- Carane amino alcohols as organocatalysts in asymmetric aldol reaction of isatin with acetone
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Carane-derived β-amino alcohols with amino and hydroxy groups at positions 3 and 4 differing in their mutual arrangement and configuration were synthesized. Their application as organocatalysts in the asymmetric aldol reaction of isatin with acetone allowed one to obtain adducts with up to 84% enantiomeric excess.
- Banina,Sudarikov,Nigmatov,Frolova,Slepukhin,Zlotin,Kutchin
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- Anti-inflammatory properties of convolutamydine A and two structural analogues
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Aims: Convolutamydine A is an oxindole alkaloid that can be isolated from a marine bryozoan. Due to the variety of biological effects, two analogues were synthesized and their anti-inflammatory properties were evaluated. Main methods: The anti-inflammatory effects of convolutamydine A and its analogues (ISA003 and ISA147) were investigated in a formalin-induced licking behaviour model, where mice received an intraplantar injection of formalin and their licking behaviour was evaluated for 30 min. Additionally, inflammatory parameters were evaluated in a subcutaneous air pouch (SAP) model of carrageenan-induced inflammation. Exudates were collected for leukocyte counts; measurement of protein, prostaglandin E2 (PGE2) and cytokines by ELISA; and analysis of nitric oxide (NO) using a nitrate conversion protocol. Cyclooxygenase-2 (COX2) and inducible nitric oxide synthase (iNOS) from RAW 264.7 cells were quantified by immunoblotting. Key findings: Convolutamydine A and its two analogues inhibited the formalin-induced licking response at doses as low as 0.01 mg/kg. An inhibitory effect was also observed on leukocyte migration and the production of NO, PGE2 and cytokines (IL-6 and TNF-α). The reduction in inflammatory parameters did not appear to be correlated with a direct reduction in the number of cells in the SAP, because a reduction in NO and PGE2 production by cultured macrophages was observed in addition to the inhibition of iNOS and COX2 enzyme expression. Significance: These results indicate that convolutamydine A and its two analogues have significant anti-inflammatory effects. These substances can be improved to generate lead compounds for the synthesis of new anti-inflammatory drugs.
- Fernandes, Patricia D.,Zardo, Renata S.,Figueiredo, Gabriella S.M.,Silva, Brbara V.,Pinto, Angelo C.
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- Convolutamydine A and synthetic analogues have antinociceptive properties in mice
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Convolutamydine A, an oxindole that originated from a marine bryozoan, has several biological effects. In this study, we aimed to investigate the antinociceptive effects of convolutamydine A and two new synthetic analogues. Convolutamydine A and the two analogues were given orally to assess their ability to induce antinociceptive effects. Formalin-induced licking response, acetic acid-induced contortions, and hot plate models were used to characterize the effects of convolutamydine A and its analogues. Convolutamydine A (4,6-bromo-3-(2-oxopropyl)-3-hydroxy-2-oxindole), compound 1 (3-(2-oxopropyl)-3-hydroxy-2-oxindole), and compound 2 (5-bromo-3-(2-oxopropyl)- 3-hydroxy-2-oxindole) caused peripheral antinociceptive and anti-inflammatory effects in the acetic acid-induced contortions and the formalin-induced licking models. Supraspinal effects were also observed in the hot plate model and were similar to those obtained with morphine. The peripheral effects were not mediated by the cholinergic or opioid systems. The antinociceptive effects of convolutamydine A seem to be mediated by all three systems (cholinergic, opioid, and nitric oxide systems), and the mechanism of action of compounds 1 and 2 involved cholinergic and nitric oxide-mediated mechanisms. Convolutamydine A and its analogues (compounds 1 and 2) showed good antinociceptive ability after systemic administration in acute pain models. The antinociceptive action mediated by cholinergic, opioid, and nitric oxide systems could explain why convolutamydine A, compound 1, and compound 2 retained their antinociceptive effects. The doses used were similar to the doses of morphine and were much lower than that of acetylsalicylic acid, the classical analgesic and anti-inflammatory drug. In conclusion, convolutamydine A and the two analogues demonstrated antinociceptive effects comparable to morphine's effects.
- Figueiredo, Gabriela S.M.,Zardo, Renata S.,Silva, Barbara V.,Violante, Flavio A.,Pinto, Angelo C.,Fernandes, Patricia D.
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- Copper(II) Triflate Catalyzed Regioselective and Enantioselective Propargylation of Isatin Derivatives by Using Allenylboronic Acid Pinacol Ester
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We report a simple protocol for the synthesis of homopropargyl alcohols with isatin derivatives under milder conditions for the first time. The excellent regioselectivity and yields were observed with copper triflate as a Lewis-acid catalyst and allenylboronic acid pinacol ester as a nucleophile in aqueous media. A gram-scale synthesis was done to check the efficiency of the protocol with retention in selectivity. Further one-step functionalization of these homopropargyl alcohols was established as the synthetic application of these alkynes. The enantioselective synthesis of these chiral propargyl alcohols has also been explored for the first time with an enantiomeric ratio up to 12:88.
- Gupta, Naveen,Tak, Rajkumar,Nazish, Mohd,Jakhar, Ajay,Khan, Noor-ul H.,Kureshy, Rukhsana I.
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- Control of Chemical Reactions by Using Molecules that Buffer Non-aqueous Solutions
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Control of chemical reactions is necessary to obtain designer chemical transformation products and for preventing decomposition and isomerization reactions of compounds of interest. For the control of chemical events in aqueous solutions, the use of aqueo
- Sohail, Muhammad,Tanaka, Fujie
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- Asymmetric aldol reaction of isatins with acetone in the presence of terpene amino alcohols
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Asymmetric aldol reactions of isatin and 4,6-dibromoisatin with acetone are efficiently catalyzed by β-amino alcohols derived from α-pinene and 3-carene. The target compounds can be isolated by crystallization from toluene, which eliminates the need for using chromatography and makes the asymmetric synthesis of (R)-convolutamydine A (up to 94% ee and yield 75%) simple and convenient.
- Banina, Olga A.,Frolova, Larisa L.,Kutchin, Alexander V.,Nigmatov, Albert G.,Sudarikov, Denis V.,Zlotin, Sergei G.
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- Cu(II)-thiophene-2,5-bis(amino-alcohol) mediated asymmetric Aldol reaction and Domino Knoevenagel Michael cyclization: A new highly efficient Lewis acid catalyst
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The highly efficient Lewis acid-catalytic system Cu(II)-thiophene-2,5-bis(amino-alcohol) has been developed for enantioselective Aldol reaction of isatin derivatives with ketones. The new catalytic system also proved to be highly enantioselective for the one pot three-component Domino Knoevenagel Michael cyclization reaction of substituted isatin with malononitrile and ethylacetoacetate. The chiral ligand (2S,20S)-2,20-((thiophene-2,5-diylbis(methylene))bis(azanediyl))bis(3-phenylpropan-1-ol) (L1) in combination with Cu(OAc)2Η2O employed as a new Lewis acid catalyst, furnished 3-substituted-3- hydroxyindolin-2-ones derivatives (3a-s) in good to excellent yields (81-99%) with high enantioselectivities (up to 96% ee) and spiro[4H-pyran-3,3-oxindole] derivatives (6a-l) in excellent yields (89-99%) with high ee (up to 95%). These aldol products and spiro-oxindoles constitute a core structural motif in a large number of pharmaceutically active molecules and natural products.
- Al-Majid, Abdullah Mohammed,Alammari, Abdullah Saleh,Alshahrani, Saeed,Barakat, Assem,Haukka, Matti,Islam, Mohammad Shahidul
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p. 6149 - 6165
(2022/03/31)
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- MS 4A-PROMOTED AQUEOUS PHOSPHO-ALDOL-BROOK REARRANGEMENT REACTION of ISATINS
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An efficient, simple, environment-friendly, and low-cost protocol for the hydrophosphonation of isatins using inexpensive and non-toxic MS 4A as a recyclable additive in water has been developed. This protocol is also suitable for the aldol reaction of is
- Han, Wei,Liu, Fan,Oriyama, Takeshi
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p. 159 - 166
(2022/01/08)
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- Kinetic Resolution of Tertiary Alcohols by Chiral DMAP Derivatives: Enantioselective Access to 3-Hydroxy-3-substituted 2-Oxindoles
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We developed an efficient acylative kinetic resolution of 3-hydroxy-3-substituted 2-oxindoles by a chiral DMAP derivative having a 1,1′-binaphthyl with two tert-alcohols units. A wide range of 3-hydroxy-3-substituted oxindoles having various functional groups were efficiently resolved (14 examples, up to s = 60) in the presence of 1 mol % of catalyst within 3-9 h. Multigram-scale reactions (10 g) also proceeded with a high s-factor (s = 43) within 5 h.
- Fujii, Kazuki,Mandai, Hiroki,Mitsudo, Koichi,Shiomoto, Ryuhei,Suga, Seiji
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supporting information
p. 1169 - 1174
(2021/01/13)
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- Oxidative ring expansion of 3-hydroxy-3-phenacyloxindoles using phenyliodine diacetate and molecular iodine: Synthesis of 2-hydroxy-2-aryl/alkyl-2,3-dihydroquinolin-4(1H)-ones
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Oxidation of tertiary alcohol of the type 3-hydroxy-3-phenacyloxindoles using the combination of phenyliodine diacetate and molecular iodine in methanol results in oxidative cleavage of C2-C3 bond to form isocyanate as an intermediate with its subsequent
- Kavale, Ashish C.,Kalbandhe, Amit H.,Opai, Imran A.,Jichkar, Atul A.,Karade, Nandkishor N.
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supporting information
(2020/12/14)
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- A Continuous-Flow Route to Enantioenriched 3-Substituted-3-Hydroxyoxindoles: Organocatalytic Aldol Reactions of Isatin with Acetone
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An efficient L-leucinol catalysed asymmetric synthesis of 3-substitued-3-hydroxyoxindoles was for the first time completed under continuous flow, providing a safer route for accelerating the reaction at higher temperatures without adversely affecting enan
- Tseke, Kavnen,Lennon, Claire,O'Mahony, Joseph,Kinsella, Michael
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p. 5767 - 5774
(2021/09/18)
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- Ultrasonication-Assisted Synthesis of a d-Glucosamine-Based β-CD Inclusion Complex and Its Application as an Aqueous Heterogeneous Organocatalytic System
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For the first time, an inclusion complex has been crafted between a carbohydrate-based molecule and a β-cyclodextrin (CD) hydrophobic cavity for asymmetric catalytic applications. This novel d-glucosamine-based inclusion compound has been synthesized in h
- Rani, Dhiraj,Sethi, Aaftaab,Kaur, Khushwinder,Agarwal, Jyoti
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p. 9548 - 9557
(2020/09/09)
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- Mapping the Surface Groups of Amine-Rich Carbon Dots Enables Covalent Catalysis in Aqueous Media
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Carbon nanodots stand as the missing link between the molecular and the nanoscale world, owing to the unique molecular-like behavior emerging from their synthetic precursors. A converging set of analytical and spectroscopic data yields a precise inventory
- Amato, Francesco,Bonchio, Marcella,Companyó, Xavier,Dell'Amico, Luca,Filippini, Giacomo,Prato, Maurizio,Ragazzon, Giulio,Rosso, Cristian,Vega-Pe?aloza, Alberto
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supporting information
p. 3022 - 3037
(2020/11/03)
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- Glucose-containing imidazolium salt-catalyzed cross-aldol reaction of isatins and unactivated ketones
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Ketone–ketone cross-aldol reaction of isatins and unactivated ketones was catalyzed by glucose-containing imidazolium salt β-1-imidazole-2,3,4,6-tetra-o-hydroxy-d-glucopyranosyl bromide in neutral condition to generate 3-alkyl-3-hydroxyindolin-2-ones in e
- Wan, Yu,Yuan, Rui,Cui, Hao,Zhang, Xiao-xiao,Li, Ming-qi,Xu, Jiang-biao,Dou, Peng-fei,Zhang, Long-yan,Wu, Hui
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p. 2561 - 2570
(2018/02/16)
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- Bromo β - 1 - imidazole - 2, 3, 4, 6 - tetrahydroxy - D - pyran glucose synthesis and use (by machine translation)
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A bromo β - 1 - imidazole - 2, 3, 4, 6 - tetrahydroxy - D - pyran glucose synthesis and use, which belongs to the multi-component reaction chemical synthesis pyran glucose and use thereof. Bromo β - 1 - imidazole - 2, 3, 4, 6 - tetrahydroxy - D - pyran gl
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Paragraph 0044; 0045; 0046; 0047; 0048-0050; 0053-0056
(2017/07/04)
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- Towards a Series of Chiral Primary Amines Bearing α-Amino Acid and Benzo[d]imidazole Pendants, and Their Application in Asymmetric Aldol Reactions
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A straightforward reaction path towards chiral primary amines bearing α-amino acid and benzo[d]imidazole pendants has been developed. Six starting essential α-amino acids were converted into the target chiral amines in a four-step synthesis. The prepared
- Mohite, Pravinkumar Hansraj,Drabina, Pavel,Bure?, Filip
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p. 1613 - 1622
(2017/03/21)
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- C U 2O-Catalyzed C(SP 3)-H/C(SP 3)-H Cross-Coupling Using TEMPO: Synthesis of 3-(2-Oxoalkyl)-3-hydroxyoxindoles
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A simple, convenient, and efficient oxidative cross-coupling reaction of oxindoles with ketones toward a variety of 3-(2-oxoalkyl)-3-hydroxyoxindoles in moderate to excellent yields has been developed. This transformation proceeds via a tandem oxidative cross-coupling by using 2,2,6,6-tetramethylpiperidine N-oxyl (TEMPO) in air as an environmentally benign oxidant. This methodology provides an alternative approach for the direct generation of all-carbon quaternary centers at the C3 position of oxindoles.
- Wang, Baoshuang,Zhu, Jiayi,Wei, Yang,Luo, Guotian,Qu, Hongen,Liu, Liang-Xian
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p. 2841 - 2848
(2015/12/23)
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- Ordered short channel mesoporous silica modified with 1,3,5-triazine-piperazine as a versatile recyclable basic catalyst for cross-aldol, Knoevenagel and conjugate addition reactions with isatins
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A triazine-piperazine immobilized on ordered short channel mesoporous silica was synthesized, characterized and used as a heterogeneous basic catalyst in the synthesis of indole skeletal structures from isatin derivatives under ambient reaction conditions in good to excellent isolated yields. The catalyst showed no loss in its efficacy over 10 recycle experiments. This journal is
- Gupta, Naveen,Roy, Tamal,Ghosh, Debashis,Abdi, Sayed H. R.,Kureshy, Rukhsana I.,Khan, Noor-Ul H.,Bajaj, Hari C.
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p. 17843 - 17850
(2015/03/04)
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- Natural amino acid salt catalyzed aldol reactions of isatins with ketones: highly enantioselective construction of 3-alkyl-3-hydroxyindolin-2-ones
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Abstract The asymmetric synthesis of 3-alkyl-3-hydroxyindolin-2-ones via direct aldol reaction of isatin with ketones catalyzed by natural amino acid salts is described, in which the phenylalanine lithium salt was found to be the best catalyst. This strategy was then applied to a variety of isatin and ketone substrates and the corresponding aldol products were obtained in excellent yields (up to 97%) with good to excellent enantioselectivities (up to 90%).
- Chen, Gong,Ju, Yuan,Yang, Tao,Li, Zicheng,Ang, Wei,Sang, Zitai,Liu, Jie,Luo, Youfu
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p. 943 - 947
(2015/09/01)
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- Synthesis of functionalized 2-oxindoles by Friedel-Crafts reactions
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A series of acetonyl-substituted 3-hydroxy-2-oxindoles have been prepared and reacted with arenes in superacid promoted Friedel-Crafts reactions. The product aryl-substituted 2-oxindoles are formed in generally good yields. With substituted arenes such as
- Gasonoo, Makafui,Klumpp, Douglas A.
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p. 4737 - 4739
(2015/07/20)
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- Primary-tertiary diamine-catalyzed Michael addition of ketones to isatylidenemalononitrile derivatives
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Simple primary-tertiary diamines easily derived from natural primary amino acids were used to catalyze the Michael addition of ketones with isatylidenemalononitrile derivatives. Diamine 1a in combination with D-CSA as an additive provided Michael adducts
- Kumar, Akshay,Chimni, Swapandeep Singh
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supporting information
p. 929 - 935
(2014/05/20)
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- Molecular sieve mediated decarboxylative Mannich and aldol reactions of β-ketoacids
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A molecular sieve mediated decarboxylative Mannich reaction of β-ketoacids with sulfonyl imines is reported; this protocol leads to an efficient preparation of synthetically useful β-amino ketones. An analogous molecular sieve promoted decarboxylative aldol reaction between β-ketoacids and isatins is also described, which affords bioactive 3-substituted-3-hydroxy-oxindoles in excellent yields.
- Zhong, Fangrui,Jiang, Chunhui,Yao, Weijun,Xu, Li-Wen,Lu, Yixin
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supporting information
p. 4333 - 4336
(2013/07/26)
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- Organocatalyzed direct asymmetric aldol reaction of isatins in water: Low catalyst loading in command
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Simple primary-tertiary diamines easily derived from natural primary amino acids have been used to catalyze the aldol reactions in water. The 1 mol % of diamine catalyst is sufficient to catalyze the aldol reaction of cyclohexanone/acetone to isatins prov
- Kumar, Akshay,Chimni, Swapandeep Singh
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p. 5197 - 5204
(2013/06/27)
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- Quinidine thiourea-catalyzed aldol reaction of unactivated ketones: Highly enantioselective synthesis of 3-alkyl-3-hydroxyindolin-2-ones
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New catalysis mechanism! The asymmetric aldol reaction of unactivated ketones and activated carbonyl compounds is realized with a quinidine-derived thiourea catalyst (see scheme), and involves an enolate mechanism instead of the widely used enamine mechan
- Guo, Qunsheng,Bhanushali, Mayur,Zhao, Cong-Gui
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scheme or table
p. 9460 - 9464
(2011/02/22)
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- Catalyst-free aldol condensation of ketones and isatins under mild reaction conditions in DMF with molecular sieves 4 A as additive
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In the presence of molecular sieve (MS) 4 A in DMF, a catalyst-free aldol condensation of a variety of aromatic and aliphatic ketones with isatins under mild reaction conditions has been developed. This approach may provide access to a wide range of 3-sub
- Chen, Wen-Bing,Liao, Yu-Hua,Du, Xi-Lin,Zhang, Xiao-Mei,Yuan, Wei-Cheng
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experimental part
p. 1465 - 1476
(2010/05/18)
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- Catalytic enantioselective fluorination of oxindoles
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We have developed a highly efficient catalytic enantioselective fluorination of oxindole derivatives. In the presence of a catalytic amount of chiral Pd complex 2 (2.5 mol %), various substrates, including aryl- and alkyl-substituted oxindoles, were fluor
- Hamashima, Yoshitaka,Suzuki, Toshiaki,Takano, Hisashi,Shimura, Yuta,Sodeoka, Mikiko
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p. 10164 - 10165
(2007/10/03)
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- Synthesis of 3-hydroxyindolin-2-one alkaloids, (±)-donaxaridine and (±)-convolutamydines A and E, through enolization-Claisen rearrangement of 2-allyloxyindolin-3-ones
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Claisen rearrangement triggered by enolization of 2-allyloxyindolin-3-ones with DBU was performed in order to prepare 3-allyl-3-hydroxyindolin-2-ones. Total synthesis of 3-hydroxyindolin-2-one alkaloids, (±)-donaxaridine, as well as (±)-convolutamydines A
- Kawasaki, Tomomi,Nagaoka, Miyuki,Satoh, Tomoko,Okamoto, Ayako,Ukon, Rie,Ogawa, Atsuyo
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p. 3493 - 3503
(2007/10/03)
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- A versatile synthetic methodology for the synthesis of tryptophols
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Tryptophols have been obtained in high yields by the reduction of 3-substituted-dioxindoles (obtained by the aldol condensation reaction of ketones with isatins or by a modified Knovenagel malonate condensation) using a borane tetrahydrofuran complex. The reported methodology offers distinct advantages over existing methods for the synthesis of these compounds, including consistently greater yields, diastereoselective syntheses and the possibility for the synthesis of a wide range of structurally different tryptophols. The reduction reaction was found to proceed via an intermediate 1,3-diol-oxindole, which was obtained diastereoselectively and, which was subsequently reduced to the corresponding tryptophol.
- Garden, Simon J,Da Silva, Rosangela B,Pinto, Angelo C
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p. 8399 - 8412
(2007/10/03)
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- Synthesis of potential anticonvulsants: Condensation of isatins with acetone and related ketones
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Substituted isatins were condensed with acetone and other ketones to give analogs of 3-hydroxy-3-acetonyloxindole. Some of these alcohols were dehydrated. Several compounds with anticonvulsant activity were obtained.
- Popp,Parson,Donigan
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p. 1235 - 1237
(2007/10/02)
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