- Visible Light-Promoted Magnesium, Iron, and Nickel Catalysis Enabling C(sp3)-H Lactonization of 2-Alkylbenzoic Acids
-
A mild and practical C(sp3)-H lactonization protocol has been achieved by merging photocatalysis and magnesium (iron, nickel) catalysis. A diverse range of 2-alkylbenzoic acids with a variety of substitution patterns could be transformed into the corresponding phthalide products. Based on the mechanistic experimentation and reported prior studies, a possible mechanism for the benzylic oxidative lactonization reaction was proposed with the hypothetic photoactive ternary complex formed between the 2-alkylbenzoic acid substrate, magnesium ion, and bromate anion.
- Li, Sasa,Su, Mincong,Sun, Jie,Hu, Kunjun,Jin, Jian
-
supporting information
p. 5842 - 5847
(2021/07/31)
-
- Squaramide-catalyzed asymmetric intramolecular oxa-michael reaction of α,β-unsaturated carbonyls containing benzyl alcohol: Construction of chiral 1-substituted phthalans
-
Organocatalytic enantioselective intramolecular oxa-Michael reactions of benzyl alcohol bearing α,β-unsaturated carbonyls as Michael acceptors are presented herein. Using cinchona squaramide-based organocatalyst, enones as well as α,βunsaturated esters containing benzyl alcohol provided their corresponding 1,3-dihydroisobenzofuranyl-1-methylene ketones and 1,3-dihydroisobenzofuranyl-1-methylene esters in excellent yields with high enantioselectivities. In addition, enantioenriched 1,3-dihydroisobenzofuranyl-1-methylene ketone could be obtained from the Wittig/oxa-Michael reaction cascade of 1,3-dihydro-2-benzofuran-1-ol.
- Son, Eun Chae,Kim, Seung Yeon,Kim, Sung-Gon
-
p. 6826 - 6839
(2021/05/29)
-
- Enantioselective synthesis of 3-aryl-phthalides through a nickel-catalyzed stereoconvergent cross-coupling reaction
-
A nickel-catalyzed asymmetric Suzuki-Miyaura cross-coupling of racemic 3-bromo-phthalides and arylboronic acids was realized for the synthesis of diverse chiral 3-aryl-phthalides in moderate to excellent reaction yields. The reaction proceeded in a stereoconvergent manner and high enantioselectivities were observed for most examined examples. A number of functional groups like aldehyde, ester and bromide were well tolerated. Heteroaromatic boronic acids were also competent coupling partners in this reaction.
- Feng, Chen-Guo,Xu, Si-Yu,Zhang, Rui,Zhang, Shu-Sheng
-
supporting information
p. 4492 - 4496
(2021/05/31)
-
- Organocatalytic enantioselective synthesis of phthalans via Wittig/oxa-Michael cascade reaction
-
An enantioselective synthetic method for 1-substituted phthalans has been developed. The organocatalytic reaction between 1,3-dihydro-2-benzofuran-1-ols and Wittig reagents using cinchona squaramide-based organocatalyst proceeded with sequential Wittig reaction followed by an enantioselective intramolecular oxa-Michael reaction, yielding enantioenriched phthalans with moderate to good enantioselectivities.
- Son, Eun Chae,No, Jaeeun,Kim, Sung-Gon
-
p. 1473 - 1480
(2021/09/25)
-
- Design, synthesis and biological evaluation of novel thiohydantoin derivatives as potent androgen receptor antagonists for the treatment of prostate cancer
-
Prostate cancer (PC) is the most common malignancy in men worldwide. Here, two series of novel thiohydantoin derivatives of enzalutamide as potent androgen receptor (AR) antagonists were designed and synthesized. Among them, compound 31c was identified as an AR antagonist which is 2.3–fold more potent than enzalutamide. Molecular docking studies were performed to explain the improved potency of 31c at AR. In cell proliferation assays, 31c exhibited similar anti-proliferative activities with enzalutamide against hormone sensitive LNCaP cells and AR-overexpressing LNCaP/AR cells. These data indicate that 31c can be a good lead compound for further structure optimization for the treatment of prostate cancer.
- Wang, Ao,Wang, Yawan,Meng, Xin,Yang, Yushe
-
-
- N-Heterocyclic Carbene Catalyzed Ester Synthesis from Organic Halides through Incorporation of Oxygen Atoms from Air
-
Oxygenation reactions with molecular oxygen (O2) as the oxygen source provides a green and straightforward strategy for the construction of O-containing compounds. Demonstrated here is a novel N-heterocyclic carbene (NHC) catalyzed oxidative transformation of simple and readily available organic halides into valuable esters through the incorporation of O-atoms from O2. Mechanistic studies prove that the deoxy Breslow intermediate generated in situ is oxidized to a Breslow intermediate for further transformation by this oxidative protocol. This method broadens the field of NHC catalysis and promotes oxygenation reactions with O2.
- Tan, Hui,Wang, Shen-An,Yan, Zixi,Liu, Jianzhong,Wei, Jialiang,Song, Song,Jiao, Ning
-
supporting information
p. 2140 - 2144
(2020/12/01)
-
- Chiral Bicyclic Imidazole-Catalyzed Acylative Dynamic Kinetic Resolution for the Synthesis of Chiral Phthalidyl Esters
-
Utilizing a chiral bicyclic imidazole organocatalyst and adopting a continuous injection process, an alternative route has been developed for the efficient synthesis of chiral phthalidyl ester prodrugs via dynamic kinetic resolution of 3-hydroxyphthalides through enantioselective acylation (up to 99 % ee). The computational studies suggest a general base catalytic mechanism differing from the widely accepted nucleophilic catalytic mechanism. The structure analysis of the key transition states shows that the CH-π interactions and not the previously considered cation/π-π interactions between the catalyst and substrate is the dominant factor giving rise to the observed stereocontrol.
- Zhou, Muxing,Gridneva, Tatiana,Zhang, Zhenfeng,He, Ende,Liu, Yangang,Zhang, Wanbin
-
supporting information
p. 1641 - 1645
(2020/11/30)
-
- Synthesis of 3-Unsubstituted Phthalides from Aryl Amides and Paraformaldehyde via Ruthenium(II)-Catalyzed C–H Activation
-
A straightforward and convenient route has been developed for the synthesis of 3-unsubstituted phthalide derivatives from aryl amides and paraformaldehyde by ruthenium(II)-catalyzed C–H activation. The reaction proceeds through tandem ortho-hydroxymethylation of aryl amide and subsequent intramolecular lactonization.
- Zhou, Chao,Zhao, Junqi,Chen, Wenkun,Imerhasan, Mukhtar,Wang, Jun
-
supporting information
p. 6485 - 6488
(2020/10/02)
-
- A g-C3N4-based heterogeneous photocatalyst for visible light mediated aerobic benzylic C-H oxygenations
-
A metal-free heterogeneous photocatalytic system has been developed for highly efficient benzylic C-H oxygenations using oxygen as an oxidant. This visible light mediated oxidation reaction utilizes graphitic carbon nitride (g-C3N4) as a recyclable, nontoxic and low cost photocatalyst. Mild reaction conditions allow for the generation of synthetically and biologically valued isochromannones, phthalides, isoquinolinones, isoindolinones and xanthones from readily accessible alkyl aromatic precursors in good yields. The heterogeneous nature of the g-C3N4 catalytic system enables easy recovery and recycling as well as the use in multiple runs without loss of activity. The synthetic utility of this "green" methodology was further demonstrated by applying in bioactive and drug valued target syntheses.
- Geng, Pengxin,Tang, Yurong,Pan, Guanglong,Wang, Wentao,Hu, Jinchuan,Cai, Yunfei
-
supporting information
p. 6116 - 6122
(2019/11/20)
-
- Platinum-on-Carbon-Catalyzed Aqueous Oxidative Lactonization of Diols by Using Molecular Oxygen
-
A lactonization of various diols catalyzed by platinum on carbon (Pt/C) in water under an atmosphere of molecular oxygen was developed. Derivatives of 1,4- 1,5- and 1,6-diols were transformed into the corresponding five-, six-, and seven-membered lactones by the present oxidative lactonization method.
- Ban, Kazuho,Sajiki, Hironao,Sawama, Yoshinari,Takakura, Ryoya
-
p. 1919 - 1923
(2019/09/30)
-
- Method for synthesizing roxadustat intermediate
-
The invention belongs to the technical field of chemical preparation, and discloses a method for synthesizing a roxadustat intermediate. The method comprises the following steps: mixing 4-bromo-2-methylbenzoic acid and a solvent to obtain a mixture 1, adding N-bromosuccinimide and an initiator into the mixture 1, performing uniform mixing to obtain a mixture 2, and performing a reaction to obtainthe roxadustat intermediate 5-bromophthalide. The method provided by the invention has the following advantages: the method for synthesizing the roxadustat intermediate provided by the invention adopts the 4-bromo-2-methylbenzoic acid as the reaction raw material, the raw material is simple and easy to obtain, the costs are low, the reaction is easy to control, and the final product 5-bromophthalide has a yield of 96.5% or more and purity of 98.5% or more.
- -
-
Paragraph 0023-0059
(2019/12/08)
-
- Discovery and development of novel salicylate synthase (MbtI) furanic inhibitors as antitubercular agents
-
We report on the virtual screening, synthesis, and biological evaluation of new furan derivatives targeting Mycobacterium tuberculosis salicylate synthase (MbtI). A receptor-based virtual screening procedure was applied to screen the Enamine database, identifying two compounds, I and III, endowed with a good enzyme inhibitory activity. Considering the most active compound I as starting point for the development of novel MbtI inhibitors, we obtained new derivatives based on the furan scaffold. Among the SAR performed on this class, compound 1a emerged as the most potent MbtI inhibitor reported to date (Ki = 5.3 μM). Moreover, compound 1a showed a promising antimycobacterial activity (MIC99 = 156 μM), which is conceivably related to mycobactin biosynthesis inhibition.
- Chiarelli, Laurent R.,Mori, Matteo,Barlocco, Daniela,Beretta, Giangiacomo,Gelain, Arianna,Pini, Elena,Porcino, Marianna,Mori, Giorgia,Stelitano, Giovanni,Costantino, Luca,Lapillo, Margherita,Bonanni, Davide,Poli, Giulio,Tuccinardi, Tiziano,Villa, Stefania,Meneghetti, Fiorella
-
supporting information
p. 754 - 763
(2018/06/26)
-
- Preparation method of novel isobenzofuranone intermediate
-
The invention discloses a synthetic method of an important intermediate of novel diuretic drug ROMK inhibitor. The synthetic method comprises the following steps: adopting 4-nitro phthalimide as the starting material, performing two-step reaction, diazotization reaction, Suzuki reaction and epoxidation reaction, thus obtaining the important intermediate 5-epoxy ethyl isobenzofuranone of the ROMK inhibitor. The preparation method provided by the invention is mild in route reaction conditions, simple in after-treatment, high in yield, and capable of avoiding the use of toxic gases and bioenzymecatalysts.
- -
-
Paragraph 0013
(2018/09/08)
-
- Palladium (II)-Catalyzed Decarboxylative Cross-Dehydrogenative Coupling: Direct Synthesis of meta-Substituted Biaryls from Aromatic Acids
-
A palladium-catalyzed tandem process of simple aromatic acids has been achieved to afford meta-substituted biaryls in moderate to good yields. The reaction proceeds via carboxyl-directed intermolecular cross-dehydrogenative coupling and subsequent decarboxylation. The new C?C bonds in this transformation are formed in the ortho position of carboxyl and the reaction tolerates electron-rich acids. Both symmetrical and unsymmetrical meta-substituted biaryls can be directly synthesized via this method. (Figure presented.).
- Pu, Fan,Zhang, Lin-Yan,Liu, Zhong-Wen,Shi, Xian-Ying
-
supporting information
p. 2644 - 2649
(2018/07/29)
-
- Industrial preparation method of 5-bromophthalide
-
The invention relates to a preparation method of 5-bromophthalide and mainly solves such production technical problems of an existing preparation method as expensive raw material, dangerous and complex operation, relatively low yield, high quantity of generated three wastes and etc. The technical scheme of the invention is as follows: an industrial preparation method of 5-bromophthalide is characterized in that 5-bromophthalide is obtained through three step reactions of bromination, ammoniation and reduction by taking a conventional and easily available ammoniation as a raw material. The chemical reaction formula is as shown in the description. The method provided by the invention is mainly used for industrial preparation of 5-bromophthalide.
- -
-
Paragraph 0019; 0020; 0021; 0022
(2017/09/01)
-
- 6 - [...] indoline - 1 - one synthetic method
-
The invention provides a synthesis method of 6-bromoisoindolinyl-1-one, which comprises the following steps: (a) carrying out substitution reaction on a compound (I) and a bromination reagent in an organic solvent to obtain a compound (IIa)-compound (IIb) mixture; (b) carrying out hydrolysis reaction on the compound (IIa)-compound (IIb) mixture under alkaline conditions, and separating a compound (IIIa) out of the obtained product; (c) carrying out cyclization reaction on the compound (IIIa) in an acidic solution to obtain the compound (IIa); (d) reacting the compound (IIa) and thionyl chloride in an organic solvent under the action of a catalyst to obtain a compound (IV); and (e) carrying out reflux reaction on the compound (IV) in ethanol, and adding ammonia water to react, thereby obtaining the compound (V) 6-bromoisoindolinyl-1-one. The method has the advantages of simple route, controllable conditions and high yield, and can easily implement industrial production. The reaction route of the method is disclosed in the specification.
- -
-
Paragraph 0045-0050
(2018/01/13)
-
- A simple, convenient, highly regioselective synthesis of isobenzofuran-1(3H)-ones (phthalides) as well as Maculalactone A & B, the Bioactive Butyrolactones
-
Bacground: Among the class of oxygen heterocycles, the benzoannulated lactone (3H-isobenzofuran-1-one or phthalide) moiety is found in many natural products. Phthalides possess a wide range of biological activity e.g. (-)-Hidrastine is active at the human opioid receptor known as CCR5, while fuscinarin interferes with HIV entry into cells. Phthalides also represent an important structural subunit in numerous natural products that exhibit a wide range of biological activities, such as antispasmodic, antifungal, vasodilators, and coronary artery dilators. Except their biological activities, phthalides are also versatile starting material for the synthesis of various important organic compounds, including the key intermediates in the synthesis of functionalized naphthalenes and anthracenes, which in turn are used as synthons for tricyclic and tetra cyclic aromatic natural products. The present communication describes a simple but efficient and expedient one pot strategy for the synthesis of phthalides. Methods: Diethyl phthalate was considered initially for the cyclization strategy using different metal hydrides at variable temperatures. The reaction was carried out at-30°C with 2.5 equivalent of DIBAL-H, the phthalide was obtained in ~68% yield along with minor amount of alcohol (~10%) and the unreacted starting material (~12%). In the reaction protocol, other solvents such as tetrahydrofuran, diethyl ether, and chlorobenzene were found to be effective in cyclization at-30°C. But yield of the phthalide was observed to be less compare to CH2Cl2. Further decrease of the reaction temperature up to-78°C showed no effect on the yield of cyclized product. Use of 3 equivalent of DIBAL-H dramatically decreases the yield of the cyclized product (30%) and increased the amount of reduced product (60%). Results: The promising outcome of the above observations encouraged us to study the general scope and limitations of this protocol for the reduction of different substituted phthalides. It was found that diethyl esters of nitro-, bromo-, 4'-methyl-biphenyl-, 3'-methyl-biphenyl-, 2'-methyl-biphenyl-, biphenyl-, 4-pyrazin-2-yl-, and 4-(4-methyl-Thiazol-5-yl)-substituted phthalic acids readily underwent reduction with DIBAL-H to afford the corresponding phthalides in moderate to good yields. Conclusion: We developed a simple, convenient, one step protocol for the synthesis of isobenzofuran-1(3H)-ones (phthalides) from phthalate esters in moderate to good yields. We have also demonstrated a short and effective route to prepare two bioactive butyrolactones, viz., maculalactone A & B. In our opinion, the present approach is general in nature and could be useful to design diverse butyrolactone skeletons.
- Joardar, Soumen,Chakravorty, Santanu,Das, Sakti P.
-
p. 127 - 134
(2016/03/01)
-
- A PROCESS FOR THE SYNTHESIS OF CARBOXYLIC ACID DERIVATIVES
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The present invention discloses one-pot synthesis of various carboxylic acid derivatives using copper catalyst and sodium cyanide as the cyanide source for bringing in carbonylative coupling in a single step.
- -
-
Page/Page column 8-9; 15
(2015/05/19)
-
- Dehydrogenative α-oxygenation of ethers with an iron catalyst
-
Selective α-oxidation of ethers under aerobic conditions is a long-pursued transformation; however, a green and efficient catalytic version of this reaction remains challenging. Herein, we report a new family of iron catalysts capable of promoting chemoselective α-oxidation of a range of ethers with excellent mass balance and high turnover numbers under 1 atm of O2 with no need for any additives. Unlike metalloenzymes and related biomimetics, the catalyst produces H2 as the only byproduct. Mechanistic investigations provide evidence for an unexpected two-step reaction pathway, which involves dehydrogenative incorporation of O2 into the ether to give a peroxobisether intermediate followed by cleavage of the peroxy bond to form two ester molecules, releasing stoichiometric H2 gas in each step. The operational simplicity and environmental friendliness of this methodology affords a useful alternative for performing oxidation, while the unique ability of the catalyst in oxygenating a substrate via dehydrogenation points to a new direction for understanding metalloenzymes and designing new biomimetic catalysts.
- Gonzalez-De-Castro, Angela,Robertson, Craig M.,Xiao, Jianliang
-
supporting information
p. 8350 - 8360
(2014/06/24)
-
- Dehydrogenative lactonization of diols in aqueous media catalyzed by a water-soluble iridium complex bearing a functional bipyridine ligand
-
A new catalytic system for the dehydrogenative lactonization of a variety of benzylic and aliphatic diols in aqueous media was developed. By using a water-soluble, dicationic iridium catalyst bearing 6,6′-dihydroxy-2, 2′-bipyridine as a functional ligand, highly atom economical and environmentally benign synthesis of various lactones was achieved in good to excellent yields. Recovery and reuse of the catalyst were also accomplished by a simple phase separation and the recovered catalyst maintained its high activity at least until the fifth run. Copyright
- Fujita, Ken-Ichi,Ito, Wataru,Yamaguchi, Ryohei
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p. 109 - 112
(2014/01/23)
-
- Facile organocatalytic domino oxidation of diols to lactones by in situ-generated TetMe-IBX
-
The domino oxidation of diols to lactones is an important transformation, and catalytic protocols that allow this conversion smoothly are scarce. Capitalizing on the established reactivity of tetramethyl-IBX (TetMe-IBX) and its in situ generation in the presence of a co-oxidant, such as oxone, we have shown that a variety of diols can be converted to the corresponding lactones in respectable yields by employing the precursor of TetMe-IBX, namely, tetramethyl-o-iodobenzoic acid (TetMe-IA), as a catalyst in 5 mol % in the presence of 2 equiv of oxone.
- Jhulki, Samik,Seth, Saona,Mondal, Manas,Moorthy, Jarugu Narasimha
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p. 2286 - 2293
(2014/03/21)
-
- Catalytic and chemoselective oxidation of activated alcohols and direct conversion of diols to lactones with in situ-generated bis-IBX catalyst
-
The twisted 3,3′-diiodo-2,2′,6,6′-tetramethoxybiphenyl-4, 4′-dicarboxylic acid (DIDA) was designed and synthesized for the in situ generation of Bis-IBX and catalytic oxidations. The seemingly better solubility of the in situ-generated Bis-IBX and the attenuated reactivity arising from its unique structural features and methoxy substituents allowed the catalytic oxidation of activated alcohols selectively using DIDA/oxone. Chemoselective oxidations were demonstrated for substrates containing two different hydroxy groups. Furthermore, the unique reactivity of DIDA was demonstrated for sequential oxidation reactions of 1,4- and 1,6-diols to give lactones catalytically in respectable yields.
- Seth, Saona,Jhulki, Samik,Moorthy, Jarugu Narasimha
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p. 2445 - 2452
(2013/05/22)
-
- LIGHT-DRIVEN ROTARY MOLECULAR MOTORS
-
Compounds of Formula (1) are disclosed. Cb is a carbocyclic or heterocyclic group having an atom within the cyclic structure selected from C, N, Si, and Cr and singly bound to A. A is CR, COR, CSR, CNR2, CCN, CCONR2, CNO2, CNNAr, CX′, or N. Cr is a chromophore having a substantially planar cyclic structure. The compounds function as nanometer-scale rotary molecular motors powered and controlled by light energy. The design of the molecular motor devices is flexible so that the rotary direction, drive light wavelength, and other physical characteristics can be varied. The compounds can be chemically functionalized to allow it to be integrated into or attached to a variety of structures. The device can be used in applications where mechanical power, positional control, and information encoding are to be generated at the size scale of individual molecules.
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Page/Page column 15
(2011/04/19)
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- PENTACYCLINE COMPOUNDS
-
The present invention is directed to a compound represented by Structural Formula (I): or a pharmaceutically acceptable salt thereof. The variables for Structural Formula (I) are defined herein. Also described is a pharmaceutical composition comprising the compound of Structural Formula (I) and its therapeutic use.
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Page/Page column 170-171
(2010/12/17)
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- Synthesis and biological activity of n-butylphthalide derivatives
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A series of n-butylphthalide derivatives were designed and synthesized. The in vitro activities of these compounds were evaluated by a resting tension of isolated rat thoracic aorta ring assay. Compounds 4g and 4i were found to be more active than n-butylphthalide.
- Wang, Wei,Cha, Xue-Xiang,Reiner, John,Gao, Yuan,Qiao, Hai-Ling,Shen, Jia-Xiang,Chang, Jun-Biao
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experimental part
p. 1941 - 1946
(2010/06/19)
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- PIPERAZINYLPHENALKYL LACTAM/AMINE LIGANDS FOR THE 5HT1B RECEPTOR
-
The present invention relates to novel derivatives, that are compounds of Formula (I), wherein R1, R2, R3, R14, X, Y, n and m are defined herein, their pharmaceutically acceptable salts, pharmaceutical compositions and methods using said compounds in treating or preventing depression, anxiety, obsessive compulsive disorder (OCD) and other disorders for which selective antagonists, inverse agonists and partial agonists of serotonin 1 (5-HT1) receptors, specifically, antagonists of 5-HT1B are useful.
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Page/Page column 70
(2010/11/30)
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- Furan ring opening - Isocoumarine ring closure: A recyclization reaction of 2-carboxyaryldifurylmethanes
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A general method for the synthesis of isocoumarine derivatives has been developed. Bis(5-R-2-furyl)methylbenzoic acids (R = methyl, ethyl) underwent recyclization and subsequent cyclization into tetracyclic isochromene-1-one derivatives under treatment with hydrogen chloride in methanol. It has been shown that intermediate 4-(5-R-furan-2-yl)-3-(3-oxo-3-R-propyl)-isochromene-1- ones can be obtained selectively by varying a concentration of the hydrogen chloride and reaction times. In the case of R = tert-butyl only corresponding 4-[5-(tert-butyl)-2-furyl]-3-(4,4-dimethyl-3-oxopentyl)-1-isochromenones were isolated regardless of the reaction conditions.
- Abaev, Vladimir T.,Dmitriev, Artem S.,Gutnov, Andrey V.,Podelyakin, Sergey A.,Butin, Alexander V.
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p. 1195 - 1204
(2007/10/03)
-
- A short and efficient synthesis of isoindolin-1-ones
-
Here, we report a short and efficient synthesis of isoindolin-1-ones. Base-induced cyclization of o-hydroxymethyl-benzamides, which was easily prepared from the corresponding phthalides and amines, led predominantly to N-alkylation in good yield. The reaction proceeded under mild conditions and bromine and nitrile substituents were tolerated. The selectivity is explained by HASB theory. Georg Thieme Verlag Stuttgart.
- Tsuritani, Takayuki,Kii, Satoshi,Akao, Atsushi,Sato, Kimihiko,Nonoyama, Nobuaki,Mase, Toshiaki,Yasuda, Nobuyoshi
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p. 801 - 803
(2007/10/03)
-
- SELECTIVE ESTROGEN RECEPTOR MODULATORS
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The present invention relates to a selective estrogen receptor modulators of formula I (I); or a pharmaceutical acid addition salt thereof; and of formula II (II); or a pharmaceutical salt thereof; useful, e.g., for treating endometriosis and/or uterine leiomyoma/leiomyomata.
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Page/Page column 29-30
(2010/02/13)
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- Efficient synthesis of isobenzofuran-1(3H)-ones (Phthalides) and selected biological evaluations
-
The studies presented here deal with the convenient and efficient one-step conversion of o-alkylbenzoic acids into their corresponding isobenzofuran-1 (3H)-ones (phthalides) using NaBrO3/NaHSO3 in a two-phase system. A range of o-alkylbenzoic acids was used with the object of getting a variety of phthalide derivatives as multipurpose biologically active compounds. Seventeen phthalides have been synthesized and tested for cytotoxicity, antibacterial and antifungal activities. Some of these compounds showed promising cytotoxic effects against Artemia salina. Compounds 4j-4p were highly active against Gram-negative and Gram-positive bacteria among all tested compounds. In the fungicidal assay, the compounds showed a broad spectrum of activity against six fungi. All compounds were characterized via elemental analysis, UV, IR, mass and-NMR spectroscopy. ECV · Editio Cantor Verlag.
- Bayer, Ernst,Hayat, Safdar,Atta-Ur-Rahman,Choudhary, M. Iqbal,Khan, Khalid Mohammed,Shah, Syed Tasadaque Ali,Imran-Ul-Haq,Anwar, M. Usman,Voelter, Wolfgang
-
p. 588 - 597
(2007/10/03)
-
- (3Z)-3-(2,3-dihydro-1H-inden-1-ylidene)-1,3-dihydro-2H-indol-2-ones as kinase inhibitors
-
The present invention relates to organic molecules capable of modulating tyrosine kinase signal transduction in order to regulate, modulate and/or inhibit abnormal cell proliferation.
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-
-
- PROCESS FOR THE PREPARATION OF 5-BROMOPHTHALIDE
-
A process, which comprises reducing 4-bromophthalic anhydride in an organic solvent, to obtain a mixture of 5-bromophthalide and 6-bromophthalide, acidifying the reaction mixture, separating the same into aqueous and organic phases, and selectively crystallizing 5-bromophthalide from the organic phase.
- -
-
Page 7; 16-17
(2008/06/13)
-
- An alternative method for the synthesis of γ-lactones by using cesium fluoride-celite/acetonitrile combination
-
A variety of 2-(1-bromoalkyl) benzoic acids 4 undergo intramolecular nucleophilic substitution reaction when treated with a CsF-Celite as solid base in acetonitrile under reflux condition to give the corresponding cyclized phthalides in moderate to very good yield. These 2-(1-bromoalkyl) benzoic acids 4 are formed by the α-bromination of 2-alkylbenzoic acids 3 using N-bromosuccinimide and a catalytic amount of α,α′ -azoisobutyronitrile in carbon tetrachloride under reflux.
- Khan, Khalid Mohammed,Hayat, Safdar,Zia-Ullah,Atta-ur-Rahman,Iqbal-Choudhary,Maharvi, Ghulam Murtaza,Bayert, Ernst
-
p. 3435 - 3453
(2007/10/03)
-
- An improved method for the synthesis of γ-lactones using sodium bromate and sodium hydrogen sulfite
-
o-Alkylbenzenecarboxylic acids are treated with a sodium bromate and sodium hydrogen sulfite reagent under a two-phase system using ethyl acetate as solvent, under mild conditions to give the corresponding cyclized phthalides in moderate to satisfactory yield. Intermediately the α-brominated alkylbenzenecarboxylic acids are formed by the in situ generated hypobromous acid. These α-brominated acids undergo an intramolecular nucleophilic substitution reaction to afford the corresponding γ-lactones.
- Hayat, Safdar,Atta-ur-Rahman,Choudhary, M. Iqbal,Khan, Khalid Mohammed,Bayer, Ernst
-
p. 1647 - 1649
(2007/10/03)
-
- Anti-inflammatory phthalazinones
-
A compound useful as anti-inflammatory agents in warm-blooded animals of the formula STR1 wherein X is a member of the class of ethylene and ethenyl and is substituted for hydrogen in the sixth or seventh position of the 1(2H)-phthalazinone ring Y is a member of the class of hydrogen and hydroxyl R1 is a member of the class of hydrogen, alkyl, alkoxy, hydroxyl, halogen, nitro, --NR3 R4, --COR5 and --O--A wherein A is a mineral acid residue which with --O-- forms an ester or the alkali metal salt of said ester, R2 is a member of the class of hydrogen, alkyl, phenyl, substituted phenyl, heteroaryl, hydroxyalkylene, polyhydroxyalkylene, aminoalkylene, alkylaminoalkylene, and carboxyalkylene, R3, R4 are independently from the class of hydrogen, alkyl, aminoalkylene or alkylaminoalkylene, R5 is a member of the class of OR3 and STR2 for example hydroxyl, methoxyl, 2-dimethylaminoethoxyl or 2-dimethylaminoethylamino, and wherein by alkyl and alkylene is meant respectively a mono- or divalent saturated aliphatic radical containing up to about eight carbon atoms, wherein the nitrogen of the alkylamino or alkylaminoalkylene may form a heterocycle with the alkyl or alkylene groups, wherein substituted phenyl may be substituted by, for example, alkyl, hydroxyl, alkoxy, halogen, nitro or amino, wherein heteroaryl may be, for example, 2-pyridyl.
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