cas 641-70-3, 3-Nitrophthalic anhydride | Articles data

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Solvent-free synthesis of new chalcone derivatives from 3-nitro phthalic acid and evaluation of their biological activities
Synthesis of 2-(4-Acetyl-phenyl)-4-nitro-isoindole-1, 3-dione chalcones were performed by fusion of 3-nitro phthalic anhydride with p-aminoacetophenone. Then the later was grinded with different aromatic aldehydes in the presence of sodium hydroxide to produce new chalcones derivatives A3-10 without using any solvent formation of new Narylphthailimide chalcones were confirmed by FT-IR,1HNMR, 13CNMR spectroscopy and all final compounds were tested for their antifungal and antibacterial activity some of them showed more biological activity than the standard drugs.
Ahamed, Luma S.,Ali, Rana Abid,Ahmed, Rana S.
p. 2963 - 2968
(2021/05/28)

ANTIVIRAL 1,3-DI-OXO-INDENE COMPOUNDS
This disclosure provides compounds of Formula (I) as described herein, along with pharmaceutically acceptable salts, pharmaceutical compositions containing such compounds, and methods to use these compounds, salts and compositions for treating viral infections.
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Paragraph 0239-0240

(2021/10/22)

ANTIVIRAL 1,3-DI-OXO-INDENE COMPOUNDS
The invention provides compounds of Formula (I): as described herein, along with pharmaceutically acceptable salts, pharmaceutical compositions containing such compounds, and methods to use these compounds, salts and compositions for treating viral infections.
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Paragraph 0264

(2021/10/22)

Synthesis process for continuously preparing pomalidomide by using microchannel reactors
The invention discloses a synthesis process for continuously preparing pomalidomide by using microchannel reactors. The synthesis process comprises the following steps tha (1) 3-nitrophthalic acid isdissolved in acetic anhydride, and a reaction is performed to obtain 3-nitrophthalic anhydride; (2) 3-nitrophthalic anhydride is dissolved in formic acid to prepare a homogeneous solution A; (3) 3-aminopiperidine-2,6-dione is dissolved in ammonium formate and formic acid to prepare a homogeneous solution B; (4) palladium on carbon and methanol are prepared into suspension C; (5) the homogeneous solution A and the homogeneous solution B are simultaneously pumped into a microstructured mixer I in a microchannel reaction device separately, and after mixing, the mixture is introduced into a microstructured reactor I; (6) the suspension C and an effluent from the microstructured reactor I are simultaneously pumped into a microstructured mixer II in the microchannel reaction device separately while the step (5) is carried out, and after mixing, the mixture is introduced into a microstructured reactor II; and (7) an effluent from the microstructured reactor II is collected to obtain pomalidomide.
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Paragraph 0052-0054

(2020/03/06)

Preparation method of 3-nitrophthalic anhydride
The invention relates to a preparation method of 3-nitrophthalic anhydride. The method includes the following steps: placing 3-nitrophthalic acid in a reaction solvent, adding a catalyst, and heatingfor reaction; and removing the reaction solvent and the catalyst from an obtained substance under negative pressure to obtain the 3-nitrophthalic anhydride. In the preparation method, the 3-nitrophthalic acid raw material can be easily obtained, the 3-nitrophthalic anhydride is synthesized by direct catalytic dehydration in one step, and the preparation method has the advantages of simple process,low cost, high yield and no by-products.
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Paragraph 0013-0015

(2019/04/10)

Synthesis and chemiluminescent properties of amino-acylated luminol derivatives bearing phosphonium cations
The monitoring of reactive oxygen species in living cells provides valuable information on cell function and performance. Lately, the development of chemiluminescence-based reactive oxygen species monitoring has gained increased attention due to the advantages posed by chemiluminescence, including its rapid measurement and high sensitivity. In this respect, specific organelle-targeting trackers with strong chemiluminescence performance are of high importance. We herein report the synthesis and chemiluminescence properties of eight novel phosphonium-functionalized amino-acylated luminol and isoluminol derivatives, designed as mitochondriotropic chemiluminescence reactive oxygen species trackers. Three different phosphonium cationic moieties were employed (phenyl, p-tolyl, and cyclohexyl), as well as two alkanoyl chains (hexanoyl and undecanoyl) as bridges/linkers. Synthesis is accomplished via the acylation of the corresponding phthalimides, as phthalhydrazide precursors, followed by hydrazinolysis. This method was chosen because the direct acylation of (iso)luminol was discouraging. The new derivatives’ chemiluminescence was evaluated and compared with that of the parent molecules. A relatively poor chemiluminescence performance was observed for all derivatives, with the isoluminol-based ones being the poorest. This result is mainly attributed to the low yield of the fluorescence species formation during the chemiluminescence oxidation reaction.
Pantelia, Anna,Daskalaki, Ira,Consuelo Cuquerella,Rotas, Georgios,Miranda, Miguel A.,Vougioukalakis, Georgios C.
(2019/11/11)

METHOD
The invention provides mitochondria-targeted chemiluminescent agents and their use in methods of photodynamic therapy (PDT). In particular, the invention provides compounds of general formula (I), and their pharmaceutically acceptable salts: (I) in which A represents a chemiluminescent moiety; each L, which may be the same or different, is either a direct bond or a linker; each B, which may be the same or different, represents a mitotropic moiety; n is an integer from 1 to 3, preferably 1; and x is an integer from 1 to 3, preferably 1. Such compounds find particular use in the treatment of deeply- sited tumours, e.g. glioblastoma multiforme (GBM), when used in combination with a photosensitizer or photosensitizer precursor.
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Page/Page column 33

(2020/01/11)

Preparation method of 3-nitrophthalic anhydride
Belonging to the field of fine chemical industry, the invention discloses a preparation method of 3-nitrophthalic anhydride. The method provided by the invention adopts 3-nitrophthalic acid as the starting raw material, carries out Vilsmeier reaction with acyl chloride under the action of a catalyst to obtain 3-nitrophthalic anhydride. The invention screens different acyl chlorides, different solvents and different amide reaction conditions, at the same time avoids use of dangerous and national precursor controlled chemicals in the compound preparation process, and makes the preparation process unrestricted. In the preparation process, the organic solvent can be recycled, the production cost is reduced, at the same time the post-treatment is economical and simple, and the product has highyield and purity.
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Paragraph 0021; 0023; 0024; 0026; 0028; 0030; 0033

(2018/11/22)

Discovery of Wogonin-based PROTACs against CDK9 and capable of achieving antitumor activity
Wogonin is a natural product isolated from the Scutellaria baicalensis and has been proved to be a potent and selective inhibitor of CDK9. Using this scaffold, we designed and synthesized a series of proteolysis targeting chimeras (PROTACs) targeting CDK9 by recruiting ubiquitin E3 ligase cereblon (CRBN). For constructing diverse Wogonin-based PROTACs, a “click chemistry” approach was employed for the synthesis of CDK9-targeting PROTACs. The results of western blotting assays showed that compounds containing triazole group in the linker could selectively downregulate the intracellular CDK9 level. Among these compounds, 11c could selectively degrade CDK9 in a concentration-dependent manner. In addition, the application of the proteasome inhibitor MG132 and CRBN siRNA silencing confirmed that 11c could promote the proteasome-dependent and CRBN-dependent degradation. Consistent with the degradation of the CDK9 protein, 11c selectively inhibits proliferation of CDK9-overexpressed cancer cells. Thus, our Wogonin-based PROTAC would be an efficient probe that induces the degradation of CDK9.
Bian, Jinlei,Ren, Jie,Li, Yongren,Wang, Jubo,Xu, Xi,Feng, Yifan,Tang, Hui,Wang, Yajing,Li, Zhiyu
supporting information
p. 373 - 381
(2018/10/08)

A 3 - phthalic acid synthetic method (by machine translation)
The invention discloses a 3 - phthalic acid synthetic method, the raw material 3 - nitrophthalic acid is dissolved by acetyl chloride solvent dehydration is carried out, after the dehydration by the fluorination potassium [...], then adding thionyl chloride to remove the by-product generated in the process of fluoro, purification to obtain the target compound 3 - phthalic acid. The invention relates to 3 - nitrophthalic acid as the synthetic 3 - phthalic acid raw material, the raw material is cheap, simple process, high yield; by adjusting the PH of the method, the product from the sulfolane solvent in very good separation out, solves the high boiling point of the solvent is not easily evaporated difficult; using acetyl chloride as dehydration solvent, not only replacing the drug control acetic anhydride, but also reduces the acetic anhydride in the dehydration process of the acetic acid by-product, mild reaction conditions after processing is simple and convenient. (by machine translation)
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Paragraph 0015; 0021; 0022

(2018/10/19)

AZA-PHENALENE-3-KETONE DERIVATIVE, PREPARATION METHOD THEREOF, AND ITS APPLICATION AS PARP INHIBITOR
Disclosed are an aza-phenalene-3-ketone derivative, a preparation method thereof and its application as a PARP inhibitor. The aza-phenalene-3-ketone derivative has the following structure: wherein R is hydrogen, methyl, ethyl, isopropyl, benzyl or 3-methyl-3-butenyl. The aza-phenalene-3-ketone derivative has very high activity for inhibiting PARP, thereby providing a good basis for new drug research of developing a nitrogen-doped phenalene-3-ketone compound as PARP inhibitor to treat cancer.
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Paragraph 0019

(2018/05/26)

Efficient cyclodehydration of dicarboxylic acids with oxalyl chloride
Literature examples illustrating the use of oxalyl chloride to prepare dicarboxylic acid anhydrides are surprisingly limited. At the same time, we have discovered a method involving the use of this readily available reagent which allowed the preparation of novel cyclic anhydrides where other, more conventional, methods had failed. Herein, we demonstrate that the method is applicable to a wide diversity of substrates, delivers good to excellent yields of cyclic anhydrides without chromatographic purification and can be considered a synthetic tool of choice whenever dicarboxylic acid cyclodehydration is required.
Kantin, Grigory,Chupakhin, Evgeny,Dar'in, Dmitry,Krasavin, Mikhail
supporting information
p. 3160 - 3163
(2017/07/18)

PROCESS FOR THE PREPARATION OF POMALIDOMIDE AND ITS PURIFICATION
The present invention is related to an improved process for the preparation of Pomalidomide with higher yields and high purity. Particularly the present invention relates to form A preparation of Pomalidomide and its purification. wherein the present process doesn't involve use of dioxane solvent and avoids higher temperatures.
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Page/Page column 5

(2018/04/11)

New synthesis route for the preparation of pomalidomide
A new route for the preparation of pomalidomide is described in the study. The synthetic procedure starts from 4-nitroisobenzofuran-1,3-dione and 3-aminopiperidine-2,6-dione hydrochloride via a three-step reaction resulting in a total yield of 65% with a high-performance liquid chromatographic (HPLC) purity of 99.56% and a low palladium residue level of 2?ppm. This method can be deemed as an efficient, practical, and environmentally friendly synthetic route for the preparation of pomalidomide.
Huang, Daowei,Shen, Chengwu,Wang, Wenya,Huang, Lei,Ni, Feng,Li, Jianqi
p. 1343 - 1348
(2016/09/03)

Preparation anchors Ma Duan one-pot synthesis (by machine translation)
The invention relates to a method for preparing pomalidomide (compound I) by a one-pot process. The method comprises the following steps: reacting a raw material 3-nitrophthalic acid disclosed as Formula (II) with acetic anhydride in an acidic solvent to prepare 3-nitrophthalic anhydride disclosed as Formula (III), carrying out condensation reaction with 3-aminopiperidyl-2,6-dione hydrochloride disclosed as Formula (IV) under the action of an alkali, and finally, reducing with iron powder, thereby preparing the pomalidomide (compound I) by the one-pot process. The method has the advantages of high efficiency, high yield, low cost, high safety and environmental protection.
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Paragraph 0035

(2017/03/08)

Synthesis and evaluation of in vitro and in vivo trypanocidal properties of a new imidazole-containing nitrophthalazine derivative
A series of new phthalazine derivatives (1-4) containing imidazole rings and functionalized with nitro groups in the benzene ring of the phthalazine moiety were prepared and identified on the basis of their MS, elemental analyses and bidimensional 1H and 13C NMR data, and their trypanocidal activity was tested. The 8-nitrosubstituted compound (3) was more active in vitro against Trypanosoma cruzi and less toxic against Vero cells than the reference drug benznidazole, and showed a SI value that was 47-fold better than the reference drug in amastigote forms. It also remarkably reduced the infectivity rate in Vero cells and decreased the reactivation of parasitemia in immunodeficient mice. Ultrastructural alterations found in epimastigotes treated with 3 confirmed extensive cytoplasm destruction in the parasites, whereas histopathological analysis of the hearts of mice infected and treated with 3 resulted in a decrease in cardiac damage. Biochemical markers showed that livers, hearts, and kidneys of treated mice were substantially unaffected by the administration of 3, despite the presence of the potentially toxic nitro group. It was also found that this compound selectively inhibited the antioxidant parasite enzyme Fe-superoxide dismutase (Fe-SOD) in comparison with human CuZn-SOD, and molecular modeling suggested interaction with the H-bonding system of the iron-based moiety as a feasible mechanism of action against the enzyme.
Olmo, Francisco,Gómez-Contreras, Fernando,Navarro, Pilar,Marín, Clotilde,Yunta, María J.R.,Cano, Carmen,Campayo, Lucrecia,Martín-Oliva, David,Rosales, María José,Sánchez-Moreno, Manuel
p. 106 - 119
(2015/11/10)

Synthesis of hydroxylactams and esters derived from thalidomide and their antitumor activities
A novel and convenient route for the synthesis of a series of thalidomide derivatives is described. Compound 2 was cyclized with different amines under alkaline condition to obtain 4-nitro substituted phthalimidines 3a-d. Hydroxylactams 4a-d were produced via bromination and hydroxylation. Different acyl chlorides were reacted with hydroxylactams to provide the desired esters 5a-d. All compounds were evaluated by MTT assay for their inhibitory activities against HCT-116, MG-63, MCF-7, HUVEC and HMVEC cell lines in vitro. Most of them showed no obvious cytotoxic effect on normal human cells, compounds 4a-d, 5a2, 5a4, 5a5, 5b2, 5c2 and 5d2 exhibited potent antitumor activities, among which compounds 5a2 and 5b2 were more effective than 5-FU.
Sun, Guanglong,Liu, Xiangchao,Zhou, Heng,Liu, Zenglu,Mao, Zhenmin
p. 1337 - 1342
(2014/06/09)

Rational design of colorimetric reagent for sensitivity and selectivity enhancement for β hydroxy acid of simvastatin
Simvastatin is used in the treatment of hypercholesterolemia as β hydroxy acid of simvastatin (BHA) which inhibits 3-hydroxy methyl glutaryl coenzyme A involved in cholesterol synthesis. The present communication deals with the development of colorimetric method for estimation of BHA through rational design of colorimetric reagent for sensitivity and selectivity enhancement. BHA is an active metabolite as well as impurity of simvastatin, synthesized by alkaline hydrolysis of simvastatin. In the developed colorimetric method, improvement in the sensitivity of quantification of BHA was found to be more than 660 folds. The detector response for BHA in colorimetric method was found to be linear in concentration range of 0.1- 3.2ng/mL. This method was validated using ICH Q2B (R1) guidelines. The reported method is found to be simple, precise, accurate, rapid and economic for quantification of BHA. The colorimetric method can be optimized further for quantification of BHA in simvastatin formulations and in plasma.
Bhatia, Manish S.,Jadhav, Swapnil D.,Dhavale, Rakesh P.,Choudhari, Prafulla B.
p. 496 - 501
(2013/08/23)

Inhibitory properties of 2-substituent-1H-benzimidazole-4-carboxamide derivatives against enteroviruses
A series of novel benzimidazole derivatives were designed, synthesized, and evaluated for their activities against four kinds of enteroviruses, that is, Coxsackie virus A16, B3, B6 and Enterovirus 71 in VERO cells. Strong activities against enterovirus replication and low cytotoxicities were observed in these benzimidazoles generally. The most promising compound was (l)-2-(pyridin-2-yl)- N-(2-(4-nitrophenyl)pentan-3-yl)-1H-benzimidazole-4-carboxamide (16), with a high antiviral potency (IC50 = 1.76 μg/mL) and a remarkable selectivity index (328). These compounds were selected for further evaluation as novel enterovirus inhibitors.
Xue, Fei,Luo, Xianjin,Ye, Chenghao,Ye, Weidong,Wang, Yue
body text
p. 2641 - 2649
(2011/06/11)

LIPOIC ACID AND NITROXIDE DERIVATIVES AND USES THEREOF
The present invention provides bifunctional compounds comprising a poly(ADP-ribose) polymerase (PARP) inhibitor moiety and a reactive oxygen species (ROS) scavenger moiety, more particularly, a lipoic acid or cyclic nitroxide derivative, covalently attached either directly or via a linker, as well as pharmaceutical compositions comprising them. The compounds and pharmaceutical compositions of the invention are useful for prevention, treatment, or management of diseases, disorders and conditions associated with elevated PARP activity or expression.
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Page/Page column 32-34

(2011/12/02)

Dual fluorescent N-Aryl-2,3-naphthalimides: Applications in ratiometric DNA detection and white organic light-emitting devices
A ten element matrix of 5- and 6-substituted-(2,3)-naphthalimides was prepared for the appropriate placement of substituents necessary to promote dual fluorescence (DF). As prescribed by our balanced seesaw photophysical model this matrix yielded nine new DF dyes out of a possible ten compounds. From this set of nine DF dyes, 4-fluoronaphthalic amide (37) was selected as a probe for ratiometric detection of DNA and demonstration of panchromatic emission.
Nandhikonda, Premchendar,Heagy, Michael D.
supporting information; experimental part
p. 4796 - 4799
(2011/01/03)

Synthesis of chiral 3-substituted phthalides by a sequential organocatalytic enantioselective aldol-lactonization reaction. Three-step synthesis of (S)-(-)-3-butylphthalide
(Chemical Equation Presented) The development of efficient methods for the facile construction of important molecular frameworks is an important goal in organic synthesis. Chiral 3-substituted phthalides are widely distributed in a large collection of natural products with broad, potent, and potentially path-pointing biological activities. In this investigation, we have uncovered an unprecedented organocatalytic asymmetric aldol-lactonization reaction of 2-formylbenzoic esters with ketones/aldehydes for convenient construction of the enantioenriched "privileged" scaffold. As a result of the sensitive nature of substrate structures of an organocatalytic enantioselective aldol reaction, after extensive optimization of reaction conditions, catalyst L-prolinamide alcohol IV is identified as the best promoter. Interestingly, it is found that in this reaction, addition of an acid additive PhCO2H can significantly enhance reaction efficiency with use of only as low as 2.5 mol % IV for the process. Moreover, due to the sensitivity of reaction conditions toward a sequential aldol-lactonization process without affecting enantioselectivity and racemization, it is essential to remove the catalyst for the subsequent facile lactonization reaction in the presence of K 2CO3. The aldol-lactonization processes serve as a powerful approach to the preparation of synthetically and biologically important 3-substitued phthalides with a high level of enantioselectivities. A 3-step catalytic asymmetric synthesis of the natural product of 3-butylphthalide is reported.
Zhang, Haoyi,Zhang, Shilei,Liu, Lu,Luo, Guangshun,Duan, Wenhu,Wang, Wei
supporting information; experimental part
p. 368 - 374
(2010/03/30)

Discovery of indenopyrazoles as EGFR and VEGFR-2 tyrosine kinase inhibitors by in silico high-throughput screening
A series of indenopyrazoles 8 and 9 were designed and synthesized as EGFR tyrosine kinase inhibitors by in silico high-throughput screening. Compounds 8b and 8d showed significant inhibition of A431 cell growth (GI50 = 0.062 and 0.057 μM, respectively). Compounds 8b and 9a showed inhibitory activity toward both EGFR and VEGFR-2 (KDR) tyrosine kinases, whereas 8d inhibited VEGFR-2 tyrosine kinase, exclusively.
Usui, Taikou,Ban, Hyun Seung,Kawada, Junpei,Hirokawa, Takatsugu,Nakamura, Hiroyuki
p. 285 - 288
(2008/09/17)

PYRIDAZINE COMPOUNDS AS GLYCOGEN SYNTHASE KINASE 3 INHIBITORS
Disclosed are pyridazine compounds of the formula I which are useful for inhibiting glycogen synthase kinase 3 (GSK-3), methods of making the compounds, compositions containing the compounds, and methods of treatment using the compounds: In formula (I) indicates a single bond or a double bond; X is O, S or N-R5; R1, R2 are independently selected from the group consisting of H, NH2, NH-C1-C6-alkyl, OH, =O, (i.e. a carbonyl group), C1-C6-alkoxy, halogen, methyl, C2-C4-alkyl, C3- C4-cycloalkyl, C3-C4-alkenyl, fluorinated C1-C4-alkyl, fluorinated C3-C4-cycloalkyl, fluorinated C3-C4-alkenyl, formyl, C1-C3-alkylcarbonyl, and an aromatic radical Ar, R1 and R2 together with the carbon atoms, to which they are attached, form a fused, saturated or unsaturated 5-, 6- or 7-membered C-bound carbocyclic or heterocyclic ring comprising 1 heteroatom, selected from nitrogen, oxygen and sulfur as ring member and O, 1 or 2 further heteroatoms, independently selected from O, S and N, as ring members, wherein the fused ring is unsubstituted or may carry 1 , 2 or 3 substituents selected, independently of each other, from the group of radicals R4 as defined below; R3 is hydrogen OH, halogen, CN, nitro, C1-C6-alkyl, fluorinated C1-C6-alkyl, C1-C6- hydroxyalkyl, C1-C6-alkoxy-C1-C6-alkyl, C2-C6-alkenyl, fluorinated C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, fluorinated C3-C7-cycloalkyl, C1-C6-alkoxy, C1-C6- hydroxyalkoxy, C1C6-alkoxy-C1-C6-alkoxy, fluorinated C1-C6-alkoxy, C1-C6- alkylthio, fluorinated-C1-C6 alkylthio, C1C6-alkylsulfinyl, fluorinated C1-C6- alkylsulfinyl, C1-C6-alkylsulfonyl, fluorinated C1-C6 alkylsulfonyl, C1C6- alkylcarbonyl, fluorinated C1C6-alkylcarbonyl, C1-C6-alkylcarbonylamino, fluorinated C1-C6-alkylcarbonylamino, carboxy, C1-C6-alkyloxycarbonyl, fluorinated C1-C6-alkoxycarbonyl, NRaRb, C(O)-NReRf, NH-C(O)-N ReRf, NRaRb-C1-C6-alkylene, O-NRaRb, etc. and wherein R4 and R5 are as defined in the specification and the claims.
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Page/Page column 28; 32-33

(2010/11/25)

Process development for ABT-472, a benzimidazole PARP inhibitor
A nine-step convergent process was developed for the synthesis of ABT-472, a benzimidazole PARP inhibitor. The identity and origin of several impurities were determined, and the process was modified to reduce or eliminate these impurities. A number of safety and control issues were investigated. The original synthesis was shortened to 9 steps and streamlined while maintaining a convergent strategy. A stable salt was selected, and control of the API solid form was established. The process was successfully scaled up to provide 8.5 kg of final product of >99% purity in 33% yield over 9 steps.
Barkalow, Jufang H.,Breting, Jeffrey,Gaede, Bruce J.,Haight, Anthony R.,Henry, Rodger,Kotecki, Brian,Mei, Jianzhang,Pearl, Kurt B.,Tedrow, Jason S.,Viswanath, Shekhar K.
p. 693 - 698
(2012/12/29)

NOVEL DUAL ACTION RECEPTORS ANTAGONISTS (DARA) AT THE AT1 AND ETA RECEPTORS
The present invention relates to new compounds of the formula [Chemical formula should be inserted here. Please see paper copy] wherein R1, R2, R3, and R31 are as specified herein. The invention also relates to a method for preparation thereof, as well as combinations of the new compounds with previously known agents. The invention also relates to the use of the above-mentioned compounds and combinations for the preparation of a medicament for treating hypertension of different kinds, alleviating organ damage of different kinds, treating or preventing diabetic nephropathy, treating endothelin and angiotensin mediated disorders, and treating prostate cancer.
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Page/Page column 252

(2010/11/28)

7-(4,6-dimethoxypyrimidinyl)oxy- and -thiophthalides as novel herbicides: Part 1. CGA 279 233: A new grass-killer for rice
A series of novel types of 7-(4,6-dimethoxypyrimidin-2-yl)oxy - and -thio-3-methyl-1 (3H)-isobenzofuranones were discovered at Dr R Maag AG. From the thio-isobenzofuranyl series, CGA 279 233 - BSI-proposed common name pyriftalid - was chosen for further development as a grass herbicide for use in rice. General synthetic approaches to these new phthalic acid-derived compounds are given, with emphasis on the synthesis of pyriftalid and its physico-chemical behaviour.
Luethy, Christoph,Zondler, Helmut,Rapold, Thomas,Seifert, Gottfried,Urwyler, Bernhard,Heinis, Thomas,Steinruecken, Hans Christian,Allen, James
p. 205 - 224
(2007/10/03)

REACTION OF ARYL ISOTHIOCYANATES WITH PHTHALIC ACID DERIVATIVES
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Kanyonyo, Martial R.,Poupaert, Jacques H.,Leveque, Philippe,Gozzo, Andrea,derpoorten, Kim Van,et al.
p. 55 - 56
(2007/10/03)

Pyrophtalones VII. Synthese et activite anti-inflammatoire de (pyridinyl-4)-2 indanediones-1,3 substituees sur le noyau benzenique et/ou sur l'heterocycle
Pyrophthalones VII.Synthesis and anti-inflammatory activity of 2-(4-pyridinyl)indane-1,3-diones diversely substituted on the benzene ring.Access routes to 2-(1,4-dihydro 4-pyridinylidene) indane-1,3-diones diversely substituted on the benzene ring are studied.The regiospecific attack of these β diketoenamines by alkyl iodides leads to N-substituted compounds.These derivatives may be obtained by any of three possible methods: (1) condensation of 4-methyl pyridine with ethyl phthalates in the absence of catalyst; (2) oxidative condensation of N-alkyl-pyridinium bromides with indane-1,3-diones; (3) aminolysis of 2-(4-4H-pyranylidene) indane-1,3-diones.Pharmacomodulation by the introduction of oxygen or sulfur containing functions (ether, thioether, alcohol, ketone, acid, ester, amide) on the nitrogen of the basic molecule is not very fruitful; only the acetic derivative 19 manifests marked antiinflammatory activity unaccompanied by anti-coagulant action.The presence of chloro, nitro or methoxyl groups on 5 after N-substitution by ethyl or piperidinylethyl groups appears to be more favorable.The most active compound 57 decreases prostaglandin production and leukocyte migration without affecting either cyclooxygenase or 5-lipoxygenase.Its interference, direct or indirect, with phospholipasic A2 activity may be envisaged in particular.Keywords - 2-(4-pyridinyl)indane-1,3-diones / heterocyclic β diketoenamines / partition coefficient / anti-inflammatory activity / mechanism of action
Leblois, Danielle,Piessard, Sylvie,Baut, Guillaume Le,Kumar, Piyush,Brion, Jean-Daniel,et al.
p. 229 - 238
(2007/10/02)

AN IMPROVED PROCEDURE FOR THE SYNTHESIS OF 3-FLUOROANTHRANILIC ACID
3-Ffluoroanthranilic acid is derived in four steps from 3-nitrophthalic acid in 53percent overall yield.
Milner, David J.
p. 485 - 490
(2007/10/02)

Benzocyclobutenes. Part 4. Synthesis of Benzocyclobutene-1,2-diones by Pyrolytic Methods
Oxidation of the cyclic hydrazides prepared from phthalic anhydrides in the presence of anthracene gives the corresponding Diels-Alder adducts which, on flash vacuum pyrolysis, give benzocyclobutene-1,2-dione (BBD) and its 4-chloro, 3,6- and 4,5-dichloro, 4,5-dibromo, and 4,5-dimethyl derivatives in 75-98percent yield.Cyclobuta- and cyclobuta-naphthalene-1,2-dione as well as cyclobuta- and cyclobuta-pyridine-1,2-dione have been prepared similarly; the last three of these diones are very unstable.Cyclobutanaphthalene-1,2-dione has also been made by pyrolysis of benzindene-1,2,3-trione.Attempts to make thiophen and furan analogues of BBD from appropriate anthracene adducts failed as did attempts to make tetrachloro- and tetrabromo-derivatives of BBD by the pyrolysis of tetrahalogenophthalimidosulphoximides.
Gould, Ken J.,Hacker, Nigel P.,McOmie, John F. W.,Perry, David H.
p. 1834 - 1840
(2007/10/02)

Preparation of aminophthalic anhydrides
Processes are described for the preparation of substantially pure aminophthalic anhydrides and for polymerizing these monomers to unmodified and modified improved polyamic acid and polyimides.
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(2008/06/13)