and its coordination in a ruthenium(II) arene complex
Biancalana, Lorenzo,Pampaloni, Guido,Zacchini, Stefano,Marchetti, Fabio
, p. 214 - 221 (2017)
The reaction of [(η6-p-cymene)RuCl(κ2N,O-L-serinate)], 1, with CH3C(O)Cl/NEt3, in chloroform at reflux temperature, led to the serendipitous isolation of the dehydroacetate complex [(η6-p-cymene)RuCl(κ2O,O′-dha)], 2, in low amount. Then, dehydroacetic acid (dhaH) was prepared in one pot by self condensation of acetyl chloride in the presence of NEt3 at room temperature, this reaction being unusual in the landscape of the chemistry of acyl chlorides. Complex 2 was synthesized in 89% yield from [(η6-p-cymene)RuCl2]2 and dhaH, and fully characterized by means of X-ray diffraction, IR and NMR spectroscopy. Complex 2 underwent fast and extensive dissociation of the dehydroacetate ligand in dmso/water solution, the degree of dissociation being substantially higher than that observed for the acetylacetonate ligand from [(η6-p-cymene)RuCl(κ2O,O′-acac)], 3.
Gold-catalyzed homo- And cross-annulation of alkynyl carboxylic acids: a facile access to substituted 4-hydroxy 2: H -pyrones and total synthesis of pseudopyronine A
Choudhary, Shivani,Gayyur,Ghosh, Nayan,Saxena, Anchal
, p. 8716 - 8723 (2020/11/17)
A Au(i)-catalyzed homo- and cross-annulation reaction of alkynyl carboxylic acids offering 3,6-disubstituted 4-hydroxy 2H-pyrones has been demonstrated. The reaction tolerates various substituted alkynyl carboxylic acids and moderate to good yields of α-pyrone scaffolds have been observed. Later, a gram-scale reaction of the acid and the total synthesis of the natural product pseudopyronine A have been carried out successfully.
Process method for producing dehydroacetic acid and patchoulenone and analogues thereof by utilizing carbon dioxide
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, (2019/08/01)
The invention discloses a process method for producing dehydroacetic acid and patchoulenone and analogues thereof by utilizing carbon dioxide. The process method comprises the following steps: weighing a 4-hydroxy-2-pyrone substrate, a cuprous salt and cesium carbonate to be added into a Schleck bottle, degassing, and continuously introducing carbon dioxide; adding a solvent, reacting in an oil bath, and performing after-treatment to obtain a compound 2; carrying out an esterification reaction among the obtained compound 2, (1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride), 2-methylaminopyridine and isopropanol, and performing column chromatography isolation to obtain a compound 3; adding the compound 3 into anhydrous tetrahydrofuran containing sodium hydride, dropping methyl magnesium bromide (or isopentyl magnesium bromide) into the solution, reacting at a normal temperature, and separating, thereby obtaining the dehydroacetic acid or analogue compounds 4 thereof (or patchoulenone and analogue compounds 5 thereof). According to the process method disclosed by the invention, the raw material source is wide, the toxicity is low, and the price is low; the preparation process is simple, the equipment requirement is low, and industrial scale-up production is easily realized.
Synthesis and in vitro evaluation of substituted 3-cinnamoyl-4-hydroxy-pyran-2-one (CHP) in pursuit of new potential antituberculosis agents
Bhat, Zubair Shanib,Ul Lah, Hafiz,Rather, Muzafar Ahmad,Maqbool, Mubashir,Ara, Tabassum,Ahmad, Zahoor,Yousuf, Syed Khalid
supporting information, p. 165 - 172 (2018/02/07)
Tuberculosis is an ever-evolving infectious disease that urgently needs new drugs. In the search for new antituberculosis agents, a library of 3-cinnamoyl-4-hydroxy-6-methyl-2H-pyran-2-ones (CHPs) (2a-2y) was synthesized and evaluated against a standard virulent laboratory strain of Mycobacterium tuberculosis H37Rv. Out of 25 compounds, 11, 5, 7 and 2 (2a and 2u) showed least, moderate, good and appreciable activities, respectively, based on minimum inhibitory concentrations (MICs). Both 2a and 2u exhibited an MIC value of 4 μg ml-1, which was close to those of standard antituberculosis drugs ethambutol, streptomycin and levofloxacin. Neither 2a nor 2u showed any activity against Gram-positive or Gram-negative bacteria and even against non-tuberculous mycobacterium, i.e. Mycobacterium smegmatis. Thus, like the antituberculosis drugs rifampicin, isoniazid and pretomanid, they are highly TB specific. All the pyrone-based chalcones showed no recognizable level of cytotoxicity against normal human kidney cell line (HEK-293) up to 80 μM concentration and 11 exhibited an IC50 ≤ 100 μM (highest tested concentration). On further investigation, both 2a and 2u proved to be nontoxic against four human cell lines but 2a proved to be a better choice as it did not reach IC50 even at 100 μM (highest tested concentration) while the IC50 of 2u was around 80 μM. In conclusion, our results demonstrate that 2a is specific against M. tuberculosis with no appreciable toxicity; its activity matches that of some clinically approved antituberculosis drugs and it therefore merits further evaluation.
Isolation of the antibiotic pseudopyronine B and SAR evaluation of C3/C6 alkyl analogs
Bouthillette, Leah M.,Darcey, Catherine A.,Handy, Tess E.,Seaton, Sarah C.,Wolfe, Amanda L.
supporting information, p. 2762 - 2765 (2017/05/29)
Natural products are an abundant source of structurally diverse compounds with antibacterial activity that can be used to develop new and potent antibiotics. One such class of natural products is the pseudopyronines. Here we present the isolation of pseudopyronine B (2) from a Pseudomonas species found in garden soil in Western North Carolina, and SAR evaluation of C3 and C6 alkyl analogs of the natural product for antibacterial activity against Gram-positive and Gram-negative bacteria. We found a direct relationship between antibacterial activity and C3/C6 alkyl chain length. For inhibition of Gram-positive bacteria, alkyl chain lengths between 6 and 7 carbons were found to be the most active (IC50?=?0.04–3.8?μg/mL) whereas short alkyl chain analogs showed modest activity against Gram-negative bacteria (IC50?=?223–304?μg/mL). This demonstrates the potential for this class of natural products to be optimized for selective activity against either Gram-positive or Gram-negative bacteria.
A rhodamine embedded bio-compatible smart molecule mimicking a combinatorial logic circuit and 'key-pad lock' memory device for defending against information risk
Mistri, Tarun,Alam, Rabiul,Bhowmick, Rahul,Katarkar, Atul,Chaudhuri, Keya,Ali, Mahammad
, p. 330 - 339 (2016/01/12)
Organic molecules with the possibility of logic operations are highly useful building blocks for the development of molecule-based "intelligent" devices for information processing applications. We have designed herein a very simple bio-friendly chemosensor (LC) equipped with a rhodamine fluorophore moiety. This probe showed a chromo-fluorescence response profile for Al3+ but a colorimetric response for Cu2+ metal. The absorption responses of LC caused by these metal ions along with the "OFF-ON-OFF" fluorescence behavior of an LC-Al3+ complex towards EDTA were employed for the development of a three-input and one output combinatorial molecular system. Interactions of the mentioned metal ions with LC in controlled sequential experiments gave fluorescence responses, enabling us to fabricate a 'key-pad-logic' function. So, a single molecular system performing such multiple 'Boolean' operations not only simplifies the complexity of a chemical driven 'Intelligence' device but also enriches the security of such a device against information invasion due to the sequence controlled sensor-analyte interactions and may find potential applications in biocompatible molecular logic platforms.
Potassium fluoride-barium oxide catalysis in an easy and efficient synthesis of methysticin from piperonal under microwave irradiation
Benferrah,Hammadi,Berthiol
, p. 1939 - 1944 (2015/10/12)
Condensation of compounds containing active methylene group with aromatic aldehyde (piperonal) in the presence of BaO on KF without a solvent under microwave irradiation is an efficient synthetic approach to methysticin and derivatives of kavalactones (4-methoxy-6-styryl-pyran-2-ones).
Structural basis for the formation of acylalkylpyrones from two β-ketoacyl units by the fungal type III polyketide synthase CsyB
Mori, Takahiro,Yang, Dengfeng,Matsui, Takashi,Hashimoto, Makoto,Morita, Hiroyuki,Fujii, Isao,Abe, Ikuro
, p. 5214 - 5225 (2015/06/11)
Background: CsyB from Aspergillus oryzae catalyzes the condensation of two β-ketoacyl units.
Synthesis and bioevaluation of a series of α-pyrone derivatives as potent activators of Nrf2/ARE pathway (part I)
Xi, Mei-Yang,Sun, Zhong-Ying,Sun, Hao-Peng,Jia, Jian-Min,Jiang, Zheng-Yu,Tao, Lei,Ye, Ming,Yang, Xi,Wang, Ya-Jing,Xue, Xin,Huang, Jing-Jie,Gao, Yuan,Guo, Xiao-Ke,Zhang, Sheng-Lie,Yang, Ying-Rui,Guo, Qing-Long,Hu, Rong,You, Qi-Dong
, p. 364 - 371 (2013/10/01)
When exposed to electrophiles, human colorectal cancer cells (HCT116) counteract oxidative stress through activating NF-E2-related factor 2 (Nrf2)/antioxidant response element (ARE) pathway. To identify new activators, luciferase reporter gene assay was used to screen in-house database of our laboratory, leading to a novel α-pyrone compound 1 as a hit. 2 with 2-fluoro phenyl group exhibited the strongest ARE inductive activity in the first round structure-activity relationship (SAR) study. Biological studies showed the compound induced nuclear translocation of Nrf2 preceded by phosphorylation of ERK1/2. The data encouraged us to use 2 as lead and 20 derivatives were synthesized to discuss a more detailed SAR, leading to a more potent compound 9, which can be the starting compound for further modification.
Regeneration of the carbonyl group in the hypervalent iodine oxidation of carbonyl derivatives of dehydroacetic acid and its analogues
Pundeer, Rashmi,Chaudhri, Vishwas,Kinger, Mayank,Prakash, Om
, p. 834 - 837 (2008/09/18)
Hypervalent iodine oxidation of carbonyl derivatives of dehydroacetic acid and its analogues leads to a mild and efficient regeneration of parent carbonyl compounds leaving pyrone moiety intact.
