cas 60434-13-1, 5-chloro-1-methyl-1H-indole-2,3-dione

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New spiroindolinones bearing 5-chlorobenzothiazole moiety
In this study, 5-chloro-3H-spiro-[1,3-benzothiazole-2,3'-indole]-2'(1'H)-one derivatives 3a-l were synthesized by the reaction of 1H-indole-2,3-diones 1a-l with 2-amino-4-chlorothiophenol 2 in ethanol. 3a-l were tested for their abilities to inhibit lipid peroxidation (LP), scavenge DPPH? and ABTS?+ radicals, and to reduce Fe3+ to Fe2+. Most of the tested compounds exhibited potent scavenging activities against ABTS?+ radical, reducing powers and strong inhibitory capacity on LP. 3a, 3d, 3e, 3h, 3j and 3k chosen as prototypes were evaluated in the National Cancer Institute's in vitro primary anticancer assay. The greatest growth inhibitions were observed against a non-small cell lung cancer cell line HOP-92 for R1-fluoro substituted 3d and a renal cancer cell line RXF-393 for R-chloro substituted 3e in the primary screen.
Ermut, G?rkem,Karali, Nilgün,?zsoy, Nurten,Can, Ay?e
p. 457 - 468
(2014)
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Base-mediated allylation of N-2,2,2-trifluoroethylisatin ketimines and its application in aza-Prins reactions
The aza-Prins reaction of allylic imines triggered by N-2,2,2-trifluoroethylisatin ketimine is accomplished for the synthesis of spirooxindole derivatives involving trifluoromethyl group in the presence of TMSX. This cyclization reaction is operationally simple and proceeds under mild conditions using non-toxic reagents. Notably, while the previous our work could not be compatible with TMSX (X = Cl, I, etc) in one-pot process, this work describes successful aza-Prins reaction with TMSX (X = Cl, I, etc) via step-by-step process.
Kim, Jaehwan,Yeon Park, Se,Jung, Myeongjin,Jang, Woo Cheol,Ko, Haye Min
supporting information

(2021/12/01)

Decarboxylative Organocatalyzed Addition Reactions of Fluoroacetate Surrogates for the Synthesis of Fluorinated Oxindoles
Fluorinated malonic acid half thioesters (F-MAHTs) were used as thioester enolate equivalents in organocatalyzed addition reactions to isatins. The products from a range of different N-protected and nonprotected isatins were obtained under mild reaction conditions in high yields and enantioselectivities. The unique reactivity of the thioester moiety enabled diverse derivatization and allowed for the straightforward access to a fluorinated analogue of the anticancer agent (S)-YK-4-279, a therapeutically active compound against Ewing's sarcoma.
Zetschok, Dominik,Heieck, Lukas,Wennemers, Helma
supporting information
p. 1753 - 1757
(2021/03/08)

Organocatalytic Asymmetric Synthesis of Aza-Spirooxindoles via Michael/Friedel-Crafts Cascade Reaction of 1,3-Nitroenynes and 3-Pyrrolyloxindoles
An asymmetric [3+3] cyclization of nitroenynes and 3-pyrrolyloxindoles has been realized with a chiral bifunctional squaramide catalyst. This Michael/Friedel-Crafts cascade strategy provides a facile and efficient access to enantioenriched polycyclic aza-spirooxindoles with 32-95% isolated yields and excellent stereocontrol under mild reaction conditions.
Ni, Qijian,Wang, Xuyang,Zeng, Da,Wu, Qianling,Song, Xiaoxiao
supporting information
p. 2273 - 2278
(2021/04/05)

Construction of 2-alkynyl aza-spiro[4,5]indole scaffolds: Via sequential C-H activations for modular click chemistry libraries
Herein, we have developed a strategy of sequential C-H activations of indole to construct novel 2-alkynyl aza-spiro[4,5]indole scaffolds, which incorporated both alkyne and spiro-units into indole. Gram-scale synthesis and a one-pot, three-step synthesis demonstrated the utility of this protocol. Hybrid conjugates with an oseltamivir derivative further offered a powerful tool for the construction of a versatile spiroindole-containing library via click chemistry. This journal is
Zhang, Jun,Wang, Mengmeng,Wang, Huiying,Xu, Hui,Chen, Junjie,Guo, Ziqiong,Ma, Biao,Ban, Shu-Rong,Dai, Hui-Xiong
supporting information
p. 8656 - 8659
(2021/09/04)

3-Carboxamide oxindoles as 1,3-C,N-bisnucleophiles for the highly diastereoselective synthesis of CF3-containing spiro-δ-lactam oxindoles featuring acyl at the ortho-position of spiro carbon atom
A simple and efficient strategy has been established for the synthesis of δ-lactam fused oxindoles via the Michael/N-hemiketalization cascade reaction of 3-carboxamide oxindoles and α,β-unsaturated trifluoromethyl ketones. A wide range of structurally novel CF3-containing spiro-δ-lactam oxindoles featuring acyl at the ortho-position of spiro carbon atoms were obtained in moderate to good yields with excellent diastereoselectivities under mild conditions. This work represents the first example of a systematic study of 3-carboxamide oxindoles as 1,3-C,N bisnucleophiles.
Zhao, Hongcai,Zhang, Zhengbing,Lu, Wenhua,Han, Pan,Wang, Wei,Jing, Linhai
supporting information

(2021/10/01)

Synthesis, characterization and anticancer activity of (5,1-substituted)-3-(indoline-4-(thiophene- 2-yl-methylene)-2-(p-tolyl)-2-methylene)-4,3-dihydro-1h-imidazole-5-one derivatives
The synthesis of novel imidazole-5-one derivatives (5a-j) was allowed in a conventional method by way of Erlenmeyer and Schiff base mechanism. Compound 2a was synthesized by Erlenmeyer reaction of N-(4-methoxy benzoyl)glycine with 2-thiophene-carboxaldehyde in the presence of acetic anhydride and anhydrous sodium acetate. Finally, it undergoes dehydration reaction with Schiff bases of isatin derivatives (4a-j) to yield final compounds 5a-j. The organic potentials of the newly synthesized imidazole-5-one derivatives have been evaluated for their in vitro anticancer activity by MTT assay method. It against MCF-7 cells as comparison with doxorubicin popular drug. The synthesized compounds 5e, 5f and 5j exhibited excellent anticancer activity against MCF-7 cell lines.
BAYYA, CHANDRAPRAKASH,MANDA, SARANGAPANI
p. 2027 - 2032
(2021/08/24)

Bismuth(iii)-catalyzed regioselective alkylation of tetrahydroquinolines and indolines towards the synthesis of bioactive core-biaryl oxindoles and CYP19 inhibitors
Bismuth(iii)-catalyzed regioselective functionalization at the C-6 position of tetrahydroquinolines and the C-5 position of indolines has been demonstrated. For the first time, one pot symmetrical and unsymmetrical arylation of isatins with tetrahydroquinolines was accomplished giving a completely new product skeleton in good to excellent yields. Most importantly, this protocol leads to the formation of a highly strained quaternary carbon stereogenic center, which is a challenging task. Benzhydryl and 1-phenylethyl trichloroacetimidates have been used as the alkylating partners to functionalize the C-6 and C-5 positions of tetrahydroquinolines and indolines, respectively. The scope of the developed methodology has been extended for the synthesis of the bioactive CYP19-inhibitor and its analogue.
Prusty, Namrata,Kinthada, Lakshmana K.,Meena, Rohit,Chebolu, Rajesh,Ravikumar, Ponneri Chandrababu
p. 891 - 905
(2021/02/09)

Design, synthesis, and biological evaluation of 1,2,3-triazole-linked triazino[5,6-b]indole-benzene sulfonamide conjugates as potent carbonic anhydrase I, II, IX, and XIII inhibitors
A series of 1,2,3-triazole-linked triazino[5,6-b]indole-benzene sulfonamide hybrids (6a– 6o) was synthesized and evaluated for carbonic anhydrase (CA, EC 4.2.1.1) inhibitory activity against the human (h) isoforms hCA I, II, XIII (cytosolic isoforms), and hCA IX (transmembrane tumor-associated isoform). The results revealed that the compounds 6a–6o exhibited Ki values in the low to medium nanomolar range against hCA II and hCA IX (Kis ranging from 7.7 nM to 41.3 nM) and higher Ki values against hCA I and hCA XIII. Compound 6i showed potent inhibition of hCA II (Ki = 7.7nM), being more effective compared to the standard inhibitor acetazolamide (AAZ) (Ki = 12.1 nM). Compounds 6b and 6d showed moderate activity against hCA XIII (Ki= 69.8 and 65.8 nM). Hence, compound 6i could be consider as potential lead candidate for the design of potent and selective hCA II inhibitors.
Angeli, Andrea,Arifuddin, Mohammed,Biswas, Rashmita,Chinchilli, Krishna Kartheek,Korra, Laxman Naik,Supuran, Claudiu T.,Thacker, Pavitra S.
(2020/06/17)

Candida antarctica lipase-B-catalyzed kinetic resolution of 1,3-dialkyl-3-hydroxymethyl oxindoles
Candida antarctica (CAL-B) lipase-catalyzed resolution of 1,3-dialkyl-3-hydroxymethyl oxindoles has been performed to obtain (R)-1,3-dialkyl-3-acetoxymethyl oxindoles with up to 99% ee and (S)-1,3-dialkyl-3-hydroxymethyl oxindoles with up to 78% ee using vinyl acetate as acylating agent and acetonitrile as solvent transforming (S)-3-allyl-3-hydroxymethyl oxindole to (3S)-1′-benzyl-5-(iodomethyl)-4,5-dihydro-2H-spiro[furan-3,3′-indolin]-2′-one. The optically active 3-substituted-3-hydroxymethyl oxindoles and spiro-oxindoles are among the key synthons in the synthesis of potentially biologically active molecules.
Kumar, Naveen,Kumar, Akshay,Sahoo, Subash Chandra,Chimni, Swapandeep Singh
supporting information
p. 1377 - 1394
(2020/11/23)

Transformations of N-arylpropiolamides to indoline-2,3-diones and acids via C≡C triple bond oxidative cleavage and C(sp2)–H functionalization
A new palladium-catalyzed oxidative conversion of N-arylpropiolamides and H2O to various indoline-2,3-diones and acids through the C≡C triple bond cleavage and C(sp2)–H functionalization is described, which is promoted by a cooperative action of catalytic CuBr2, 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) and O2. The method provides a practical tool for transformations of alkynes by means of a C–H functionalization strategy, which enables the formation of one C–C bond and multiple C–O bonds in a single reaction with high substrates compatibility and excellent functional group tolerance.
Zhou, Ming-Bo,Li, Yang,Ouyang, Xuan-Hui,Li, Jin-Heng
p. 222 - 227
(2019/11/13)

Palladium-Catalyzed Allylation of Cyclopropyl Acetylenes with Oxindoles to Construct 1,3-Dienes
A novel palladium-catalyzed allylic alkylation of oxindoles with cyclopropyl acetylenes has been developed. Various 1,3-diene oxindole framework bearing a quaternary stereocenter at the C3 position were synthesized straightforwardly in good to excellent yields with high regio-, and stereoselectivities. The reaction exhibited high atom economy and good functional group tolerance.
Lu, Chuan-Jun,Yu, Xin,Chen, Yu-Ting,Song, Qing-Bao,Yang, Zhen-Ping,Wang, Hong
p. 680 - 688
(2020/02/11)

Acylation of oxindoles using methyl/phenyl estersviathe mixed Claisen condensation - an access to 3-alkylideneoxindoles
Predominantly, aggressive acid chlorides and stoichiometric coupling reagents are employed in the acylating process for synthesizing carbonyl tethered heterocycles. Herein, we report simple acyl sources,viz. methyl and phenyl esters, which acylate oxindolesviathe mixed Claisen condensation. This straightforward protocol is mediated by LiHMDS and KOtBu and successfully applied to a wide range of substrates. It is a noteworthy transformation that skips the stepwise generation of enolates and acylation, and the reaction is performed at a moderate temperature with no side reactions. This protocol produces the first examples ofortho-substituents in an aryl ring flanked with electron-donating and electron-withdrawing substrates. Interestingly, robust organometallic ferrocenyl methyl ester cleaved under these conditions with ease. Furthermore, biologically important Tenidap's analog was synthesized by this protocol.
Gandhi, Thirumanavelan,Nagaraja, C. M.,Panyam, Pradeep Kumar Reddy,Rajeshwaran, Purushothaman,Sreedharan, Ramdas,Yadav, Saurabh
supporting information
p. 3843 - 3847
(2020/06/03)

Site-Selective C–H Functionalization of (Hetero)Arenes via Transient, Non-symmetric Iodanes
Fosu, Hambira, and colleagues describe the direct C–H functionalization of medicinally relevant arenes or heteroarenes. This strategy is enabled by transient generation of reactive, non-symmetric iodanes from anions and PhI(OAc)2. The site-selective incorporation of Cl, Br, OMs, OTs, and OTf to complex molecules, including within medicines and natural products, can be conducted by the operationally simple procedure included herein. A computational model for predicting site selectivity is also included. The discovery of new medicines is a time- and labor-intensive process that frequently requires over a decade to complete. A major bottleneck is the synthesis of drug candidates, wherein each complex molecule must be prepared individually via a multi-step synthesis, frequently requiring a week of effort per molecule for thousands of candidates. As an alternate strategy, direct, post-synthetic functionalization of a lead candidate could enable this diversification in a single operation. In this article, we describe a new method for direct manipulation of drug-like molecules by incorporation of motifs with either known pharmaceutical value (halides) or that permit subsequent conversion (pseudo-halides) to medicinally relevant analogs. This user-friendly strategy is enabled by combining commercial iodine reagents with salts and acids. We expect this simple method for selective, post-synthetic incorporation of molecular diversity will streamline the discovery of new medicines. A strategy for C–H functionalization of arenes and heteroarenes has been developed to allow site-selective incorporation of various anions, including Cl, Br, OMs, OTs, and OTf. This approach is enabled by in situ generation of reactive, non-symmetric iodanes by combining anions and bench-stable PhI(OAc)2. The utility of this mechanism is demonstrated via para-selective chlorination of medicinally relevant arenes, as well as site-selective C–H chlorination of heteroarenes. Spectroscopic, computational, and competition experiments describe the unique nature, reactivity, and selectivity of these transient, unsymmetrical iodanes.
Fosu, Stacy C.,Hambira, Chido M.,Chen, Andrew D.,Fuchs, James R.,Nagib, David A.
supporting information
p. 417 - 428
(2019/02/14)

"on Water" Direct Organocatalytic Cyanoarylmethylation of Isatins for the Diastereoselective Synthesis of 3-Hydroxy-3-cyanomethyl Oxindoles
An "on water" organocatalytic cyanoarylmethylation of aryl acetonitrile to isatins is developed, giving products in high yields and up to excellent diastereoselectivities. A remarkable enhancement of reaction rates and diastereoselectivities by water was observed under mild conditions. Moreover, this approach provides a highly efficient and environmentally benign access to thermodynamic 3-hydroxy-3-cyanomethyl oxindoles.
Zhang, Yong,Luo, Liang,Ge, Jin,Yan, Su-Qiong,Peng, Yan-Xin,Liu, Ya-Ru,Liu, Jin-Xiang,Liu, Chong,Ma, Tianqiong,Luo, Hai-Qing
p. 4000 - 4008
(2019/03/29)

Enhancement of the tail hydrophobic interactions within the carbonic anhydrase IX active site via structural extension: Design and synthesis of novel N-substituted isatins-SLC-0111 hybrids as carbonic anhydrase inhibitors and antitumor agents
Herein we report the design and synthesis of novel N-substituted isatins-SLC-0111 hybrids (6a-f and 9a-l). A structural extension approach was adopted via N-alkylation and N-benzylation of isatin moiety to enhance the tail hydrophobic interactions within the carbonic anhydrase (CA) IX active site. Thereafter, a hybrid pharmacophore approach was utilized via merging the pharmacophoric elements of isatin and SLC-0111 in a single chemical framework. As planned, a substantial improvement of inhibitory profile of the target hybrids (KIs: 4.7–86.1 nM) towards hCA IX in comparison to N-unsubstituted leads IVa-c (KIs: 192–239 nM), was achieved. Molecular docking of the designed hybrids in CA IX active site unveiled, as planned, the ability of N-alkylated and N-benzylated isatin moieties to accommodate in a wide hydrophobic pocket formed by T73, P75, P76, L91, L123 and A128, establishing strong van der Waals interactions. Hybrid 6c displayed good anti-proliferative activity under hypoxic conditions towards breast cancer MDA-MB-231 and MCF-7 cell lines (IC50 = 7.43 ± 0.28 and 12.90 ± 0.34 μM, respectively). Also, 6c disrupted the MDA-MB-231 cell cycle via alteration of the Sub-G1 phase and arrest of G2-M stage. Additionally, 6c displayed significant increase in the percent of annexinV-FITC positive apoptotic cells from 1.03 to 18.54%. Furthermore, 6c displayed potent VEGFR-2 inhibitory activity (IC50 = 260.64 nM). Collectively, these data suggest 6c as a promising lead molecule for the development of effective anticancer agents.
Eldehna, Wagdy M.,Abo-Ashour, Mahmoud F.,Nocentini, Alessio,El-Haggar, Radwan S.,Bua, Silvia,Bonardi, Alessandro,Al-Rashood, Sara T.,Hassan, Ghada S.,Gratteri, Paola,Abdel-Aziz, Hatem A.,Supuran, Claudiu T.
p. 147 - 160
(2018/11/23)

Click-chemistry approach to synthesis of functionalized isatin-ferrocenes and their biological evaluation against the human pathogen Trichomonas vaginalis
Copper-promoted azide-alkyne cycloadditions were attempted to synthesize a series of variedly functionalized 1H-1,2,3-triazole-linked isatin-ferrocene, ferrocenylmethoxy-isatin and isatin-ferrocenyl-chalcone conjugates. The synthesized scaffolds were assayed for their inhibitory activity against T. vaginalis as well as several common normal human flora bacteria. The observed inhibitory activities against T. vaginalis and undetectable inhibition of microflora bacteria suggest that these compounds may be specific against trichomonad protozoa and could serve as a new scaffold for synthesis of novel compounds against this important human pathogen.
Singh, Amandeep,Zhang, David,Tam, Christina C.,Cheng, Luisa W.,Land, Kirkwood M.,Kumar, Vipan
p. 1 - 4
(2019/06/11)

Efficient Synthesis of Spirooxindole Pyrrolones by a Rhodium(III)-Catalyzed C?H Activation/Carbene Insertion/Lossen Rearrangement Sequence
A rhodium(III)-catalyzed domino annulation of simple olefins with diazo oxindoles to give spirooxindole pyrrolone products is described. This reaction can be formally viewed as the result of an anomalous tandem C?H activation, carbene insertion, Lossen rearrangement, and a nucleophilic addition process. The potential utility of this reaction was further demonstrated by the late-stage diversification of drug molecules.
Ma, Biao,Wu, Peng,Wang, Xing,Wang, Zhengyu,Lin, Hai-Xia,Dai, Hui-Xiong
supporting information
p. 13335 - 13339
(2019/08/20)

Preparation method of isatin derivatives
The invention discloses a preparation method of isatin derivatives. N-substituted indoline is used as raw materials; tert-butyl hydroperoxide TBHP water solution is used as an oxidizing agent; Cu(OAc)2 is used as a catalyst; the raw materials, the oxidizing agent, the catalyst and the solvent are mixed; then, reaction is performed under the condition of 75 to 95 DEG C for 5 to 30min; the reactionliquid is cooled and is then subjected to washing, extraction separation, drying, solvent removal and purification to obtain the isatin derivatives. The preparation method has the advantages that themethod can further realize the process of directly oxidizing the N-substituted indoline into the isatin derivatives; the reaction operation is simple; the requirement can be met through open opening heating; the reaction time short; the high-yield isatin compounds can be obtained only through 10 minutes; secondly, the catalyst and the oxidizing agent used in the reaction are very cheap; the reaction cost is low; when the specific reaction conditions are used for combination, the yield can reach 88 percent to the highest degree.
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Paragraph 0018; 0032

(2019/06/08)

3-Hydrazinoisatin-based benzenesulfonamides as novel carbonic anhydrase inhibitors endowed with anticancer activity: Synthesis, in vitro biological evaluation and in silico insights
Herein we describe the design and synthesis of two series of sulfonamides featuring N-unsubstituted (4a-c) or N-substituted (7a-o) isatin moieties (as tails) connected to benzenesulfonamide moiety via a hydrazine linker. All the prepared sulfonamides (4a-c and 7a-o) showed potent inhibitory activities toward transmembrane tumor-associated human (h) carbonic anhydrase (hCA, EC 4.2.1.1) isoforms, IX and XII with KI range (8.3–65.4 nM) and (11.9–72.9 nM), respectively. Furthermore, six sulfonamides (7e, 7i, 7j, 7m, 7n and 7o) were assessed for their anti-proliferative activity, according to US-NCI protocol, toward a panel of sixty cancer cell lines. Compounds 7j and 7n were the most promising counterparts in this assay displaying broad spectrum anti-proliferative activity toward diverse cell lines. Also, sulfonamide 7n significantly inhibited clonogenicity of HCT-116 cells in a concentration dependent manner in the colony forming assay. Moreover, molecular modeling studies were performed to gain insights for the plausible binding interactions and affinities for the target isatin-based sulfonamides (4a-c and 7a-o) within hCA isoforms II and IX active sites.
Abo-Ashour, Mahmoud F.,Eldehna, Wagdy M.,Nocentini, Alessio,Bonardi, Alessandro,Bua, Silvia,Ibrahim, Hany S.,Elaasser, Mahmoud M.,Kry?tof, Vladimír,Jorda, Radek,Gratteri, Paola,Abou-Seri, Sahar M.,Supuran, Claudiu T.
(2019/10/19)

CF 3 COOH/O 2 -Mediated Metal-Free Domino Construction of the Isatin Skeleton
Directed by the strategy of C-H activation, an efficient construction of the isatin skeleton was developed through aerobic oxidation of glycine esters. The reactions were performed under CF 3 COOH/O 2 conditions in the absence of met
Chen, Yongjian,Li, Jianjun,Wang, Fang,Zhang, Qiwei,Zhou, Jiadi
supporting information
p. 1799 - 1804
(2019/09/09)

Synthesis method of indole-2,3-dione compound
The invention discloses a synthesis method of an indole-2,3-dione compound. The method comprises the following steps that a raw material as shown in a formula I is added into a Schlenk reactor, then acatalyst bis(acetonitrile)dichloropalladium (PdCl2(CH3CN)2), an oxidizing agent silver acetate (AgOAc) and a solvent methylbenzene are added, reaction is carried out under an oxygen atmosphere at 120-150 DEG C for 8-36 hours, a TLC board is used for monitoring the reaction, and after the reaction is carried out completely, the indole-2,3-dione compound as shown in a formula II is obtained throughpost-treatment.
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Paragraph 0030; 0034-0036

(2018/12/05)

Palladium(II)/N-Heterocyclic Carbene Catalyzed One-Pot Sequential α-Arylation/Alkylation: Access to 3,3-Disubstituted Oxindoles
Rationally designed fluorene-based mono- and bimetallic Pd-PEPPSI complexes were synthesized and demonstrated to be effective for the one-pot sequential α-arylation/alkylation of oxindoles. This streamlined approach offers efficient access to functionalized 3,3-disubstituted oxindoles in excellent yields (up to 89%) under mild reaction conditions.
Reddy Panyam, Pradeep Kumar,Ugale, Bharat,Gandhi, Thirumanavelan
p. 7622 - 7632
(2018/06/22)

Cinchona-alkaloid-catalyzed enantioselective hydroxymethylation of 3-fluorooxindoles with paraformaldehyde
Cinchona-alkaloid-catalyzed hydroxymethylation of 3-fluorooxindoles using paraformaldehyde as the C1 unit was achieved. A wide range of 3-fluorooxindoles was successfully reacted to give the corresponding 3-fluoro-3-hydroxymethyloxindoles with high efficiency and moderate to good enantioselectivity.
Zhao, Jian-bo,Ren, Xinfeng,Zheng, Bu-quan,Ji, Jian,Qiu, Zi-bin,Li, Ya
supporting information
p. 44 - 51
(2018/10/02)

Synthesis of Spiro[oxindole-3,2′-pyrrolidine] Derivatives from Benzynes and Azomethine Ylides through 1,3-Dipolar Cycloaddition Reactions
A novel synthetic strategy employing benzyne and azomethine ylides for the construction of spiro[oxindole-3,2′-pyrrolidine] derivatives has been achieved in good yields. The ketimines obtained from the condensation of isatins with CF3CH2NH2 react with benzyne in the presence of weak bases such as TBAF or TBAT. This mild practical 1,3-dipolar cycloaddition provides an efficient route to access biologically active compounds.
Ryu, Heesun,Seo, Jeongseob,Ko, Haye Min
p. 14102 - 14109
(2018/11/21)

Oxidative Radical Cyclization of N-methyl-N-arylpropiolamide to Isatins via Cleavage of the Carbon-carbon Triple Bond
A radical cyclization of N-methyl-N-arylpropiolamide to isatins via an oxidative cleavage of a carbon-carbon triple bond has been developed. In the presence of oxone and NaNO2, a variety of N-methyl-N-arylpropiolamides were smoothly transformed into isatins. A nitration reaction proceeded along with the oxidative cyclization; both nitrated and non-nitrated isatins were obtained in a one-pot reaction with moderate to good total yields. This is the first example for the synthesis of isatins via the oxidative radical cleavage of a carbon-carbon triple bond. (Figure presented.).
Liao, Yan-Yan,Gao, Yong-Chao,Zheng, Wenxu,Tang, Ri-Yuan
p. 3391 - 3400
(2018/07/31)

NaI-mediated divergent synthesis of isatins and isoindigoes: A new protocol enabled by an oxidation relay strategy
A new approach for the synthesis of isatins and isoindigoes by an inexpensive and environmentally friendly NaI-mediated transformation is disclosed. The selectivity could be switched by simply varying the solvent, and isatins (using THF) and isoindigoes (using DMSO) could be obtained in moderate to excellent yields.
Zhang, Hong-Hua,Wang, Yong-Qiang,Huang, Long-Tao,Zhu, Long-Qing,Feng, Yi-Yue,Lu, Ying-Mei,Zhao, Quan-Yi,Wang, Xue-Qiang,Wang, Zhen
supporting information
p. 8265 - 8268
(2018/07/29)

Tumor-associated carbonic anhydrase isoform IX and XII inhibitory properties of certain isatin-bearing sulfonamides endowed with in vitro antitumor activity towards colon cancer
Three series of indolinone-based sulfonamides (3a–f, 6a–f and 9a–f) were in vitro evaluated as inhibitors of the tumor-associated carbonic anhydrase (CA, EC 4.2.1.1) isoforms hCA IX and XII, using a stopped-flow CO2 hydrase assay. All the investigated sulfonamides displayed single- or double-digit nanomolar inhibitory activities towards both hCA IX (KIs: 6.2–64.8 nM) and XII (KIs: 7.1–55.6 nM) isoforms. All sulfonamides (3a–f, 6a–f and 9a–f) were in vitro examined for their potential anticancer activity against colorectal cancer HCT-116 and breast cancer MCF-7 cell lines. Sulfonamide 9e was found to be the most potent counterpart against HCT-116 (IC50 = 3.67 ± 0.33 μM). Sulfonamide 9e displayed good selectivity profile for inhibition of the tumor-associated isoforms (CAs IX & XII) over the off-target cytosolic CAs I and II. 9e was screened for cell cycle disturbance and apoptosis induction in HCT-116 cells. It was found to persuade cell cycle arrest at G2-M stage as well as alter the Sub-G1 phase. Also, 9e induced the intrinsic apoptotic mitochondrial pathway in HCT-116 cells via down-regulation of the anti-apoptotic protein Bcl-2 level with concurrent boosting the pro-apoptotic Bax, caspase-9, caspase-3, cytochrome C and p53 levels.
Eldehna, Wagdy M.,Nocentini, Alessio,Al-Rashood, Sara T.,Hassan, Ghada S.,Alkahtani, Hamad M.,Almehizia, Abdulrahman A.,Reda, Ahmed M.,Abdel-Aziz, Hatem A.,Supuran, Claudiu T.
p. 425 - 432
(2018/09/21)

Novel [(3-indolylmethylene)hydrazono]indolin-2-ones as apoptotic anti-proliferative agents: design, synthesis and in vitro biological evaluation
On account of their significance as apoptosis inducing agents, merging indole and 3-hydrazinoindolin-2-one scaffolds is a logic tactic for designing pro-apoptotic agents. Consequently, 27 hybrids (6a–r, 9a–f and 11a–c) were synthesised and evaluated for their cytotoxicity against MCF-7, HepG-2 and HCT-116 cancer cell lines. SAR studies unravelled that N-propylindole derivatives were the most active compounds such as 6n (MCF-7; IC50=1.04 μM), which displayed a significant decrease of cell population in the G2/M phase and significant increase in the early and late apoptosis by 19-folds in Annexin-V-FTIC assay. Also, 6n increased the expression of caspase-3, caspase-9, cytochrome C and Bax and decreased the expression of Bcl-2. Moreover, compounds 6i, 6j, 6n and 6q generated ROS by significant increase in the level of SOD and depletion of the levels of CAT and GSH-Px in MCF-7.
Eldehna, Wagdy M.,Abo-Ashour, Mahmoud F.,Ibrahim, Hany S.,Al-Ansary, Ghada H.,Ghabbour, Hazem A.,Elaasser, Mahmoud M.,Ahmed, Hanaa Y. A.,Safwat, Nesreen A.
p. 686 - 700
(2018/04/02)

Novel indole-thiazolidinone conjugates: Design, synthesis and whole-cell phenotypic evaluation as a novel class of antimicrobial agents
In connection with our research program on the development of novel anti-tubercular candidates, herein we report the design and synthesis of two different sets of indole-thiazolidinone conjugates (8a,b; 11a-d) and (14a-k; 15a-h). The target compounds were evaluated for their in vitro antibacterial and antifungal activities against selected human pathogens viz. Staphylococcus aureus (Gram positiveve), Pseudomonas aeruginosa, Escherichia coli (Gram negative), Mycobacterium tuberculosis (Acid-fast bacteria), Aspergillus fumigates and Candida albicans (fungi). Moreover, eukaryotic cell-toxicity was tested via an integrated ex vivo drug screening model in order to evaluate the selective therapeutic index (SI) towards antimicrobial activity when microbes are growing inside primary immune cells. Also, the cytotoxicity towards a panel of cancer cell lines and human lung fibroblast normal cell line, WI-38 cells, was explored to assure their safety. Compound 15b emerged as a hit in this study with potent broad spectrum antibacterial (MIC: 0.39–0.98 μg/mL) and antifungal (MIC: 0.49–0.98 μg/mL) activities, in addition to its ability to kill mycobacteria M. aurum inside an infected macrophage model with good therapeutic window. Moreover, compound 15b displayed promising activity towards resistant bacteria strains MRSA and VRE with MIC values equal 3.90 and 7.81 μg/mL, respectively. These results suggest compound 15b as a new therapeutic lead with good selectivity for further optimization and development.
Abo-Ashour, Mahmoud F.,Eldehna, Wagdy M.,George, Riham F.,Abdel-Aziz, Marwa M.,Elaasser, Mahmoud M.,Abdel Gawad, Nagwa M.,Gupta, Antima,Bhakta, Sanjib,Abou-Seri, Sahar M.
p. 49 - 60
(2018/10/20)

TBHP Mediated Substrate Controlled Oxidative Dearomatization of Indoles to C2/C3-Quaternary Indolinones
Oxidative dearomatization of indoles with 70 % aqueous tert-butylhydroperoxide (TBHP) in the absence of any metal salts/organic solvents gave the corresponding C2/C3-quaternary indolinones under open-air reaction conditions. The nature of substituent on the indole nitrogen dictates the type of product formed in these reactions. Free (NH)-indoles gave C2-quaternary indolinone derivatives whilst (NR)-indoles yielded C3-quaternary indolinones as the major product. Moreover, the addition of an excess amount of TBHP also facilitated the one-pot transformation of (NR)-indoles to the corresponding isatin derivatives.
Kothandapani, Jagatheeswaran,Reddy, Singarajanahalli Mundarinti Krishna,Thamotharan, Subbiah,Kumar, Shankar Madan,Byrappa, Kullaiah,Ganesan, Subramaniapillai Selva
supporting information
p. 2762 - 2767
(2018/06/21)

Palladium-Catalyzed Oxidation of Indoles to Isatins by tert -Butyl Hydroperoxide
The combination of a Pd catalyst and tert -butyl hydroeroxide (TBHP) is a powerful catalytic system for many types of oxidative transformations. Here, we report that a Pd/TBHP system facilitates the oxidation of indoles with a range of functionalities to give the corresponding isatin derivatives in good yields.
Luo, Junfei,Gao, Shanshan,Ma, Yaorui,Ge, Guoping
supporting information
p. 969 - 973
(2018/02/09)

Synthesis of Indoline-2,3-diones by Radical Coupling of Indolin-2-ones with tert-Butyl Hydroperoxide
A novel strategy has been developed for the synthesis of indoline-2,3-diones through a metal-free radical-coupling reaction. Alkyl radicals derived from indolin-2-ones through a radical-transfer reaction combine with the tert-butylhydroperoxy radical readily generated from commercially available tert-butyl hydroperoxide to afford 3-(tertbutylperoxy)indolin-2-one intermediates that can be further transformed into indoline-2,3-diones under air. This strategy provides a simple and e?cient route to the construction of a C=O bond without the use of any metal catalyst or base.
Ying, Wei-Wei,Zhu, Wen-Ming,Liang, Hongze,Wei, Wen-Ting
supporting information
p. 215 - 218
(2017/09/28)

Spiroannulation of Oxindoles via Aryne and Alkyne Incorporation: Substituent-Diverted, Transition-Metal-Free, One-Pot Access to Spirooxindoles
A "product control via substrate design" strategy has been conceptualized and implemented to harness the potential of aryne and activated alkyne insertions into oxindoles to readily and efficiently furnish pharmacophoric indano- and cyclopentannulated spirooxindole scaffolds in an operationally straightforward, one-pot, transition-metal-free protocol.
Samineni, Ramesh,Madapa, Jaipal,Srihari, Pabbaraja,Mehta, Goverdhan
supporting information
p. 3119 - 3122
(2017/06/23)

FeCl3-Catalyzed Allylation Reactions onto 3-Hydroxy-2-oxindoles: Formal Total Syntheses of Bis-cyclotryptamine Alkaloids, (±)-Chimonanthine, and (±)-Folicanthine
An FeCl3-catalyzed efficient strategy for the allylation reactions of 3-hydroxy-2-oxindoles with allyltrimethylsilane has been developed. The reaction affords a variety of 2-oxindoles having quaternary center at the pseudobenzylic position in an operationally simple and inexpensive procedure. Control experiments using enantioenriched 3-hydroxy-2-oxindole show that the reaction proceeds through in situ generated 2H-indol-2-one (8). The methodology presents an efficient and concise access to the pyrroloindoline alkaloids (±)-deoxyeseroline (1a), (±)-esermethole (1b), (±)-physostigmine (1c), (±)-phenserine (1d), and (±)-physovenine (1e). Eventually, we extrapolated the scope of this methodology to the formal total syntheses of dimeric cyclotyrptamine alkaloids (±)-chimonanthine (3a), (±)-folicanthine (3c), and (±)-calycanthine (4).
Kinthada, Lakshmana K.,Medisetty, Sai Raghavendra,Parida, Amarchand,Babu, K. Naresh,Bisai, Alakesh
p. 8548 - 8567
(2017/08/23)

Direct N-H/α,α,β,β-C(sp3)-H functionalization of piperidine via an azomethine ylide route: synthesis of spirooxindoles bearing 3-substituted oxindoles
A protocol for the direct functionalization of N-H/α,α,β,β-C(sp3)-H of piperidine without any metal or external oxidants is reported. This reaction is promoted by 4-(trifluoromethyl)benzoic acid via an azomethine ylide intermediate. This is a simple method for the synthesis of spirooxindoles bearing 3-substituted oxindole moieties.
Du, Yanlong,Yu, Aimin,Jia, Jiru,Zhang, Youquan,Meng, Xiangtai
supporting information
p. 1684 - 1687
(2017/02/10)

Tertiary Amine-Catalyzed Difluoromethylthiolation of Morita–Baylis–Hillman Carbonates of Isatins with Zard's Trifluoromethylthiolation Reagent
In this paper, we report that a novel tertiary amine-catalyzed [3+2] annulation between Morita–Baylis–Hillman (MBH) carbonates derived from isatins with thiocarbonyl fluoride (F2C=S) in situ generated from Zard's reagent proceeds smoothly under mild conditions, affording difluoromethylthiolated spirocyclic oxindoles in good to excellent yields. Moreover, the asymmetric variant could be realized with a modified Cinchona alkaloid, giving the desired cyclic adducts in good to excellent yields with good enantioselectivities. (Figure presented.).
Fan, Xing,Yang, Haibin,Shi, Min
supporting information
p. 49 - 57
(2017/01/14)

Addition of carbamoylsilane to isatins: Highly efficient synthesis of 3-hydroxy-3-aminocarbonyl-2-oxindoles derivatives
The first addition reaction between isatins and carbamoysilane has been developed which provides 3-hydroxy-3-aminocarbonyl-2-oxindoles core structures with excellent yields. Moreover, the reaction could undergo a one-pot synthesis process to furnish 3-hydroxy-3-aminocarbonyl-2-oxindole with gram-scale.
Liang, Jin-Yan,Wang, Hui,Yang, Yan-Li,Shen, Shou-Jie,Chen, Jian-Xin
supporting information
p. 2636 - 2639
(2017/06/14)

Asymmetric Intermolecular Rauhut?Currier Reaction for the Construction of 3,3-Disubstituted Oxindoles with Quaternary Stereogenic Centers
A remote cross Rauhut?Currier reaction utilizing vinyl ketones and para-quinone methides derived from isatins was realized, which was successfully catalyzed using bifunctional phosphines, furnishing chiral 3,3-disubstituted oxindoles in excellent enantioselectivities and high yields. The mechanistic studies demonstrated the key role of the alkyl hydrogen of the vinyl ketones, which conceivably interacted with the para-quinone methide carbonyl group via the hydrogen bond, offering a new insight for the design of novel asymmetric reactions. (Figure presented.).
Wang, Hongyu,Wang, Kaiye,Man, Yunquan,Gao, Xiaonan,Yang, Limin,Ren, Yanfei,Li, Na,Tang, Bo,Zhao, Gang
supporting information
p. 3934 - 3939
(2017/11/30)

Regio- and diastereoselective construction of spirocyclopenteneoxindoles through phosphine-catalyzed [3 + 2] annulation of methyleneindolinone with alkynoate derivatives
A phosphine-catalyzed [3 + 2] annulation of isatin-derived α,β-unsaturated ketones with alkynoates for the synthesis of cyclopentene spiro-oxindole skeletons has been developed. This reaction afforded the desired products in high to excellent yields (up to 99%) with high regioselectivity and moderate to high diastereoselectivities (up to 20:1). This strategy allows facile diastereoselective preparation of biologically important spiro-(cyclopentene) oxindoles containing three contiguous stereocenters, including the quaternary stereogenic center joining the two rings.
Zhang, Jiayong,Cheng, Cheng,Wang, Dian,Miao, Zhiwei
supporting information
p. 10121 - 10128
(2018/05/31)

Double Carbonylation Using Glyoxal (HCOCOH): A Practical Copper-Promoted Synthesis of Isatins from Primary and Secondary Anilines
A novel double carbonylation process has been demonstrated with easily available HCOCOH (glyoxal) as the double carbonylation reagent. Simple CuCl2?2H2O (copper(II) chloride dihydrate) was used as the oxidant for this transformation. Under optimized reaction conditions, various primary and secondary anilines were double-carbonylated to afford their corresponding isatins (26 examples, up to 80% yields). (Figure presented.).
Kuan, Suzie Hui Chin,Sun, Wei,Wang, Lu,Xia, Chungu,Tay, Meng Guan,Liu, Chao
supporting information
p. 3484 - 3489
(2017/09/06)

Novel indolin-2-one-based sulfonamides as carbonic anhydrase inhibitors: Synthesis, in?vitro biological evaluation against carbonic anhydrases isoforms I, II, IV and VII and molecular docking studies
Herein we present the design, synthesis, and biological evaluation of three different series of novel sulfonamides (3a-f, 6a-f and 9a-f) incorporating substituted indolin-2-one moieties (as tails) linked to benzenesulfonamide (as zinc anchoring moieties) through aminoethyl or (4-oxothiazolidin-2-ylidene)aminoethyl linkers. The synthesized sulfonamides were evaluated in?vitro for their inhibitory activity against the following human (h) carbonic anhydrase (hCA, EC 4.2.1.1) isoforms, hCA I, II, IV and VII. All these isoforms were inhibited by the sulfonamides reported here in variable degrees. hCA I was inhibited with KIs in the range of 42–8550.9?nM, hCA II in the range of 5.9–761?nM; hCA IV in the range of 4.0–2069.5?nM, whereas hCA VII in the range of 13.2–694?nM. Molecular docking studies were carried out for some of the tested compounds within the hCA II active site, allowed us to rationalize the obtained inhibition results.
Eldehna, Wagdy M.,Al-Ansary, Ghada H.,Bua, Silvia,Nocentini, Alessio,Gratteri, Paola,Altoukhy, Ayman,Ghabbour, Hazem,Ahmed, Hanaa Y.,Supuran, Claudiu T.
p. 521 - 530
(2017/01/24)

Novel 4/3-((4-oxo-5-(2-oxoindolin-3-ylidene)thiazolidin-2-ylidene)amino) benzenesulfonamides: Synthesis, carbonic anhydrase inhibitory activity, anticancer activity and molecular modelling studies
Herein we report the synthesis of two series of novel 4/3-((4-oxo-5-(2-oxoindolin-3-ylidene)thiazolidin-2-ylidene)amino)benzenesulfonamides (4a-m and 7a-g). All the newly prepared sulfonamides were in vitro investigated as inhibitors of the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1) isoforms hCA I, II, IV and IX, using a stopped-flow CO2 hydrase assay. In particular, hCA isoforms II and IX (tumor-associated) were more susceptible to inhibition by the synthesized derivatives, with KIs in the range of 2.6–598.2 nM for hCA II, and of 16.1–321 nM for hCA IX. All compounds (4a-m and 7a-g) were evaluated for their anti-proliferative activity against breast cancer MCF-7 and colorectal cancer Caco-2 cell lines. Compound 4c was found to be the most potent derivative against MCF-7 (IC50 = 3.96 ± 0.21 μM), while 4j was the most active member against Caco-2 cells (IC50 = 5.87 ± 0.37 μM). Compound 4c induced the intrinsic apoptotic mitochondrial pathway in MCF-7 cells; evidenced by the enhanced expression of the pro-apoptotic protein Bax and the reduced expression of the anti-apoptotic protein Bcl-2, and the up-regulated active caspase-9 and caspase-3 levels.
Eldehna, Wagdy M.,Abo-Ashour, Mahmoud F.,Nocentini, Alessio,Gratteri, Paola,Eissa, Ibrahim H.,Fares, Mohamed,Ismael, Omnia E.,Ghabbour, Hazem A.,Elaasser, Mahmoud M.,Abdel-Aziz, Hatem A.,Supuran, Claudiu T.
p. 250 - 262
(2017/08/14)

Synthesis and bio-evaluation of quaternary centered 3-hydroxy-3-(trifluoromethyl)indolin-2-one derivatives for anticancer and antimicrobial activities
Abstract: A series of C(3)-trifluoromethylated compounds derived from N-substituted isatins were synthesized. The biological activity of all 3-hydroxy-3-(trifluoromethyl)indolin-2-one derivatives have been evaluated for in vitro cytotoxic activity and antibacterial activity. The active compounds were screened against nuclear xenobiotic receptor CAR (PDB ID: 1XLS), PIM1 kinase (PDB ID: 2O65), and CDK2 kinase (PDB ID: 3QHR) by using in silico molecular docking studies to obtain lead molecules. In addition to its potential anticancer activity, 5-bromo-3-ethynyl-3-hydroxy-1-(prop-2-yn-1-yl)indolin-2-one also showed specific antibacterial activity against S. aureus. Graphical abstract: [Figure not available: see fulltext.]
Bikshapathi, Raktani,Prathima, Parvathaneni Sai,Yashwanth,Pamanji,Jagadeeshkumar,Maheshwari,Rao, J. Venkateswara,Murty,Rao, V. Jayathirtha
p. 757 - 764
(2017/03/17)

Cu-catalyzed oxidation of indoles to isatins
The first example of Cu-catalyzed oxidation of indoles to isatin derivatives by the use of cheap aqueous tert-butyl peroxide as an oxidant was developed. This methodology is practically convenient and highly functional group tolerant, allowing a variety of indole derivatives to transform into the corresponding isatin derivatives in good yields.
Luo, Junfei,Zhao, Yanchao,Xu, Xing,Zheng, Junliang,Liang, Hongze
supporting information
p. 4591 - 4594
(2017/11/15)

Diversity-Oriented Synthesis of Oxacyclic Spirooxindole Derivatives through Ring-Closing Enyne Metathesis and Intramolecular Pauson–Khand (2+2+1) Cyclization of Oxindole Enynes
An efficient approach for a reagent-based diversity-oriented synthesis (DOS) of novel fused spirooxindole scaffolds from oxindole enynes has been developed. The reaction involves a metal-catalyzed C-3 allylation/vinylation/homoallylation of N-substituted isatins which gives rise to the corresponding alcohols that can be converted into the required enynes. Further transformation to diverse complex molecular scaffolds proceeds via a subsequent ruthenium-catalyzed ring-closing enyne metathesis (RCEYM), or cobalt-catalyzed intramolecular Pauson–Khand (2+2+1) cyclization reaction (IPKR). This strategy provides a facile approach to various spirooxindole-vinyldihydropyrans/tetrahydrooxepines and spirocyclic fused cyclopentenones in good to excellent yields. (Figure presented.).
Kandimalla, Satheeshkumar Reddy,Sabitha, Gowravaram
supporting information
p. 3444 - 3453
(2017/09/25)

Copper-catalyzed aerobic oxidative intramolecular amidation of 2-aminophenylacetylenes: A domino process for the synthesis of isatin
A novel CuI-catalyzed oxidative amidation of 2-aminophenylacetylenes leading to the formation of isatins by using open air as an oxygen source has been developed. The reaction proceeded smoothly and provided a variety of isatin derivatives in good yields. The advantages of this one-pot reaction protocol include the use of a green oxidant, low-price catalyst and facile conditions, and easy handling.
Salvanna,Ramesh, Perla,Santosh Kumar,Das, Biswanath
p. 13754 - 13759
(2017/11/27)

Convenient and Clean Synthesis of Isatins by Metal-Free Oxidation of Oxindoles
A metal-free synthesis of isatins was achieved through the oxidative reactions of oxindoles with molecular oxygen in the presence of tert -butyl nitrite as an additive. This strategy provides a convenient and simple synthetic route to the construction of C=O bonds without the need for any catalyst or base. The attractive features of this reaction include its convenient procedure and mild reaction conditions.
Wei, Wen-Ting,Ying, Wei-Wei,Zhu, Wen-Ming,Wu, Yi,Huang, Yi-Ling,Cao, Yi-Qi,Wang, Yi-Ning,Liang, Hongze
supporting information
p. 2307 - 2310
(2017/10/06)

Active sp3 C-H Bond Oxidation Initiated sp3-sp2 Consecutive C-H Functionalization of N-Arylglycine Amides: Construction of Isatins
In the presence of catalytic triarylamine radical cation, an sp3-sp2 consecutive C-H functionalization of N-arylglycine amides was achieved, providing a series of isatin derivatives in high yields. In this transformation, the initial aerobic oxidation of the relatively active sp3 C-H bonds triggered the following intramolecular cyclization, in which the aniline group was employed as a removable auxiliary group to enable the consecutive process.
Ji, Honghe,Zhu, Yingzu,Shao, Yu,Liu, Jing,Yuan, Yu,Jia, Xiaodong
p. 9859 - 9865
(2017/09/23)

Ferric(III) chloride catalyzed intramolecular cyclization of N-alkyl-2-oxo-acetanilides: A facile access to isatins
A facile strategy for the synthesis of isatins in high yield from N-alkyl-2-oxo-acetanilides has been developed via Friedel-Crafts alkylation using FeCl3 as catalyst under air. This reaction proceeds through direct intramolecular addition and oxidation in one pot. Also this methodology is operationally simple, atom economical, and environment friendly.
Zheng, Yang,Li, Jue,Yu, Xinling,Lv, Songyang,Hai, Li,Wu, Yong
supporting information
p. 39 - 42
(2015/12/24)

First Report on the Synthesis of Isatins via Pyridinium Chlorochromate Catalyzed Intramolecular Cyclization Reactions
A new and useful strategy to synthesize isatins from α-formyl amides has been developed via one-pot intramolecular cyclization-oxidation reaction with the present of pyridinium chlorochromate (PCC). The reaction proceeded smoothly under air and has good yields of the corresponding products. Also, this methodology has a broad substrate scope, and is operationally simple and atom economic.
Yue, Qiming,Wang, Yaoling,Hai, Li,Guo, Li,Yin, Hongmei,Wu, Yong
supporting information
p. 1292 - 1296
(2016/05/10)