cas 6295-21-2, 3-Chlorophthalide | Articles data

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OXOBENZINDOLIZINOQUINOLINES AND USES THEREOF
The synthesis of aromathecins, substituted 12H-5,l la-diazadibenzo[b,h]fluoren- 11 -ones is described. Use of these cytotoxic compounds and pharmaceutical compositions containing them for the treatment of cancer is described. Two novel processes for the synthesis of this system and a series of 14-substituted aromathecins as novel cytotoxic, topoisomerase I poisons are described.
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Page/Page column 30

(2009/12/23)

Synthesis and biological evaluation of 14-(aminoalkyl-aminomethyl)aromathecins as topoisomerase I inhibitors: Investigating the hypothesis of shared structure-activity relationships
The aromathecin topoisomerase I (top1) inhibitors offer promising scaffolds for the development of novel cancer chemotherapeutics. They are 'composites' of the camptothecin and indenoisoquinoline top1 inhibitors. Interestingly, some structure-activity relationship (SAR) overlap between the aromathecins and the indenoisoquinolines has been observed. For both classes, placement of certain polar groups in similar regions of the heteroaromatic system improves top1 inhibitory and antiproliferative activities. A series of water-soluble aromathecins substituted at position 14 with diaminoalkanes of various lengths has been prepared. These compounds all possess similar antiproliferative potency, but a general trend is observed: aromathecins with longer diaminoalkane substituents (>6 carbons) possess lower anti-top1 activity than their smaller counterparts (2-4 carbons), presumably as a result of unfavorable hydrophobic interactions. This trend is also noted with the indenoisoquinolines, revealing additional SAR overlap that supports the hypothesis that there is a 'universal' top1 inhibitor SAR.
Cinelli, Maris A.,Cordero, Brenda,Dexheimer, Thomas S.,Pommier, Yves,Cushman, Mark
scheme or table
p. 7145 - 7155
(2010/03/01)

Design, synthesis, and biological evaluation of 14-substituted aromathecins as topoisomerase I inhibitors
The aromathecin or "rosettacin" class of topoisomerase I (top1) inhibitors is effectively a "composite" of the natural products camptothecin and luotonin A and the synthetic indenoisoquinolines. The aromathecins have aroused considerable interest following the isolation and total synthesis of 22-hydroxyacuminatine, a rare cytotoxic natural product containing the 12H-5,11a-diazadibenzo[b,h]fluoren-11-one system. We have developed two novel syntheses of this system and prepared a series of 14-substituted aromathecins as novel antiproliferative topoisomerase I poisons. These inhibitors are proposed to act via an intercalation and "poisoning" mechanism identical to camptothecin and the indenoisoquinolines. Many of these compounds possess greater antiproliferative activity and anti-top 1 activity than the parent unsubstituted compound (rosettacin) and previously synthesized aromathecins, as well as greater top1 inhibitory activity than 22-hydroxyacuminatine. In addition to potentially aiding solubility and localization to the DNA-enzyme complex, nitrogenous substituents located at the 14-position of the aromathecin system have been proposed to project into the major groove of the top1-DNA complex and hydrogen-bond to major-groove amino acids, thereby stabilizing the ternary complex.
Cinelli, Maris A.,Morrell, Andrew,Dexheimer, Thomas S.,Scher, Evan S.,Pommier, Yves,Cushman, Mark
experimental part
p. 4609 - 4619
(2009/07/04)

The investigation of nucleophilic reactions of 3 -bromo/chloro phthalide with amines
The reaction of 3-bromo/chloro phthalide 1a/b with secondary amines in polar solvents gives the corresponding amides of 2-formylbenzoic acid, while in nonpolar solvents gives 3-aminophthalides. The reaction of 1a/b with aromatic primary amines gives 3-arylaminophthalides, while with aliphatic primary amines 3-hydroxyphthalimidines are obtained.
Desai,Chaphekar,Samant
p. 810 - 813
(2007/10/03)

Pseudoacids. II. 2-Acylbenzoic Acid Derivatives
Structures of derivatives of cyclic o-acylbenzoic acids, including the chloride, endo- and exocyclic amides, esters and anhydrides, are examined. 3-Chloro-1(3H)-isobenzofuranone (1), orthorhombic, Pbca, a = 11.616 (5), b = 8.120 (3), c = 15.640 (9) A; 3-methoxy-3-phenyl-1(3H)-isobenzofuranone (3), orthorhombic, P212121, a = 6.923 (2), b = 8.291 (4), c = 21.551 (8) A; 3-hydroxy-3-phenyl-N-propyl-1(3H)-isoindolone (4), orthorhombic, P212121, a = 8.662 (4), b = 9.551 (7), c = 17.649 (14) A; 3-(N-morpholino)-1(3H)-isobenzofuranone (5), triclinic, P1, a = 6.172 (4), b = 11.163 (7), c = 17.33 (2) A, α = 105.91 (6), β = 99.85 (6), γ = 97.57 (5)°; 3-(2′-benzoylbenzoyloxy)-3-phenyl-1(3H)-isobenzofuranone (7), triclinic, P1, a = 9.694 (3), b = 10.505 (4), c = 11.163 (4) A°, α = 80.58 (3), β = 80.41 (3), γ = 76.49 (3)°; bis[1(3H)-isobenzofuranone-3-yl]ether (8), monoclinic, I2/a, a = 15.31 (2), b = 6.111 (12), c = 28.30 (5) A, β = 101.61 (12)°. An open oxoacid tertiary amide is also described: N-morpholino 2′-benzoylbenzamide (6): monoclinic, P21/c, a = 6.844 (4), b = 15.696 (8), c = 14.154 (7) A, β = 99.43 (4)°. Pseudoacid derivatives form planar isobenzofuran and isoindole rings, and the former aldehyde/ketone carbon-heteroatom endocyclic and exocyclic bond distances show bond length variations which correlate with the relative basicities of the attached groups. Structures of both endocyclic and exocyclic nitrogen pseudoamides are reported as well as examples of the normal-pseudoanhydride and the dipseudoanhydride.
Valente, Edward J.,Martin, Samuel B.,Sullivan, Larry D.
p. 264 - 276
(2007/10/03)

Intramolecular Diels-Alder reaction of 1-aminoisobenzofurans: Application to the synthesis of benzo [c]phenanthridines
Intramolecular Diels-Alder reactions of 1-aminoisobenzofurans give benzo[c)phenanthridines. The reactive intermediates are generated from o- (diazomethyl)benzamides.
Bernabe, Pablo,Castedo, Luis,Dominguez, Domingo
p. 9785 - 9788
(2007/10/03)

ELECTROCHEMICAL REDUCTION OF PHTHALYL CHLORIDE. A NEW ROUTE FOR THE SYNTHESIS OF 3-SUBSTITUTED PHTHALIDES
The cathodic reduction, under various conditions, of phthalyl chloride enables efficient synthesis of (E)-biisobenzofuranyliden-3,3'-dion(4), (2)-benzopyrano - benzopyrano-6,12-dione (7), 3-chlorophtalide (8), phtalide (9), or (E)-3 phtalide (12); the structure of the latter compound was confirmed by X-ray crystallography.
Guirado, Antonio,Barba, Fructuoso,Hursthouse, Michael B.,Martinez, Antonio,Arcas, Aurelia
p. 4063 - 4066
(2007/10/02)

Effect of Nucleophilicity and Leaving Group Ability on the SN2 Reactions of Amines with (Acyloxy)alkyl α-Halides: A Product Distribution Study
The course of the reaction of amines with (acyloxy)alkyl α-halides has been found to depend on the nucleophilicity of the amines and the leaving group ability of the halides.More nucleophilic amines tended to give acylated products 2 from the reaction while less nucleophilic amines gave alkylated products 3.The use of a better leaving group also tended to favor the formation of a greater amount of alkylated product.These results have been compared to the observations of Westaway on the effect of leaving group ability and nucleophilicity on the bond lengths in the transit ion state of SN2 reactions.In addition, secondary amines have been shown to cause the rearrangement of 2-formylbenzamides to 3-amino-1(3H)-isobenzofuranones.
Sloan, Kenneth B.,Koch, Suzanne A. M.
p. 635 - 640
(2007/10/02)

Method of cleaving siloxanes
A process for the preparation of a halogen silane and an aromatic compound having at least one --C=O-- of STR1 group, while simultaneously effecting cleavage of a siloxane by contacting a compound having at least one aromatically bound mono and/or dihalogen methylene group or an aromatic compound having a mono-, di and or trihalogen methyl group of the formula STR2 wherein the aromatic moiety can be optionally otherwise substituted, with a siloxane of the formula STR3 wherein each R moiety is independently selected from the group consisting of halogen, alkyl, alkenyl and O-SiR3, wherein such R moiety is halogen, alkyl or alkenyl, wherein at least two of the R moieties can, together with the silicon atom to which they are attached, form a ring, at an elevated temperature in the presence of a catalytic amount of a metal or a metal compound, which metal is of the sub-group of elements or of the 5th principal group of the periodic system of the elements, together with a proton donor, or in the presence of a catalytic amount of an oxygen acid.
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(2008/06/13)

Aspects of Tautomerism: Part X - Neighbouring Group Effects on the Structure and Reactivity Patterns of Acid Chlorides
The influence of neighbouring groups on the structure and reactivity patterns of over one hundred acid chlorides derived from γ- and δ-keto acids, 1,2- and 1,3-dicarboxylic acid half-esters and diacid chlorides have been examined.Contrary to reports in the literature, text books and monographs, evidence has been obtained for the non-existence of tautomerism between the isomeric pairs of either acid chlorides or half-ester acid chlorides.ce.
Bhatt, M. Vivekananda,El Ashry, Shaker H.,Somayaji, Vishwanatha
p. 473 - 486
(2007/10/02)

Method of preparing phthalide
An improvement in a process for preparing phthalide by reacting chlorophthalide with hydrogen in the presence of a catalyst at a temperature between 50° and 350° C., the improvement residing in carrying out the process in the absence of a hydrogen chloride acceptor, flowing the chlorophthalide continuously in fluid form through a solid catalyst bed in a reactor, passing the hydrogen through in such an excess so as to sweep off the hydrogen chloride formed and withdrawing phthalide in fluid form.
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(2008/06/13)