- N-ALKYL-N-CYANOALKYLBENZAMIDE COMPOUND AND USE THEREOF
-
The present invention discloses an N-alkyl-N-cyanoalkylbenzamide compound of General Formula I, an intermediate of General Formula II used to prepare the compound, wherein R1 is selected from halo or C1-C3 alkyl; R2
- -
-
Paragraph 0039; 0041-0042
(2021/01/25)
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- Divergent Syntheses of Indoles and Quinolines Involving N1-C2-C3 Bond Formation through Two Distinct Pd Catalyses
-
Pd-catalyzed annulative couplings of 2-alkenylanilines with aldehydes using alcohols as both the solvent and hydrogen source have been developed. These domino processes allow divergent syntheses of two significant N-heterocycles, indoles and quinolines, from the same substrate by tuning reaction parameters, which seems to invoke two distinct mechanisms. The nature of the ligand and alcoholic solvent had a profound influence on the selectivity and efficiency of these protocols. Particularly noteworthy is that indole formation was achieved by overcoming two significant challenges, regioselective hydropalladation of alkenes and subsequent reactions between the resulting Csp3-Pd species and less reactive imines.
- San Jang, Su,Kim, Young Ho,Youn, So Won
-
p. 9151 - 9157
(2020/11/03)
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- AZABICYCLO AND DIAZEPINE DERIVATIVES FOR TREATING OCULAR DISORDERS
-
The present invention provides in one aspect azabicycio and diazepine derivatives useful as modulators of muscarinic receptors. In another aspect, the present invention provides pharmaceutical compositions for treating ocular diseases, the compositions comprising at least one muscarinic receptor modulator. Formulae (I) & (II):
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Page/Page column 70
(2019/05/22)
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- BENZOCARBONYL COMPOUNDS
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Provided herein are compounds and pharmaceutical compositions comprising said compounds that are useful for treating cancers. Specific cancers include those that are mediated by YAP/TAZ or those that are modulated by the interaction between YAP/TAZ and TEAD.
- -
-
Paragraph 00497
(2019/06/23)
-
- Method for preparing 2-amino-4'-fluorobenzophenone
-
The invention discloses a method for preparing 2-amino-4'-fluorobenzophenone. The method comprises the following steps: o-nitrotoluene, trichloroisocyanuric acid, tetramethylpiperidine nitrogen oxideand sodium bromide undergo an oxidation reaction to obtain o-nitrobenzoic acid; the o-nitrobenzoic acid and trichloromethyl carbonate undergo an acylating chlorination to obtain o-nitrobenzoyl chloride; the o-nitrobenzoyl chloride, fluorobenzene and aluminum trichloride undergo a Friedel-Crafts reaction to obtain 2-nitro-4'-fluorobenzophenone; and the 2-nitro-4'-fluorobenzophenone is reduced by hydrogen to the 2-amino-4'-fluorobenzophenone. The method has the advantages of green and environmentally-friendly synthesis route, cheap and easily available initial raw materials, low cost, convenience in operation, suitableness for industrial production, and high yield, and the prepared 2-amino-4'-fluorobenzophenone has a good purity.
- -
-
-
- Synthesis, characterization and microbial activity of new aryl esters of 1,1'-bis(4-hydroxyphenyl)cyclohexane
-
Aryl esters of 1,1'-bis(4-hydroxyphenyl)cyclohexane (bisphenol-C) were synthesized by condensing bisphenol-C with aryl acid chlorides using triethylamine as a catalyst and ethyl acetate as a solvent at room temperature.The compounds were characterized by
- Patel, Chirag Bhupendra,Dhaduk, Bhavin Babu,Parsania, Parsotam Hari
-
p. 505 - 511
(2015/06/22)
-
- Synthesis and Quantitative Structure-Activity Relationships of Selective BCRP Inhibitors
-
The breast cancer resistance protein (BCRP/ABCG2) is a member of the ABC transporter superfamily. This protein has a number of physiological functions, including protection of the human body from xenobiotics. The overexpression of BCRP in certain tumor cell lines causes cross-resistance against various drugs used in chemotherapeutic treatment. In a previous work we showed that a new class of compounds derived from XR9576 (tariquidar) selectively inhibits BCRP. In this work we synthesized more members of this class, with modification on the second and third aromatic rings. The inhibitory activities against BCRP and P-gp were assayed using a Hoechst 33342 assay for BCRP and a calcein AM assay for P-gp. Finally, quantitative structure-activity relationships for both aromatic rings were established. The results obtained show the importance of the electron density on the third aromatic ring, influenced by substituents, pointing to interactions with aromatic residues of the protein binding site. In the second aromatic ring the activity of compounds is influenced by the steric volume of the substituents.
- Marighetti, Federico,Steggemann, Kerstin,Hanl, Markus,Wiese, Michael
-
p. 125 - 135
(2013/02/26)
-
- A class of 5-nitro-2-furancarboxylamides with potent trypanocidal activity against Trypanosoma brucei in vitro
-
Recently, the World Health Organization approved the nifurtimox- eflornithine combination therapy for the treatment of human African trypanosomiasis, renewing interest in nitroheterocycle therapies for this and associated diseases. In this study, we have synthesized a series of novel 5-nitro-2-furancarboxylamides that show potent trypanocidal activity, ~1000-fold more potent than nifurtimox against in vitro Trypanosoma brucei with very low cytotoxicity against human HeLa cells. More importantly, the most potent analogue showed very limited cross-resistance to nifurtimox-resistant cells and vice versa. This implies that our novel, relatively easy to synthesize and therefore cheap, 5-nitro-2-furancarboxylamides are targeting a different, but still essential, biochemical process to those targeted by nifurtimox or its metabolites in the parasites. The significant increase in potency (smaller dose probably required) has the potential for greatly reducing unwanted side effects and also reducing the likelihood of drug resistance. Collectively, these findings have important implications for the future therapeutic treatment of African sleeping sickness.
- Zhou, Linna,Stewart, Gavin,Rideau, Emeline,Westwood, Nicholas J.,Smith, Terry K.
-
supporting information
p. 796 - 806
(2013/03/28)
-
- Carboxamide versus sulfonamide in peptide backbone folding: A case study with a hetero foldamer
-
Strikingly dissimilar hydrogen-bonding patterns have been observed for two sets of closely similar hetero foldamers containing carboxamide and sulfonamides at regular intervals. Although both foldamers maintain conformational ordering, the hydrogen-bondin
- Ramesh, Veera V. E.,Kale, Sangram S.,Kotmale, Amol S.,Gawade, Rupesh L.,Puranik, Vedavati G.,Rajamohanan,Sanjayan, Gangadhar J.
-
supporting information
p. 1504 - 1507
(2013/06/27)
-
- New quinazoline derivatives for telomeric G-quadruplex DNA: Effects of an added phenyl group on quadruplex binding ability
-
To improve the selectivity of indoloquinoline or benzofuroquinoline derivatives, we previously reported several quinazoline derivatives [17]. These compounds could mimic a tetracyclic aromatic system through intramolecular hydrogen bond. Studies showed that these quinazoline derivatives were effective and selective telomeric G-quadruplex ligands. With this encouragement, here we synthesized a series of N-(2-(quinazolin-2-yl)phenyl)benzamide (QPB) compounds as modified quinazoline derivatives. In this modification, a phenyl group was introduced to the aromatic core. The evaluation results showed that part of QPB derivatives had stronger binding ability and better selectivity for telomeric G-quadruplex DNA than LZ-11, the most potential compound of reported quinazoline derivatives. Furthermore, telomerase inhibition of QPB derivatives and their cellular effects were studied.
- He, Jin-Hui,Liu, Hui-Yun,Li, Zeng,Tan, Jia-Heng,Ou, Tian-Miao,Huang, Shi-Liang,An, Lin-Kun,Li, Ding,Gu, Lian-Quan,Huang, Zhi-Shu
-
-
- ANTIVIRAL COMPOUNDS
-
The present invention provides new antiviral compounds and pharmacological compositions comprising these new compounds and their use in the prophylaxis, prevention and treatment of viral infections, particularly adenovirus and herpes virus infections.
- -
-
Paragraph 0242; 0243; 0244; 0245
(2013/08/28)
-
- Synthesis, biological evaluation, and structure-activity relationships of 2-[2-(benzoylamino)benzoylamino]benzoic acid analogues as inhibitors of adenovirus replication
-
2-[2-Benzoylamino)benzoylamino]benzoic acid (1) was previously identified as a potent and nontoxic antiadenoviral compound (Antimicrob. Agents Chemother. 2010, 54, 3871). Here, the potency of 1 was improved over three generations of compounds. We found that the ortho, ortho substituent pattern and the presence of the carboxylic acid of 1 are favorable for this class of compounds and that the direction of the amide bonds (as in 1) is obligatory. Some variability in the N-terminal moiety was tolerated, but benzamides appear to be preferred. The substituents on the middle and C-terminal rings were varied, resulting in two potent inhibitors, 35g and 35j, with EC50 = 0.6 μM and low cell toxicity.
- ?berg, Christopher T.,Strand, M?rten,Andersson, Emma K.,Edlund, Karin,Tran, Nam Phuong Nguyen,Mei, Ya-Fang,Wadell, G?ran,Elofsson, Mikael
-
experimental part
p. 3170 - 3181
(2012/06/04)
-
- Cyclisation of 2-(2-aminophenyl)quinazolin-4(3H)-one reexamined: Formation of isomeric angular fused quinazolinoquinazolinones and their spectroscopic identification
-
Cyclisation of 2-(2-aminophenyl)quinazolin-4(3H)-ones on to N3 and on to N1 leading to 6-alkyl-(8H)-quinazolino[4,3-b]quinazolin-8- one and 6-alkyl-(13H)-quinazolino[3,4-a]quinazolin-13-one, respectively was described for the first time. The differences in the IR and carbon NMR data of these isomeric fused quinazolinoquinazolinones afford a useful method for distinguishing between the two series.
- Venkateswarlu, Somepalli,Satyanarayana, Meka,Murthy, Gandrothu Narasimha,Siddaiah, Vidavalur
-
scheme or table
p. 2643 - 2646
(2012/06/30)
-
- Synthesis, antimicrobial evaluation, and QSAR analysis of 2-isopropyl-5-methylcyclohexanol derivatives
-
A series of 2-isopropyl-5-methylcyclohexanol derivatives were synthesized and evaluated for their antibacterial activity against Gram-positive Staphylococcus aureus and Bacillus subtilis and Gram-negative Escherichia coli and in vitro antifungal activity against Candida albicans and Aspergillus niger. The results of antimicrobial activity demonstrated that the compounds 10, 20, and 21 were the most active ones among the synthesized compounds. The QSAR studies revealed the importance of dipole moment (μ), total energy (Te), and topological parameters (κ1 and κ3) in describing the antimicrobial activity of 2-isopropyl-5-methylcyclohexanol derivatives. Springer Science+Business Media, LLC 2011.
- Singh, Manjeet,Kumar, Sunil,Kumar, Ashwani,Kumar, Pradeep,Narasimhan, Balasubramanian
-
experimental part
p. 511 - 522
(2012/08/07)
-
- Synthesis and evaluation of boronic acids as inhibitors of Penicillin Binding Proteins of classes A, B and C
-
In response to the widespread use of β-lactam antibiotics bacteria have evolved drug resistance mechanisms that include the production of resistant Penicillin Binding Proteins (PBPs). Boronic acids are potent β-lactamase inhibitors and have been shown to display some specificity for soluble transpeptidases and PBPs, but their potential as inhibitors of the latter enzymes is yet to be widely explored. Recently, a (2,6-dimethoxybenzamido) methylboronic acid was identified as being a potent inhibitor of Actinomadura sp. R39 transpeptidase (IC50: 1.3 μM). In this work, we synthesized and studied the potential of a number of acylaminomethylboronic acids as inhibitors of PBPs from different classes. Several derivatives inhibited PBPs of classes A, B and C from penicillin sensitive strains. The (2-nitrobenzamido)methylboronic acid was identified as a good inhibitor of a class A PBP (PBP1b from Streptococcus pneumoniae, IC50 = 26 μM), a class B PBP (PBP2xR6 from Streptococcus pneumoniae, IC50 = 138 μM) and a class C PBP (R39 from Actinomadura sp., IC50 = 0.6 μM). This work opens new avenues towards the development of molecules that inhibit PBPs, and eventually display bactericidal effects, on distinct bacterial species.
- Zervosen, Astrid,Bouillez, Andre,Herman, Alexandre,Amoroso, Ana,Joris, Bernard,Sauvage, Eric,Charlier, Paulette,Luxen, Andre
-
experimental part
p. 3915 - 3924
(2012/08/28)
-
- Synthesis and cytotoxic activity of 2,5-disubstituted pyrimido[5,4-c] quinoline derivatives
-
A series of 2,5-disubstituted pyrimido[5,4-c]quinoline derivatives were synthesized and their cytotoxic activity against H460, HT-29 and MDA-MB-231 cell lines was evaluated in vitro. It was found that most of the tested compounds especially compound 17, s
- Zhang, Fan,Zhai, Xin,Chen, Li Juan,Qi, Jian Guo,Cui, Bo,Gu, Yu Cheng,Gong, Ping
-
scheme or table
p. 1277 - 1280
(2012/01/06)
-
- NEW ANTIVIRAL COMPOUNDS
-
The present invention provides new antiviral compounds and pharmacological compositions comprising these new compounds and their use in the prophylaxis, prevention and treatment of viral infections, particularly adenovirus and herpes virus infections.
- -
-
Page/Page column 36
(2012/01/05)
-
- Silver-and gold-mediated domino transformation: A strategy for synthesizing benzo[ e ]indolo[1,2-a ]pyrrolo/pyrido[2,1-c ][1,4]diazepine-3,9-diones
-
We reported a strategy for the synthesis of fused heterocyclic compounds benzo[e]indolo[1,2-a]pyrrolo/pyrido[2,1-c][1,4]diazepine-3,9-diones via an AgSbF6/gold-complex catalyzed one-pot cascade transformation. The strategy is tolerant of a broad range of substrates and affords a series of intriguing fused diazepinedione heterocycles.(Figure Presented)
- Zhou, Yu,Li, Jian,Ji, Xun,Zhou, Wei,Zhang, Xu,Qian, Wangke,Jiang, Hualiang,Liu, Hong
-
experimental part
p. 1239 - 1249
(2011/04/26)
-
- Synthesis of 2-amino-1,4-benzodiazepin-5-ones from 2-nitrobenzoic acid and α-aminonitriles
-
Condensation of α-aminonitriles with 2-nitrobenzoyl chloride gives the corresponding Schiff bases, which furnish, upon reduction with Zn, the corresponding 2-amino-3,4-dihydro-5H-l,4- benzodiazepin-5-ones. However, reduction of the Schiff base obtained fr
- Younes, Eyad A.,Hussein, Ahmad Q.,May, Mitchell A.,Fronczek, Frank R.
-
scheme or table
p. 322 - 330
(2011/05/19)
-
- The synthesized novel fluorinated compound (LJJ-10) induces death receptor- and mitochondria-dependent apoptotic cell death in the human osteogenic sarcoma U-2 OS cells
-
We designed the 6-fluoro-2-(3-fluorophenyl)-4-substituted anilinoquinazoline derivatives as less toxic anti-cancer candidates. Our result demonstrated that LJJ-10 has greater cytotoxicity than that of the other compounds in human osteogenic sarcoma U-2 OS cells. LJJ-10-induced apoptosis was associated with enhancing ROS generation, DNA damage, and an increase of the protein levels of Fas, FasL, FADD, caspase-8, cytochrome c, Apaf-1, AIF, Endo G, caspase-9 and caspase-3 in U-2 OS cells. LJJ-10-triggered growth inhibition was significantly attenuated by N-acetylcysteine, cyclosporine A, anti-FasL monoclonal antibody, and caspase-8, -9 and -3 specific inhibitors in U-2 OS cells. We suggest that LJJ-10-induced apoptotic cell death in U-2 OS cells through death receptor- and mitochondria-dependent apoptotic signaling pathways.
- Hour, Mann-Jen,Yang, Jai-Sing,Chen, Tai-Lin,Chen, Kuan-Tin,Kuo, Sheng-Chu,Chung, Jing-Gung,Lu, Chi-Cheng,Chen, Chia-Yi,Chuang, Yi-Hsuan
-
experimental part
p. 2709 - 2721
(2011/06/27)
-
- Synthesis and fungicidal activity of 1,3-thiazoline derivatives bearing nitrophenyl group on the 2-position
-
Ortho-, meta-, or para-nitro benzoic acid were refluxed with excess SOCl2 to give acyl chloride, which condensed with β-amino alcohol in the presence of Et3N in dichloromethane to afford β-hydroxyamide; finally, sulphonation and cycl
- Zhao, Qiuying,Li, Jing,Yan, Xiaojing,Yuan, Huizhu,Qin, Zhaohai,Fu, Bin
-
experimental part
p. 729 - 732
(2011/07/31)
-
- Metal-free intramolecular oxidative decarboxylative amination of primary α-amino acids with product selectivity
-
A novel metal-free intramolecular oxidative decarboxylative coupling of primary α-amino acids with 2-aminobenzoketones under mild and neutral conditions was developed. Different quinazolines can be selectively obtained by various oxidants.
- Yan, Yizhe,Wang, Zhiyong
-
supporting information; experimental part
p. 9513 - 9515
(2011/10/01)
-
- METHODS FOR PREPARING AMIDE DERIVATIVES
-
The present invention provides a novel method for preparing an amide derivative. The method of the present invention enables to economically prepare various amide derivatives containing pranlukart by reacting a carboxylic acid derivative 5 and an amine derivative through a brief procedure compared with a conventional technology, and permits to obtain a final product at a high yield rate because it is feasible to eliminate by-products after termination of reactions. Accordingly, the present method is to be quite suitable for massive production.
- -
-
Page/Page column 26-27
(2010/04/03)
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- A simple and efficient approach to the synthesis of 2-phenylquinazolines via sp3 C-H functionalization
-
(Figure presented) A facile and novel approach to the synthesis of 2-phenylquinazolines was developed via a tandem reaction following sp 3 C-H functionalization. Twenty-five examples of 2-phenylquinazolines were obtained from easily available 2-aminobenzophenones and benzylic amines with good to excellent yields.
- Zhang, Jintang,Zhu, Dapeng,Yu, Chenmin,Wan, Changfeng,Wang, Zhiyong
-
supporting information; experimental part
p. 2841 - 2843
(2010/09/04)
-
- A novel and efficient methodology for the construction of quinazolines based on supported copper oxide nanoparticles
-
A series of quinazolines were synthesized from 2-aminobenzophenones and benzylic amines in good to excellent yields by employing a new heterogeneous catalyst based on the copper oxide nanoparticles supported on kaolin.
- Zhang, Jintang,Yu, Chenmin,Wang, Sujing,Wan, Changfeng,Wang, Zhiyong
-
supporting information; experimental part
p. 5244 - 5246
(2010/09/05)
-
- Novel approach to synthesis of substituted 3-aminoquinolines from nitroarenes and protected ethyl aminocrotonate
-
The addition of mono- and dianions of ethyl N-pivaloyl-3-aminocrotonate to substituted nitroarenes, followed by action of silylating or acylating agent, leads to 3-aminoquinoline carboxylic acid derivatives. Hydrolysis and decarboxylation of the latter, carried out efficiently under relatively mild conditions, afford 3-aminoquinolines diversely substituted in the benzo-fused ring.
- Bujok, Robert,Kwast, Andrzej,Cmoch, Piotr,Wróbel, Zbigniew
-
experimental part
p. 698 - 708
(2010/09/05)
-
- Conformational studies of tertiary oligo-m-benzanilides and oligo-p-benzanilides in solution
-
A series of oligo-m- and p-benzanilides were made and their conformations in solution were studied by NMR. In most cases, conformational mixtures were observed as soon as three or more monomers were incorporated into the oligomer. Some crystal structures were obtained, which indicated that helical conformations were adopted in the solid state.
- Chabaud, Laurent,Clayden, Jonathan,Helliwell, Madeleine,Page, Abigail,Raftery, James,Vallverdú, Lluís
-
experimental part
p. 6936 - 6957
(2010/10/02)
-
- Study on the structure-activity relations of pleuromutilin derivatives with an aromatic amide and a thioether group in the C14 side chain
-
Nine novel pleuromutilin derivatives having benzamide substituents have been synthesised permitting structureactivity relations of pleuromutilin derivatives with aromatic amide and thioether groups in the C14 side chain to be studied. The results showed that the heterocyclic carboxamide group was necessary to enhance bio-activities.
- Xu, Ke-Ping,Zhang, Yuan-Yuan,Luo, Juan,Chen, Shan-Li,Wang, Yu-Liang
-
experimental part
p. 354 - 357
(2010/10/21)
-
- Novel 4- and 7-sulfonylated 2-substituted benzoxazoles
-
The efficient synthesis of sulfonylated benzoxazoles at positions C 4 or C7 is reported. The condensation reactions involve original anilide acetal reagents which, upon acid catalysis, allow an easy cyclization reaction with the sulfonylated o-aminophenol partners. This method circumvents the classical use of orthoesters which drawback is the limited access to aromatic reagents. Georg Thieme Verlag Stuttgart.
- Bruyneel, Frédéric,Marchand-Brynaert, Jacqueline
-
supporting information; experimental part
p. 1974 - 1978
(2010/10/03)
-
- N-aroylated isatins: Antiglycation activity
-
A series of N-aroylated isatins 1-15 was synthesized and evaluated for their antiglycation activity. All compounds showed a varying degree of glycation inhibitory activity with IC50 values between 18.01 ± 0.05-693.7 ± 3.0 μM, when compared with the standard (aminoguanidine) having an IC50 = 268.7 ± 12.4 μM. Compound 1 was found to be the most active member of this series with an IC50 = 18.01 ± 0.05 μM. Compound 10 showed an IC50 = 72.5 ± 0.09 μM, whereas compound 7 has an IC50 = 80.18 ± 0.07 μM. Compounds 3, 9, and 13 showed IC50 values 170.2 ± 0.62, 117.91 ± 2.9, 171.3 ± 0.79 μM, respectively. Rest of the compounds along with parent isatin were found to be inactive. The structures of all the synthetic compounds were deduced by spectroscopic analysis.
- Khan, Khalid Mohammed,Mughal, Uzma Rasool,Khan, Ambreen,Naz, Farzana,Perveen, Shahnaz,Choudhary, M. Iqbal
-
scheme or table
p. 188 - 193
(2011/02/21)
-
- Efficient synthesis of naturally occurring skeleton 5-7-6 tricyclic pyrrolo[2,1- c ][1,4]benzodiazepin-5-one and its derivatives via cationic π-cyclization
-
An efficient method for the synthesis of a library based on the naturally occurring 5-7-6 tricyclic 5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one skeleton and its derivatives via cationic π-(7-endo) cyclization is described. Georg Thieme Verlag Stuttgart - New York.
- Sharma, Sudhir K.,Mandadapu, Anil K.,Kumaresan,Arora, Ashish,Gauniyal, Harsh M.,Kundu, Bijoy
-
supporting information; experimental part
p. 4087 - 4095
(2011/02/22)
-
- The synthesis of N-phenoxyethyl-1-substituted-1,2,3,4-tetrahydroisoquinolines and their α1-adrenoceptor blocking activity
-
A series of phenoxyisoquinolines, N-phenoxyethyl-1-(2-nitrophenyl)-1,2,3,4-THIQs 3a-3d, N-phenoxyethyl-1-benzyl-1,2,3,4-THIQ 3e, N-phenoxyethyl-1-(2-aminophenyl)-1,2,3,4-THIQs 5f-5i, N-phenoxyethyl-1-(2-phenoxyethylaminophenyl)-1,2,3,4-THIQs 5f′-5i′, have
- Kuo, Chen-Yuan,Wu, Ming-Jung
-
scheme or table
p. 1271 - 1277
(2009/09/30)
-
- A new and facile synthesis of rutaecarpine alkaloids
-
Relevant rutaecarpine analogues (1a-d) have been synthesized efficiently from the ring opened β-carboline derivatives (3a-d) as key intermediates. A unique one-pot reductive-cyclization as key reaction furnished the synthesis of rutaecarpine alkaloids in excellent yields. The key intermediates (3a-d) were prepared from tryptamine following acylation, Bischler-Napieralski cyclization, benzoylation, and oxidative cleavage of the exocyclic double bond. This new synthetic approach provides a facile access to rutaecarpine analogues with potent inhibitory effect on platelet aggregation.
- Lee, Chih-Shone,Liu, Cheng-Kuo,Cheng, Yen-Yao,Teng, Che-Ming
-
experimental part
p. 1047 - 1056
(2009/10/04)
-
- One-pot reductive-cyclization as key step for the synthesis of rutaecarpine alkaloids
-
The quinazolinocarboline alkaloids including rutaecarpine (1a), euxylophoricine A (1b), and euxylophoricine C (1c) have been synthesized efficiently from the ring opened β-carboline derivative as key intermediate by a one-pot reductive-cyclization reaction. The key intermediate was prepared from tryptamine (6) following Bischler-Napieralski cyclization, benzoylation, and oxidative cleavage of the exocyclic double bond.
- Lee, Chih-Shone,Liu, Cheng-Kuo,Chiang, Yuen-Lin,Cheng, Yen-Yao
-
p. 481 - 484
(2008/09/17)
-
- Cascade synthesis of 3-quinolinecarboxylic ester via benzylation/ propargylation-cyclization
-
(Chemical Equation Presented) Reactions of 2-amino-aryl alcohols with β-ketoesters catalyzed by a catalytic amout of FeCl3 via tandem benzylation-cyclization produce the corresponding 3-quinolinecarboxylic esters in good to high yields. Extending this methodology to propargylation- cyclization, 2-nitrophenyl propargyl alcohols with β-ketoesters catalyzed by FeCl3 and SnCl2 also produce the 4-alkyne-3- quinolinecarboxylic esters. The mechanistic details of this benzylation/ propargylation and cyclization cascade process are also discussed.
- Fan, Jinmin,Wan, Changfeng,Sun, Gaojun,Wang, Zhiyong
-
supporting information; scheme or table
p. 8608 - 8611
(2009/04/04)
-
- Conformationally driven asymmetric induction of a catalytic dendrimer
-
Nature-s catalysts promote the reactions necessary for life with extremely high specificity by folding into specific shapes capable of communicating remote structural information to an active site. Achieving this objective in synthetic systems has been ha
- Yu, Jianfeng,RajanBabu,Parquette, Jon R.
-
supporting information; scheme or table
p. 7845 - 7847
(2009/02/02)
-
- A practical, metal-free synthesis of 1H-Lndazoles
-
The synthesis of 1H-indazoles is achieved from o-aminobenzoximes by the selective activation of the oxime in the presence of the amino group. The reaction occurs with a variety of substituted o-aminobenzoximes using a slight excess of methanesulfonyl chloride and triethylamine at 0-23 °C and is amenable to scale-up. The synthesis of 1 H-indazoles under these conditions is extremely mild compared with previous synthetic approaches and affords the desired compounds in good to excellent yields.
- Counceller, Carla M.,Eichman, Chad C.,Wray, Brertda C.,Stambuli, James P.
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supporting information; experimental part
p. 1021 - 1023
(2009/04/07)
-
- Helix persistence and breakdown in oligoureas of metaphenylenediamine: Apparent diastereotopicity as a spectroscopic marker of helix length in solution
-
Oligomeric ureas derived from m-phenylenediamine with chain lengths of up to seven urea linkages were made by iterative synthetic pathways. Three families were synthesized: 4 and 20, bearing a terminal chiral sulfinyl group; 24, bearing a terminal rotatio
- Clayden, Jonathan,Lemiegre, Loic,Morris, Gareth A.,Pickworth, Mark,Snape, Timothy J.,Jones, Lyn H.
-
supporting information; experimental part
p. 15193 - 15202
(2009/03/12)
-
- 2,6-Dimethyl-4-nitrobenzoic anhydride (DMNBA): An effective coupling reagent for the synthesis of carboxylic esters and lactones
-
Various carboxylic esters are obtained at room temperature in excellent yields with high chemoselectivities from nearly equimolar amounts of carboxylic acids and alcohols using 2,6-dimethyl-4-nitrobenzoic anhydride with triethylamine by the promotion of 4-(dimethylamino)pyridine. The efficiency of the esterification is compared to those of other dehydrations using substituted benzoic anhydrides as coupling reagents. This method was successfully applied to the synthesis of threo-aleuritic acid lactone and the desired 17-membered ring compound was prepared in high yield at room temperature from the corresponding free trihydroxycarboxylic acid using 2,6-dimethyl-4-nitrobenzoic anhydride in the presence of 4-(dimethylamino)pyridine.
- Shiina, Isamu,Miyao, Ryo
-
experimental part
p. 1313 - 1328
(2009/07/05)
-
- Sequence-specific unusual (1→2)-type helical turns in α/β-hybrid peptides
-
This article describes novel conformationally ordered α/β-hybrid peptides consisting of repeating L-proline-anthranilic acid building blocks. These oligomers adopt a compact, right-handed helical architecture determined by the intrinsic conformational pre
- Prabhakaran, Panchami,Kale, Sangram S.,Sanjayan, Gangadhar J.,Puranik, Vedavati G.,Rajamohanan, P. R.,Chetina, Olga,Howard, Judith A. K.,Hofmann, Hans-Joerg
-
supporting information; experimental part
p. 17743 - 17754
(2009/08/07)
-
- Isotope effects in photochemistry: Application to chromatic orthogonality
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Equation Presented The main challenge in developing new wavelength-specific photolabile protecting groups is the rigorous control of the photolysis rate. This rate is controlled by two factors: the chromophore absorbance and the reaction quantum yield. Fine-tuning the properties by changing substituents or structural features is difficult, because both factors are independently affected. By the use of the kinetic isotope effect, we could tune the quantum yield without altering the absorbance, and hence control the overall reaction rate. We exemplified this approach with chromatically orthogonally protected diesters.
- Blanc, Aurelien,Bochet, Christian G.
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p. 2649 - 2651
(2008/02/08)
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- Synthesis of a novel C2-aryl pyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione library: Effect of C2-aryl substitution on cytotoxicity and non-covalent DNA binding
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A 23-member C2-aryl pyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione (PBD dilactam) library has been synthesized using Suzuki coupling, and the effect of base upon racemisation at the C11a-position during the cross-coupling reaction studied. Three library members (21, 30 and 33) were sufficiently cytotoxic in the NCI's preliminary screen to warrant further evaluation, and one (30, R = p-Br) was found to be cytotoxic at the sub-micromolar level in the A498 renal cancer cell line. DNA thermal denaturation studies suggested that this activity may be associated with non-covalent DNA interaction, and also demonstrated that introductin of C2-C3 unsaturation and addition of C2-aryl functionalities to the PBD dilactam skeleton significantly enhanced helix stabilisation compared to the unsubstituted PBD dilactam (6).
- Antonow, Dyeison,Jenkins, Terence C.,Howard, Philip W.,Thurston, David E.
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p. 3041 - 3053
(2008/02/01)
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- Preparation of novel antibacterial agents. Replacement of the central aromatic ring with heterocycles
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Discovery of novel antibacterial agents is a significant challenge. We have recently reported on our discovery of novel antibacterial agents in which we have rapidly optimized potency utilizing a parallel chemistry approach. These advanced leads suffer from high affinity for human serum albumin (HSA). In an effort to decrease the affinity for HSA we have prepared a series of heterocyclic analogs, which retained antibacterial activity and demonstrated reduced affinity for HSA.
- Li, Jianke,Wakefield, Brian D.,Ruble, J. Craig,Stiff, Cory M.,Romero, Donna L.,Marotti, Keith R.,Sweeney, Michael T.,Zurenko, Gary E.,Rohrer, Douglas C.,Thorarensen, Atli
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p. 2347 - 2350
(2008/12/21)
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- Auto-redox reaction: Tin(II) chloride-mediated one-step reductive cyclization leading to the synthesis of novel biheterocyclic 5,6-dihydro-quinazolino[4,3-b]quinazolin-8-ones with three-point diversity
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A tin (II) chloride-mediated short, efficient, and practical regioselective synthesis of biheterocyclic 5,6-dihydro-quinazolino[4,3-b]quinazolin-8-ones with three-point diversity is reported. A one-step reductive transformation of 2-(2-nitro-phenyl)-3H-quinazolin-4-one in various alcohols furnished the desired tetracyclic product in good yields with high purity.
- Roy, Abhijeet Deb,Subramanian, Arunachalam,Roy, Raja
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p. 382 - 385
(2007/10/03)
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- A one-pot synthesis of novel sugar derived 5,6-dihydro-quinazolino[4,3-b]quinazolin-8-ones: an entry towards highly functionalized sugar-heterocyclic hybrids
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An efficient and practical one-pot method for the synthesis of novel diversified sugar derived dihydro-quinazolino[4,3-b]quinazolin-8-ones has been reported. Various protected sugar hemiacetals were used to synthesize the hybrid tetracyclic ring system. The one-step reductive transformation of 2-(2-nitrophenyl)-3H-quinazolin-4-one with different sugar hemiacetals furnished the desired tetracyclic product in good yields and with high purity.
- Roy, Abhijeet Deb,Subramanian, Arunachalam,Mukhopadhyay, Balaram,Roy, Raja
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p. 6857 - 6860
(2007/10/03)
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- Studies on enantioselective allylic oxidation of olefins using peresters catalyzed by Cu(I)-complexes of chiral pybox ligands
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Enantioselective allylic oxidation of olefins with various peresters, using a catalytic amount of Cu(i)-pybox complex, can be tuned to achieve high asymmetric induction (up to 98% ee) by choosing a unique combination of a ligand and a perester at room temperature. The asymmetric induction in the reaction strongly depends on the nature of the substituents attached to the aryl ring of peresters. The presence of a gem-diphenyl group at C-5 and secondary or tertiary alkyl substituents at the chiral center (C-4) of the oxazoline rings is crucial for high enantioselectivity. A π-π stacking model has been proposed and discussed to explain the stereochemical outcome of the reaction. The Royal Society of Chemistry 2006.
- Ginotra, Sandeep K.,Singh, Vinod K.
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p. 4370 - 4374
(2008/09/19)
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- Novel heterocyclic trans olefin analogues of N-{4-[4-(2,3-dichlorophenyl) piperazin-1-yl]butyl}arylcarboxamides as selective probes with high affinity for the dopamine D3 receptor
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Dopamine D3 receptor subtypes have been hypothesized to play a pivotal role in modulating the reinforcing and drug-seeking effects induced by cocaine. However, definitive pharmacological investigations have been hampered by the lack of highly D3 receptor selective compounds that can be used in vivo. To address this problem, the potent and D3-receptor-selective antagonist NGB 2904 (1, 9H-fluorene-2-carboxylic acid {4-[(2,3-dichlorophenyl)-piperazin-1-yl]- butyl}-amide, Ki (hD3) = 2.0 nM, Ki (hD2L) = 112 nM, D2/D3 selectivity ratio of 56) was chosen as a lead structure for chemical modification in an attempt to reduce its high lipophilicity (c log D = 6.94) while optimizing D3 receptor binding affinity and D2/D3 selectivity. A series of >30 novel analogues were synthesized, and their binding affinities were evaluated in competition binding assays in HEK 293 cells transfected with either D2L, D3, or D4 human dopamine receptors using the high affinity, selective D2-like receptor antagonist 125I-IABN. Structural diversity in the aryl amide end of the molecule was found to have a major influence on (sub)nanomolar D3 receptor affinity and D2/D3 selectivity, which was optimized using a more rigid trans-butenyl linker between the aryl amide and the piperazine. Several analogues demonstrated superior D3 receptor binding affinities and selectivities as compared to the parent ligand. Compound 29 (N-{4-[4-(2,3-dichlorophenyl)-piperazin-1-yl]-trans-but-2-enyl} -4-pyridine-2-yl-benzamide) displayed the most promising pharmacological profile (Ki (hD3) = 0.7 nM, Ki (hD2L) = 93.3 nM, D2/D3 selectivity ratio of 133). In addition, this ligand inhibited quinpirole stimulation of mitogenesis at human dopamine D3 receptors transfected into Chinese hamster ovary (CHO) cells, with an EC50 value of 3.0 nM. Compound 29 was a nearly 5 times more potent antagonist at the D3 receptor than 1 (EC50 = 14.4 nM). Moreover, a decrease in c log D value of ~2 orders of magnitude was determined for this novel D3-receptor-preferring ligand, compared to 1. In summary, chemical modification of 1 has resulted in compounds with high affinity and selectivity for D3 receptors. The most promising candidate, compound 29, is currently being evaluated in animal models of cocaine abuse and will provide an important tool with which to elucidate the role of D3 receptors in drug reinforcement in vivo.
- Grundt, Peter,Carlson, Erin E.,Cao, Jianjing,Bennett, Christina J.,McElveen, Elizabeth,Taylor, Michelle,Luedtke, Robert R.,Newman, Amy Hauck
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p. 839 - 848
(2007/10/03)
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- A facile approach for new dibenzo [b,f][1,5] diazocinones
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The synthesis of new eight-membered cycle dibenzo[b,f][1,5]-diazocine-6- (5W)-one derivatives 11, 12 was developed. The key step in this synthesis was the intramolecular cyclization of the amino aldehyde precursors 9, 10 obtained by a selective reduction
- Pessoa-Mahana, Hernan,Martinez Aranguiz, Karen G.,Araya-Maturana, Ramiro,Pessoa-Mahana, C. David
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p. 1493 - 1500
(2007/10/03)
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