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Copolymerization of an indazole ligand into the self-polymerization of dopamine for enhanced binding with metal ions
5,6-Dihydroxy-1H-indazole (DHI) is able to self-polymerize through the same mussel-inspired chemistry responsible for generating poly(dopamine) (PDA), demonstrating the potential to expand this class of catecholamine-exclusive chemistry onto heterocyclic catechol derivatives for the preparation of functional materials. Although DHI exhibits slower polymerization kinetics compared to dopamine, the two chemical species are compatibly polymerizable under the same reaction conditions and allow the preparation of copolymer coatings in different molar ratios. Of these copolymers, the 1:3-copolymer (DHI-to-dopamine ratio) has demonstrated adequate structural stability as a polymer coating. While PDA performs as an intact framework, the incorporated DHI enhances the colloidal stability and provides additional coordinating functionality through the pyrazole moieties. The 1:3-copolymer was fabricated into polymer capsules which exhibit negligible cytotoxicity towards murine dermal fibroblasts (L929) and enhanced binding behaviour towards copper(ii). This represents a new channel for fabricating cargo carriers for biomedical applications that involve the use of transition metal-based species.
Fan, Ka Wai,Roberts, Justine J.,Martens, Penny J.,Stenzel, Martina H.,Granville, Anthony M.
p. 7457 - 7465
(2015)
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Diphyllin and application thereof in preparation of medicine for preventing or treating diabetes mellitus
The invention belongs to the technical field of medicine, and particularly relates to diphyllin represented by a formula I and an application of the diphyllin in preparation of medicine for preventingor treating diabetes mellitus, and experiments prove that the compound can improve insulin sensitivity of mice and reduce blood sugar. The compound is expected to be developed into a medicine for preventing or treating diabetes.
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Paragraph 0029-0031

(2020/06/05)

Diphyllin Improves High-Fat Diet-Induced Obesity in Mice Through Brown and Beige Adipocytes
Brown adipose tissue (BAT) and beige adipose tissue dissipate metabolic energy and mediate nonshivering thermogenesis, thereby boosting energy expenditure. Increasing the browning of BAT and beige adipose tissue is expected to be a promising strategy for combatting obesity. Through phenotype screening of C3H10-T1/2 mesenchymal stem cells, diphyllin was identified as a promising molecule in promoting brown adipocyte differentiation. In vitro studies revealed that diphyllin promoted C3H10-T1/2 cell and primary brown/beige preadipocyte differentiation and thermogenesis, which resulted increased energy consumption. We synthesized the compound and evaluated its effect on metabolism in vivo. Chronic experiments revealed that mice fed a high-fat diet (HFD) with 100 mg/kg diphyllin had ameliorated oral glucose tolerance and insulin sensitivity and decreased body weight and fat content ratio. Adaptive thermogenesis in HFD-fed mice under cold stimulation and whole-body energy expenditure were augmented after chronic diphyllin treatment. Diphyllin may be involved in regulating the development of brown and beige adipocytes by inhibiting V-ATPase and reducing intracellular autophagy. This study provides new clues for the discovery of anti-obesity molecules from natural products.
Duan, Ya-Nan,Ge, Xiang,Jiang, Hao-Wen,Zhang, Hong-Jie,Zhao, Yu,Li, Jin-Long,Zhang, Wei,Li, Jing-Ya
(2020/12/28)

COMPOUNDS FOR THE INHIBITION OF UNREGULATED CELL GROWTH
The present invention discloses compounds for inhibition of uncontrolled cell proliferation particularly cancer stem cells. Particularly, the invention relates to compounds of Formula I to XXII for the treatment of cancer.
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Page/Page column 34

(2020/07/14)

Solvent-free oxidation of benzyl alcohols catalysed by a tetrazole-saccharinate Zn(II) complex under microwave radiation: The role of the ligand and the reaction mechanism
Herein we present an efficient methodology for the microwave-assisted peroxidative oxidation of benzyl alcohols to the corresponding aldehydes by using a novel and stable tetrazole-saccharinate zinc(II) catalyst, along with some insights into the reaction mechanism. This methodology is distinguished by the use of easily available and cheap reagents on the genesis of the zinc catalyst, mild reaction conditions, very short reaction periods (5–20 min) and no need to add an organic solvent. Furthermore, the use of TBHP (70percent. aq.) as oxidizing agent turn this protocol a convenient one for benzyl alcohol oxidation in yields up to 98percent.
Cristiano, M. Lurdes S.,Fernandes, André L.,Frija, Luís M. T.,Pombeiro, Armando J. L.
(2020/07/27)

Palladium-catalyzed ortho-C(sp2)[sbnd]H bromination of benzaldehydes via a monodentate transient directing group strategy
A facile and efficient monodentate transient directing group strategy was developed to enable the palladium-catalyzed ortho-C(sp2)[sbnd]H bromination of benzaldehydes. A broad scope of benzaldehydes were transformed into the desired products by employing 2-amino-5-chlorobenzotrifluoride as a monodentate transient directing group, demonstrating good functional group tolerance. Mild reaction conditions and no requirement for a silver salt are also features of this strategy.
Yong, Qiyun,Sun, Bing,Zhang, Fang-Lin
supporting information

(2019/11/03)

Convergent First Total Synthesis of Melovinone: A Densely Substituted 3-Methoxy-4-quinolone Isolated from Melochia tomentosa L
The first total synthesis of melovinone, a nonrutaceous 3-methoxy-4-quinolone alkaloid isolated from Melochia tomentosa L., is reported. The target was acquired in a convergent fashion through the Suzuki-Miyaura cross-coupling reaction between an ortho-nitrobenzoic acid acetonyl ester derivative prepared from vanillin and potassium 5-phenyl-1-pentyltrifluoroborate, obtained from β-phenethyl bromide. The coupling was followed by a chemoselective reduction of the nitro group and a microwave-Assisted and AcOH-promoted cyclization with rearrangement of the resulting acetonyl anthranilate. This afforded a pseudane intermediate, which was selectively methylated on the 3-OH. The synthetic pathway enabled to reach the objective in 11 steps and 18% overall yield. The 1 H NMR spectra of the synthetic and natural product were in full agreement.
Aguilar, Abel A. Arroyo,Kaufman, Teodoro S.,Larghi, Enrique L.,Ledesma, Gabriela N.,Tirloni, Bárbara
p. 4253 - 4262
(2019/11/14)

Biomimetic Organocatalytic Approach to 4-Arylquinolizidine Alkaloids and Application in the Synthesis of (-)-Lasubine II and (+)-Subcosine II
An enantioselective, biomimetic organocatalytic synthesis of 4-arylquinolizidin-2-ones, key intermediates in the synthesis of several Lythraceae alkaloids, was developed. The methodology features S-proline-mediated Mannich/aza-Michael reactions of readily available arylideneacetones and Δ1-piperideine. The total syntheses of (-)-lasubine II and (+)-subcosine II as well as the formal syntheses of structurally related Lythraceae alkaloids were achieved. The use of Δ1-pyrroline in the Mannich/aza-Michael reaction provides enantiomerically enriched 5-arylindolizidin-7-ones, which are precursors to nonopiate antinociceptive agents.
Virk, Seerat,Pansare, Sunil V.
supporting information
p. 5524 - 5528
(2019/07/08)

Synthesis of substituted biphenyl methylene indolinones as apoptosis inducers and tubulin polymerization inhibitors
A new series of biphenyl methylene indolinones has been designed, synthesized and evaluated for their in vitro antiproliferative activity against various cancer cell lines like DU-145 (prostate cancer cell line), 4T1 (mouse breast cancer cell line), MDA-MB-231 (human breast cancer cell line), BT-549 (human breast cancer cell line), T24 (human urinary bladder carcinoma cell line), and HeLa (cervical cancer cell line). Among the series, compound 10e showed potent in vitro cytotoxic activity against HeLa and DU-145 cancer cell lines with IC50 value of 1.74 ± 0.69 μM and 1.68 ± 1.06 μM respectively. To understand the underlying mechanism of most potent cytotoxic compound 10e, various mechanistic studies were carried out on DU-145 cell lines. Cell cycle analysis results revealed that these conjugates affect both G0/G1 and G2/M phase of the cycle, tubulin binding assay resulted that compound 10e interrupting microtubule network formation by inhibiting tubulin polymerization with IC50 value of 4.96 ± 0.05 μM. Moreover, molecular docking of 10e on colchicine binding site of the tubulin explains the interaction of 10e with tubulin. Clonogenic assay indicated inhibition of colony formation by compound 10e in a dose dependent manner. In addition, morphological changes were clearly observed by AO/EB and DAPI staining studies. Moreover, ROS detection using DCFDA, JC-1, and annexin V-FITC assays demonstrated the significant apoptosis induction by 10e.
Donthiboina, Kavitha,Anchi, Pratibha,Sri Ramya,Karri, Shailaja,Srinivasulu, Gannoju,Godugu, Chandraiah,Shankaraiah, Nagula,Kamal, Ahmed
p. 210 - 223
(2019/02/06)

Discovery of Novel Bromophenol-Thiosemicarbazone Hybrids as Potent Selective Inhibitors of Poly(ADP-ribose) Polymerase-1 (PARP-1) for Use in Cancer
Poly(ADP-ribose) polymerase-1 (PARP-1) is a new potential target for anticancer drug discovery. A series of bromophenol-thiosemicarbazone hybrids as PARP-1 inhibitors were designed, synthesized, and evaluated for their antitumor activities. Among them, the most promising compound, 11, showed excellent selective PARP-1 inhibitory activity (IC50 = 29.5 nM) over PARP-2 (IC50 > 1000 nM) and potent anticancer activities toward the SK-OV-3, Bel-7402 and HepG2 cancer cell lines (IC50 = 2.39, 5.45, and 4.60 μM), along with inhibition of tumor growth in an in vivo SK-OV-3 cell xenograft model. Further study demonstrated that compound 11 played an antitumor role through multiple anticancer mechanisms, including the induction of apoptosis and cell cycle arrest, cellular accumulation of DNA double-strand breaks, DNA repair alterations, inhibition of H2O2-triggered PARylation, antiproliferative effects via the production of cytotoxic reactive oxygen species, and autophagy. In addition, compound 11 displayed good pharmacokinetic characteristics and favorable safety. These observations demonstrate that compound 11 may serve as a lead compound for the discovery of new anticancer drugs.
Guo, Chuanlong,Wang, Lijun,Li, Xiuxue,Wang, Shuaiyu,Yu, Xuemin,Xu, Kuo,Zhao, Yue,Luo, Jiao,Li, Xiangqian,Jiang, Bo,Shi, Dayong
p. 3051 - 3067
(2019/03/29)

A novel selenoflavone compound as anti-obesity agent
The present invention relates to a process for producing a novel selenoflavone compound and a pharmaceutical composition for preventing or treating obesity comprising the selenoflavone compound. In the present invention, selenoflavone, especially PMSF, which has never been synthesized due to synthetic difficulties can be synthesized through palladium-catalyzed direct C-H arylation. Since the synthesized selenoflavone has an improving effect related to activation of brown adipose tissue (BAT), the selenoflavone can be used in the composition for prevention and treatment of obesity.COPYRIGHT KIPO 2018
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Paragraph 0177; 0181; 0207-0210; 0212

(2018/12/01)

Regioselective Halogenation of Arenes and Heterocycles in Hexafluoroisopropanol
Regioselective halogenation of arenes and heterocycles with N-halosuccinimides in fluorinated alcohols is disclosed. Under mild condition reactions, a wide diversity of halogenated arenes are obtained in good yields with high regioselectivity. Additionally, the versatility of the method is demonstrated by the development of one-pot sequential halogenation and halogenation-Suzuki cross-coupling reactions.
Tang, Ren-Jin,Milcent, Thierry,Crousse, Benoit
p. 930 - 938
(2018/01/28)

Practical, mild and efficient electrophilic bromination of phenols by a new I(iii)-based reagent: The PIDA-AlBr3 system
A practical electrophilic bromination procedure for phenols and phenol-ethers was developed under efficient and very mild reaction conditions. A broad scope of arenes was investigated, including the benzimidazole and carbazole core as well as analgesics such as naproxen and paracetamol. The new I(iii)-based brominating reagent PhIOAcBr is operationally easy to prepare by mixing PIDA and AlBr3. Our DFT calculations suggest that this is likely the brominating active species, which is prepared in situ or isolated after centrifugation. Its stability at 4 °C after preparation was confirmed over a period of one month and no significant loss of its reactivity was observed. Additionally, the gram-scale bromination of 2-naphthol proceeds with excellent yields. Even for sterically hindered substrates, a moderately good reactivity is observed.
Satkar, Yuvraj,Ramadoss, Velayudham,Nahide, Pradip D.,García-Medina, Ernesto,Juárez-Ornelas, Kevin A.,Alonso-Castro, Angel J.,Chávez-Rivera, Ruben,Jiménez-Halla, J. Oscar C.,Solorio-Alvarado, César R.
p. 17806 - 17812
(2018/05/28)

ANTICANCER COMPOUNDS
The present invention discloses compounds for inhibition of uncontrolled cell proliferation particularly in cancer stem cells. Particularly, the invention relates to compounds of Formula III to XIV for the treatment of cancer, such as breast and prostate cancer.
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(2018/11/22)

Thermolytic Synthesis of Naphthalenes via Intramolecular Cyclocondensation of o -Phenylallylbenzaldehydes
The development of intramolecular carbonyl-ene type cyclocondensation of oxygenated o -phenylallylbenzaldehydes in refluxing decalin is reported. The facile and easy-to-operate thermolytic rearrangement procedure generates substituted naphthalenes in good to excellent yields.Georg Thieme Verlag Stuttgart - New York.
Chang, Meng-Yang,Hsueh, Nai-Chen
p. 3408 - 3419
(2018/06/20)

Efficient synthesis of polymethoxyselenoflavones via regioselective direct C-H arylation of selenochromones
Substantial research has suggested that the configuration and the total number of functional groups on flavones influence their bioactivity. To investigate the changes in the biological activities of selenoflavones in relationship to structural changes, the development of a generally applicable synthetic method was a key. Until now, an efficient pathway for palladium-catalyzed direct arylation with the selenocyclic enone systems is not known in the literature. We herein introduce a simple direct C-H arylation of two difficult coupling partners, selenochromones and electron-rich aryl bromide, affording diverse polymethoxyselenoflavones with great efficiency and high selectivity.
Yang, Woo-Ram,Choi, Yong-Sung,Jeong, Jin-Hyun
supporting information
p. 3074 - 3083
(2017/04/10)

Synthesis of 5 - methoxy - 4 - hydroxy - 2 - boric acid aldehyde group benzenefrequency alcohol ester (by machine translation)
The invention provides a method for synthesizing 5 - methoxy - 4 - hydroxy - 2 - boric acid aldehyde group benzenefrequency alcohol ester. In particular, the invention relates to 3, 4 - dimethoxy formaldehyde as raw materials through the bromo to obtain 3, 4 - dimethoxy - 2 - bromophenylacetic formaldehyde, then by removing methyl 5 - hydroxy - 4 - methoxy - 2 - bromophenylacetic formaldehyde, then tert-butyl diphenyl silicon to protect hydroxyl to obtain 5 - tert-butyl diphenyl siloxy - 4 - methoxy - 2 - bromophenylacetic formaldehyde, then in order to glycerol acetal protected aldehyde group, then in BuLi under the action of triisopropyl borate reaction to obtain 5 - methoxy - 4 - tert-butyl diphenyl siloxy - 2 - aldehyde group benzene boric acid, then silicon protecting group to obtain 5 - methoxy - 4 - hydroxy - 2 - boric acid aldehyde group benzene, finally with the pinacone reaction ester to obtain the target product 5 - methoxy - 4 - hydroxy - 2 - boric acid aldehyde group benzenepinacone ester. The invention raw materials are easy, low cost, high yield, easy industrialization. (by machine translation)
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Paragraph 0048; 0049; 0050; 0051

(2017/08/29)

Potent Inhibitor of Drug-Resistant HIV-1 Strains Identified from the Medicinal Plant Justicia gendarussa
Justicia gendarussa, a medicinal plant collected in Vietnam, was identified as a potent anti-HIV-1 active lead from the evaluation of over 4500 plant extracts. Bioassay-guided separation of the extracts of the stems and roots of this plant led to the isolation of an anti-HIV arylnaphthalene lignan (ANL) glycoside, patentiflorin A (1). Evaluation of the compound against both the M-and T-Tropic HIV-1 isolates showed it to possess a significantly higher inhibition effect than the clinically used anti-HIV drug AZT. Patentiflorin A and two congeners were synthesized, de novo, as an efficient strategy for resupply as well as for further structural modification of the anti-HIV ANL glycosides in the search for drug leads. Subsequently, it was determined that the presence of a quinovopyranosyloxy group in the structure is likely essential to retain the high degree of anti-HIV activity of this type of compounds. Patentiflorin A was further investigated against the HIV-1 gene expression of the R/U5 and U5/gag transcripts, and the data showed that the compound acts as a potential inhibitor of HIV-1 reverse transcription. Importantly, the compound displayed potent inhibitory activity against drug-resistant HIV-1 isolates of both the nucleotide analogue (AZT) and non-nucleotide analogue (nevaripine). Thus, the ANL glycosides have the potential to be developed as novel anti-HIV drugs.
Zhang, Hong-Jie,Rumschlag-Booms, Emily,Guan, Yi-Fu,Wang, Dong-Ying,Liu, Kang-Lun,Li, Wan-Fei,Nguyen, Van H.,Cuong, Nguyen M.,Soejarto, Djaja D.,Fong, Harry H. S.,Rong, Lijun
p. 1798 - 1807
(2017/06/28)

PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE 4-HYDROXY-1,2,3,4 -TETRAHYDROQUINOLINES
The present invention relates to a method for preparing an optically active 4-hydroxy-1,2,3,4-tetrahydroquinoline compound [I], which comprises the steps of: treating a racemic 4-hydroxy-1,2,3,4-tetrahydroquinoline compound represented by general formula [I]: [wherein R 1 represents a hydrogen atom or a protecting group for amino group.] with an enzyme having an ability of selectively or preferentially acylating one enantiomer of the racemic compound [I] in the presence of an acyl donor; and if necessary, subjecting the reaction product to solvolysis.
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Paragraph 0068

(2016/07/27)

Tandem Pd-catalyzed C-C coupling/recyclization of 2-(2-bromoaryl)cyclopropane-1,1-dicarboxylates with primary nitro alkanes
The first successful synthesis of 1H-2,3-benzoxazine 3-oxides has been described. The efficiency of the approach is provided by the C-C-coupling of 2-(2-bromoaryl)cyclopropane-1,1-dicarboxylates with primary nitroalkanes catalyzed by Pd(dba)2/JohnPhos system followed by in situ recyclization of the intermediates. Several representative transformations allowing selective modification of the nitronate as well as malonate functionalities in the resulting compounds are demonstrated.
Mikhaylov, Andrey A.,Dilman, Alexander D.,Novikov, Roman A.,Khoroshutina, Yulia A.,Struchkova, Marina I.,Arkhipov, Dmitry E.,Nelyubina, Yulia V.,Tabolin, Andrey A.,Ioffe, Sema L.
supporting information
p. 11 - 14
(2015/12/23)

Synthesis of analogues of natural antimitotic glaziovianin A based on dill and parsley seed essential oils
Glaziovianin A and its analogues were synthesized in six steps starting from allylpolyalkoxybenzenes separated from essential oils of dill (Anetum graviolens) and parsley (Petro-selinum sativum) seeds.
Tsyganov, Dmitry V.,Konyushkin, Leonid D.,Semenova, Marina N.,Semenov, Victor V.
p. 285 - 287
(2016/08/09)

Synthesis and crystal structure of (4s)-4-benzyl-3-(4,5-dimethoxy-2-methylbenzoyl)- 2,2-dimethyl-1,3-oxazolidine
The synthesis of (4S)-4-benzyl-3-(4,5-dimethoxy-2-methylbenzoyl)- 2,2-dimethyl-1,3-oxazolidine 6 was performed in 7 steps starting from veratraldehyde 7. A new oxidizing system TBHP-ebselen 12 was used for oxidation of 4,5-dimethoxy-2-methylbenzaldehyde 11 into carboxylic acid 13, being the crucial step of the synthesis. The latter was transformed first to chiral amide 14 using (S)-phenylalaninol and then cyclised to oxazolidine 6. The spatial structure and the absolute configuration of the latter one was confirmed by X-ray study.
Chrzanowskak, Maria,Meissner, Zofia,Chrzanowska, Joanna M.,Gzella, Andrzej K.
p. 730 - 739
(2015/03/04)

Expedient Iodocyclization Approach Toward Polysubstituted 3H-Benzo[e]indoles
A facile and expedient iodocyclization of 4-(2-prop-1-ynylphenyl)-1H-pyrroles towards the synthesis of polysubstituted 3H-benzo[e]indoles is reported. The transformation was optimized and the best results were obtained by using iodine (1.2 equiv,) in dichloromethane, and potassium carbonate as base. The starting 1,2,3,4-tetrasubstituted pyrroles were efficiently obtained by means of a nickel(II) chloride-promoted four-component (nitromethane, amine, 2-alkynylbenzaldehyde and ethyl acetoacetate) reaction. Further functionalization of the resulting 5-iodoheterocycles was also explored.
Martins, Guilherme M.,Zeni, Gilson,Back, Davi F.,Kaufman, Teodoro S.,Silveira, Claudio C.
supporting information
p. 3255 - 3261
(2015/11/03)

Synthesis of Lamellarin D Trimethyl Ether and Lamellarin H via 6π-Electrocyclization
An electrocyclic ring closure of a 2-azapentadienyl anion generated in situ from a chalcone and glycine ester is the key step of an efficient synthesis of the pyrrole core of the lamellarin alkaloids. A recently developed scalable one-pot procedure provides multigram quantities of a 3,5-diaryl-4-iodopyrrole-2-carboxylate intermediate which is transformed in four further high-yielding operations including a one-pot Pomeranz-Fritsch alkylation/cyclization and an Ullmann-type lactone ring closure into the pentacyclic lamellarin skeleton.
Dialer, Clemes,Imbri, Dennis,Hansen, Steven Peter,Opatz, Till
p. 11605 - 11610
(2015/12/01)

THE 5,6-DIMETHOXY-1, 1-DIOXOBENZO(B)THIOPHENE-2-METHYLOXYCARBONYL (DM-BSMOC) AND RELATED AMINO-PROTECTING GROUPS
Amino acid protecting groups are provided for use in peptide synthesis. Particular compounds disclosed include 5,6-dimethoxy-l,l-dioxobenzo[b]thiophi methyloxycarbonyl (DM-Bsmoc) and related amino-protecting groups.
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Page/Page column 12; 20

(2015/02/02)

Water-soluble isoindolo[2,1-a]quinoxalin-6-imines: In vitro antiproliferative activity and molecular mechanism(s) of action
Water-soluble isoindoloquinoxalin (IIQ) imines and the corresponding acetates were conveniently prepared from the key intermediates 2-(2′-aminophenyl)-2H-isoindole-1-carbonitriles obtained by a Strecker reaction between substituted 1,2-dicarbaldehydes and 1,2-phenylenediamines. Both series were screened by the National Cancer Institute (Bethesda, MD) and showed potent antiproliferative activity against a panel of 60 human tumor cell lines. Several of the novel compounds showed GI50 values at a nanomolar level on the majority of the tested cell lines. Among IIQ derivatives, methoxy substituents at positions 3 and 8 or/and 9 were especially effective in impairing cell cycle progression and inducing apoptosis in cancer cells. These effects were associated to IIQ-mediated impairment of tubulin polymerization at pharmacologically significant concentrations of tested compounds. In addition, impaired DNA topoisomerase I functions and perturbation in telomere architecture were observed in cells exposed to micromolar concentrations of IIQ derivatives. The above results suggest that IIQ derivatives exhibit multi-target cytotoxic activities.
Parrino, Barbara,Carbone, Anna,Ciancimino, Cristina,Spanò, Virginia,Montalbano, Alessandra,Barraja, Paola,Cirrincione, Girolamo,Diana, Patrizia,Sissi, Claudia,Palumbo, Manlio,Pinato, Odra,Pennati, Marzia,Beretta, Giovanni,Folini, Marco,Matyus, Peter,Balogh, Balázs,Zaffaroni, Nadia
p. 149 - 162
(2015/03/18)

Fe(III)-catalyzed trityl benzyl ether formation and disproportionation cascade reactions to yield benzaldehydes
During investigating water-compatible Lewis acids catalyzed etherifications using alcohols as alkylating reagents directly, we developed Fe(III)-catalyzed trityl benzyl ether formations irradiated by microwave. Then an in situ trityl benzyl ether formation and disproportionation cascade reaction was achieved to yield the benzaldehyde products with good functional group tolerances under neat conditions at relative higher temperatures. The substituent effects of the substrates on the etherification and disproportionation were explored by changing the substitutions on benzyl alcohols and triarylmethanols using chemical kinetic plots methods and the mechanism of the transformation was studied by crossover experiments. The etherification and disproportionation cascade process could be conveniently scaled up in laboratory without losing much efficiency.
Wang, Xiaoyu,Du, Chuan,Shi, Hui,Pang, Yadong,Jin, Shengfei,Hou, Yuqian,Wang, Yanshi,Peng, Xiaoshi,Xiao, Jianyong,Liu, Yang,Liu, Yongxiang,Cheng, Maosheng
p. 6744 - 6748
(2015/08/24)

Selective Oxidation of Benzyl Alcohols to Aldehydes with a Salophen Copper(II) Complex and tert-Butyl Hydroperoxide at Room Temperature
(Figure Presented) An efficient and selective oxidation of benzyl alcohols has been developed using a salophen copper(II) complex as the catalyst and tert-butyl hydroperoxide (TBHP) as the oxidant in the presence of base. Moderate to excellent yields of the corresponding benzaldehydes were obtained at room temperature without the carboxylic acids being formed.
Chen, Tingting,Cai, Chun
supporting information
p. 1334 - 1341
(2015/05/27)

Synthesis and cytotoxicity evaluation of a novel justicidin G analogue and its phosphate ester
The novel justicidin G analogue 13 and its phosphate ester 15 were synthesized as potential anticancer agents in several steps starting from commercially available methyl gallate and veratraldehyde. The cytotoxicity of the intermediates was tested against HCT-8, BEL-7402, KETR3, HELA, BGC-823, KB and MCF-7 cell lines by the MTT test, and compound 15 exhibited significant cytotoxicity in HELA and KB cell lines.
Wang, Sheng-Peng,Tong, Yuan-Feng,Wang, Dong-Mei,Wang, Nan,Yan, Zheng,Huang, Ping,Wu, Song
p. 1044 - 1046
(2014/08/18)

Simple, copper(I)-catalyzed oxidation of benzylic/allylic alcohols to carbonyl compounds: Synthesis of functionalized cinnamates in one pot
An environmentally benign [Cu(I)]-catalyzed oxidation of activated (benzylic/allylic) alcohols to the corresponding carbonyl compounds is presented. Interestingly, the reaction was also compatible with benzylic alcohols containing ortho-bromo substituents on the aromatic ring without competing with the expected intermolecular Buchwald coupling. Significantly, the catalytic system enables the synthesis of cinnamate-esters in a sequential domino one-pot fashion via oxidation followed by Wittig-Horner protocol. Copyright
Reddy, Alavala Gopi Krishna,Mahendar, Lodi,Satyanarayana, Gedu
supporting information
p. 2076 - 2087
(2014/07/07)

A high-yielding modular access to the lamellarins: Synthesis of lamellarin G trimethyl ether, lamellarin η and dihydrolamellarin η
A deprotonated α-aminonitrile serves as a key intermediate in a highly efficient (95 % per step on average; see scheme) modular synthetic approach to the lamellarin alkaloids. Its reaction with an α,β- unsaturated aldehyde forms the central pyrrole ring in a one-pot procedure. The construction of the fused pentacyclic skeleton is completed by a microwave-assisted Ullmann-type lactone formation.
Imbri, Dennis,Tauber, Johannes,Opatz, Till
supporting information
p. 15080 - 15083
(2013/11/06)

ARYL NAPHTHALIDE LIGNANS AS ANTI-HIV AGENTS
Provided herein are glycosidic aryl naphthalide lignans compounds, such as justiprocumin A isolated from the plant Justicia gendarussa Burm.f. (Acanthaceae), which are effective in the treatment of AIDS and HIV infections.
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Paragraph 0067

(2013/03/26)

Synthesis, topoisomerase-targeting activity and growth inhibition of lycobetaine analogs
The plant alkaloid lycobetaine has potent topoisomerase-targeting properties and shows anticancer activity. Based on these findings, several lycobetaine analogs were synthesized mainly differing in their substituents at 2, 8 and 9 position and their biological activities were evaluated. The topoisomerase-targeting properties and cytotoxicity of these structural analogs were assessed in the human gastric carcinoma cell line GXF251L. Performing a plasmid relaxation assay, an increased inhibition of topoisomerase I was found with N-methylphenanthridinium chlorides bearing a 8,9-methylenedioxy moiety or a methoxy group in 2-position. Furthermore, quaternized phenanthridinium derivatives bearing either a 2-methoxy or a 8,9-methylenedioxy moiety in conjunction with a 2-hydroxy or 2-methoxy group display potent topoisomerase II inhibition as shown by decatenation of kinetoplast DNA. In general, the N-methylphenanthridinium chlorides possess more potency in inhibiting topoisomerase I than topoisomerase II. All quaternized derivatives also exhibited potent inhibition of tumor cell growth in the low micromolar concentration range. Hence, N-methylphenanthridinium compounds were found to represent a promising class of compounds, potently inhibiting both, topoisomerases I and II, and may be further developed into clinically useful topoisomerase inhibitors.
Baechler, Simone A.,Fehr, Markus,Habermeyer, Michael,Hofmann, Andreas,Merz, Karl-Heinz,Fiebig, Heinz-Herbert,Marko, Doris,Eisenbrand, Gerhard
supporting information
p. 814 - 823
(2013/02/25)

Syntheses of 3,4-benzotropolones by ring-closing metatheses
Ortho-lithiated styrenes or ortho-lithiated benzaldehyde dimethyl acetals were added to 2,2-dimethoxypent-4-enals 7. The resulting alcohols were carried on to the aromatic dienones 10. These were ring-closed by olefin metathesis. Hydrolysis of the dimethyl ketal moiety and enolization provided the 3,4-benzotropolones 5. Overall, this access comprises 4-6 steps and totaled a 22-81% yield.
Arican, Deniz,Brückner, Reinhard
supporting information
p. 2582 - 2585
(2013/07/19)

PROCESS FOR PRODUCTION OF OXIDATION REACTION PRODUCT OF AROMATIC COMPOUND
The present invention provides a process for producing an oxidation reaction product of an aromatic compound, having excellent environmental load reduction performance, cost reduction performance, etc. Provided is a process for producing an oxidation reaction product of a raw material aromatic compound by reacting the raw material aromatic compound with an oxidizing agent. The process further uses an electron donor-acceptor linked molecule. The process includes the step of: reacting the electron donor-acceptor linked molecule in an electron-transfer state, the oxidizing agent, and the raw material aromatic compound, thereby generating an oxidation reaction product resulting from oxidation of the raw material aromatic compound.
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(2012/07/14)

Total synthesis of 60-hydroxyjusticidin A
The first total synthesis of 6′-hydroxyjusticidin A, isolated from Justicia procumbens L. with good inhibitory activity against cancer cells, has been accomplished. The structure was confirmed by 1H NMR, 13C NMR, and HR-ESI-MS. The key steps involved a Diels-Alder cycloaddition reaction and a reduction in NaBH4.
Xiong, Lu,Bi, Ming-Gang,Wu, Song,Tong, Yuan-Feng
scheme or table
p. 322 - 326
(2012/08/28)

PROCESS FOR THE SYNTHESIS OF CLEISTANTHIN
The present invention relates to a process for preparing compound of formula (I) that is Cleistanthin A. The process comprises the steps of reacting compound of formula (II) with compound of formula (III) in the presence of a first solvent, quarternary ammonium salt and first alkali to form compound of formula (IV). The compound of formula (IV) is further treated with a second solvent and a second alkali to form compound of formula (I). The present invention also relates to the preparation of salt of compound of formula (IV) that is Cleistanthin A acetate.
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(2012/02/06)

Tricyclic isoindolines by Heck cyclization
A series of 4-formyl esters 8a-d was prepared by Michael addition of an enamine with ethyl acrylate. A subsequent condensation with 2-bromobenzylamines 3 gave rise to cyclic enamides 9aa-dd. In a Heck cyclization reaction tricyclic isoindoles 10aa-dd were formed in good yields.
Satyanarayana, Gedu,Maier, Martin E.
scheme or table
p. 1745 - 1749
(2012/03/10)

Aromatic bromination of aldehydes and ketones using 1,3-di-n- butylimidazolium
An environmentally benign and efficient process for the preparation of monobromo derivatives of aryl aldehydes and ketones was developed by simple and practical reactions of aryl aldehydes or ketones with 1,3-di-n-butylimidazolium tribromide ([BBIm]Br3), as a brominating reagent under solvent-free conditions in very high yields. The process has several advantages: high conversions, short reaction time, mild reaction conditions, simple workup with good to quantitative yields and re-usable ionic liquid.
Borikar,Daniel
experimental part
p. 531 - 536
(2012/07/01)

Facile total synthesis of benzo[b]furan natural product XH-14
An efficient and practical total synthesis of benzo[b]furan natural product XH-14 is demonstrated in nine steps from vanillin. Introduction of iodide substituents in the reaction including optimization of the reaction sequences is essential for the successful synthesis of XH-14. Sonogashira coupling with iodobenzene, iodine-induced cyclization, Wittig reaction, and formylation are critical in the high-yield total synthesis of XH-14. Copyright Taylor & Francis Group, LLC.
Bang, Hyun Bae,Han, Su Young,Choi, Da Hye,Yang, Deok Mo,Hwang, Jung Woon,Lee, Hyun Suck,Jun, Jong-Gab
body text
p. 506 - 515
(2009/06/28)

A practical synthesis of 1-cyano-4,5-dimethoxybenzocyclobutene
A practical synthesis of 1-cyano-4,5-dimethoxybenzocyclobutene, the key intermediate of Ivabradine, was developed in four or five steps using two different routes. 2-Bromo-4,5-dimethoxyhydrocinnamonitrile was produced via the condensation of 2-bromo-4,5-dimethoxybenzaldehyde with acetonitrile or cyanoacetic acid and reduction by NaBH4. Cyclisation gave 1-cyano-4,5-dimethoxybenzocyclobutene. Overall yields of the routes A and B were 30% and 37% respectively. Route B is a short and simple route, permitting the synthesis of 1-cyano-4,5-dimethoxybenzocyclobutene on a large scale.
Zhao, Sheng Yin,Liang, Hong Yu,Shao, Zhi Yu,Chen, Rui
experimental part
p. 420 - 422
(2010/01/16)

Gold-catalyzed deoxygenative Nazarov cyclization of 2,4-dien-1-als for stereoselective synthesis of highly substituted cyclopentenes
Treatment of 2,4-dien-1-als with allylsilanes and PPh3AuSbF 6 (3 mol %) led to formation of 1,4-bis(allyl)cyclopentenyl products; this gold catalyst is superior to commonly used Lewis acids according to catalyst screening. Such gold-catalyzed deoxygenative cyclizations are compatible with various oxygen-, amine-, sulfur-, hydrogen-, and carbon-based nucleophiles. The value of this new catalysis is demonstrated by the diverse annulations of 2,4-dien-1-als with electron-rich alkenes and arenes, providing an easy access to complicated cyclopentenyl frameworks. Structural analysis of annulation products reveals evidence for the participation of Nazarov cyclization. This deoxygenative cyclization is extensible to a tandem intramolecular cyclization/nucleophilic addition cascade, giving polycyclic carbo- or oxacyclic compounds with controlled stereochemistry. This new gold catalysis is applied to a short synthesis of natural compounds of the brazilane family, including brazilane, O-trimethyl-, and O-tetramethyl brazilane.
Lin, Chung-Chang,Teng, Tse-Min,Tsai, Chung-Chih,Liao, Hsin-Yi,Liu, Rai-Shung
supporting information; scheme or table
p. 16417 - 16423
(2009/05/09)

OPTICALLY ACTIVE CYCLIC ALCOHOL COMPOUND AND METHOD FOR PRODUCING SAME
Disclosed is a method for producing an optically active cyclic alcohol compound represented by the general formula [I] below, wherein a cyclic ketone compound represented by the general formula [II] below is asymmetrically reduced in the presence of (A) an optically active oxazaborolidine compound and a boron hydride compound, or alternatively in the presence of (B) an asymmetric transition metal complex obtained from a transition metal compound and an asymmetric ligand, and a hydrogen donor. Also disclosed is such an optically active cyclic alcohol compound. [I] (In the formula, the symbol is as defined below.) [II] (In the formula, R represents a hydrogen atom or a protective group of an amino group.)
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(2010/11/26)

Photoinduced C-Br homolysis of 2-bromobenzophenones and Pschorr ring closure of 2-aroylaryl radicals to fluorenones
(Chemical Equation Presented) A variety of diversely substituted 2-aroylaryl radicals, generated by photoinduced homolysis of 2-bromoarylketones, is shown to undergo Pschorr cyclization to yield fluorenones in moderate to excellent yields. The photochemical results illustrate that the substituents in the two phenyl rings of the 2-bromobenzophenone skeleton exert a dramatic influence on the reactivity of the derived 2-aroylaryl radicals. The disubstitution by methoxy groups in the radical ring renders the aryl σ-radical highly electrophilic and unreactive for hydrogen abstraction and cyclization. On the other hand, the substituents in the non-radical ring that strongly stabilize the hydrofluorenyl π-radical, formed subsequent to the attack of the 2-aroylaryl radical on the non-radical ring, promote cyclization to furnish fluorenones in excellent isolated yields.
Moorthy, Jarugu Narasimha,Samanta, Subhas
p. 9786 - 9789
(2008/03/17)

Microwave-assisted transition-metal-catalyzed synthesis of N-shifted and ring-expanded buflavine analogues
Two novel and efficient strategies for the synthesis of hitherto unknown N-shifted and ring-expanded buflavine analogues are presented. Construction of the medium-sized ring system of the title molecules, a difficult task due to the high activation energy needed for the ring-closure with the additional rigidity imposed by the biaryl skeleton, was achieved by using Suzuki-Miyaura biaryl coupling and a ring-closing metathesis reaction as the key steps. The combination of a second-generation Grubbs catalyst and microwave irradiation proved to be highly useful in generating the otherwise difficult to obtain medium-sized ring system of the buflavine analogues.
Appukkuttan, Prasad,Dehaen, Wim,Van Der Eycken, Erik
p. 6452 - 6460
(2008/02/13)

Synthetic studies on Ecteinascidin-743: synthesis of building blocks through Sharpless asymmetric dihydroxylation and aza-Michael reactions
A practical and an efficient synthesis of three building blocks of tetrahydroisoquinoline alkaloid Ecteinascidin-743 was accomplished, starting from readily available piperonal, 2-methyl anisole, and veratraldehyde. A combination of Vilsmeier-Haack reaction and Sharpless asymmetric dihydroxylation was employed for the synthesis of building blocks A and B whereas a Heck reaction in PEG-2000 and aza-Michael reactions were employed for the synthesis of building block C.
Chandrasekhar,Reddy, N. Ramakrishna,Rao, Y. Srinivasa
p. 12098 - 12107
(2007/10/03)

Total synthesis of antofine using the net [5+5]-cycloaddition of γ,δ-unsaturated carbene complexes and 2-alkynylphenyl ketones as a key step
A compound containing all of the carbons of the anticancer agent antofine was produced in a single step from the coupling of a γ,δ-unsaturated carbene complex with a 2-alkynylphenyl ketone derivative. Subsequent conversion to antofine was effected in three steps.
Camacho-Davila, Alejandro,Herndon, James W.
p. 6682 - 6685
(2007/10/03)

Intermolecular silyl migration reactions
Sodium hydride promoted O-alkylation of 2-[(4-t-butyldimethylsilyloxy) phenyl]ethan-1-ol with 1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene depend on the solvent used in the coupling reaction. Mixtures of 2-[4-(2-bromo-4,5- dimethoxybenzyloxy)phenyl]-1-t-butyldimethylsilyloxyethaneand2-[4-(2-bromo-4, 5-dimethoxybenzyloxy)phenyl] ethan-1-ol (in DMF), or 2-[4-(2-bromo-4,5- dimethoxybenzyloxy)phenyl]-1-t-butyldimethylsilyloxyethane and 4-[2-(2-bromo-4,5-dimethoxybenzyloxy)ethyl]phenol (in THF), were detected. These results can be explained by an unusual intermolecular silyl migration reaction.
Rodriguez, Carolina,Garcia, Antonio G.,Marco-Contelles, Jose
p. 698 - 701
(2007/10/03)

PROCESS FOR PREPARATION OF BENZAZEPINE
This invention discloses a process for manufacture of galanthamine, which involves a stereoselective reduction step to get the desired isomer of galanthamine. The current embodiment also discusses the method for improving the chiral and chemical purity of galanthamine and galanthamine salts.
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(2008/06/13)

Microwave-enhanced synthesis of N-shifted buflavine analogues via a Suzuki-ring-closing metathesis protocol
(Chemical Equation Presented) A novel, microwave-enhanced six-step synthesis was devised for the synthesis of N-shifted buflavine analogues. Microwave-enhanced Suzuki-Miyaura cross-coupling and ring-closing metathesis reactions were used as the key steps. Microwave irradiation was found to enhance the ring-closing metathesis reaction to generate the otherwise difficultly obtainable medium-sized ring system of the target molecules.
Appukkuttan, Prasad,Dehaen, Wim,Van Der Eycken, Erik
p. 2723 - 2726
(2007/10/03)