Synthesis of Derivatives of Isophthalamic Acid as X-Ray Contrast Agents

Gb, Hoey; Rd, Rands; DeLaMater, George; Dw, Chapman; Pe, Wiegert

doi:10.1021/jm00337a005

Cited by 14 publications

(4 citation statements)

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“…Scheme 7 depicts the synthesis of several 3,5-disubstituted benzoic acid derivatives. The acid group in 185 51 could be selectively reduced in the presence of an ester using lithium tri-tert-butoxyaluminohydride to give both the aldehydo-(186) and the hydroxymethyl-(187) substituted compounds. The aldehyde was converted to the oxime (188), and both the nitro and hydroxyimino groups were reduced catalytically over palladium to give the diamine 189.…”

Section: Chemistrymentioning

confidence: 99%

“…To a solution of 1.5 g (0.02 mol) of DMF in 30 mL of CH2Cl2 at 0 °C was added 5 mL (0.057 mol) of oxalyl chloride, and the mixture stirred at ice bath temperature for 1 h. The solution was concentrated, and the residue was suspended in 50 mL of THF and 30 mL of MeCN. To this mixture at -30 °C was added dropwise a solution of 4.5 g (0.02 mol) of 3-(methoxycarbonyl)-5-nitrobenzoic acid (185) 51 and 1.6 g (0.02 mol) of pyridine in 10 mL of THF over a 10-min period. The reaction mixture was stirred at -30 °C for 1 h and then treated with a suspension of 0.38 g (0.002 mol) of CuI in 10 mL of THF.…”

Section: 5-bis[(aminoiminomethyl)amino]benzoic Acid (184)mentioning

confidence: 99%

“…The residue was purified by column chromatography on silica gel packed in CHCl3 (5% MeOH in CHCl3) to give 4.9 g (86%) of 199 as a cream-colored solid: mp 80-83 °C; 1 H NMR (400 MHz, CDCl3) δ 1. 51…”

Section: 5-bis[(aminoiminomethyl)amino]benzoic Acid (184)mentioning

confidence: 99%

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Design and Synthesis of Benzoic Acid Derivatives as Influenza Neuraminidase Inhibitors Using Structure-Based Drug Design

Chand

Bantia

et al. 1997

J. Med. Chem.

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A series of 94 benzoic acid derivatives was synthesized and tested for its ability to inhibit influenza neuraminidase. The enzyme-inhibitor complex structure was determined by X-ray crystallographic analysis for compounds which inhibited the enzyme. The most potent compound tested in vitro, 5 (4-acetylamino)-3-guanidinobenzoic acid), had an IC50 = 2.5 x 10(-6) M against N9 neuraminidase. Compound 5 was oriented in the active site of the neuraminidase in a manner that was not predicted from the reported active site binding of GANA (4) with neuraminidase. In a mouse model of influenza, 5 did not protect the mice from weight loss due to the influenza virus when dosed intranasally.

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Section: Chemistrymentioning

confidence: 99%

Section: 5-bis[(aminoiminomethyl)amino]benzoic Acid (184)mentioning

confidence: 99%

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Design and Synthesis of Benzoic Acid Derivatives as Influenza Neuraminidase Inhibitors Using Structure-Based Drug Design

Chand

Bantia

et al. 1997

J. Med. Chem.

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“…1978, 21, 930-935. erally in accordance with those obtained by the PCA test, with some exceptions. In the series of N-[3,5-(COOH)2phenyl]benzamide derivatives (compounds 1-21), the derivatives in which Ri consists of alkyl groups (compounds 2-4), electron donor groups (compounds 5-12), or halogen groups (compounds [13][14][15][16] are all barely effective or ineffective at all. In fact, among these derivatives the most effective is compound 12, a 4-OPr benzamido derivative, that exhibits an ID50 of only 78 mg/kg.…”

Section: Table III Further Cytoprotective Evaluation Ofmentioning

confidence: 99%

Antiallergic and cytoprotective activity of new N-phenylbenzamido acid derivatives.

Makovec¹,

Peris²,

Revel³

et al. 1992

J. Med. Chem.

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A series of new N-phenylbenzamido acid derivatives was synthesized and evaluated for their ability to inhibit the IgE-mediated passive cutaneous anaphylaxis in the rat (PCA), as well as for their capacity to inhibit gastric mucosal damage induced by the oral administration of absolute alcohol in the rat. Some of these new derivatives exhibit potent antiallergic and cytoprotective activity, 20-80 times higher than that of the reference, disodium cromoglycate (DSCG). Structure-activity relationships are discussed. The antiallergic activity of one of the more potent compounds of this series, i.e. 4-(1H-tetrazol-5-yl)-N-[4-(1H-tetrazol-5-yl)phenyl]benzamide (compound 44, CR 2039) was further evaluated in vivo. This compound antagonizes the bronchoconstriction induced by aerosolized ovalbumin in both anesthetized and conscious IgE sensitized guinea pigs with ID50 of 3.7 mg/animal (tracheal insufflation) and 20 mg/kg (im). Further cytoprotective effects were evaluated in gastric ulcer models induced by the acute oral administration of hypertonic sodium chloride solution or by acetic acid and by the subchronic administration of glucose in fasted animals. In the models used experimentally CR 2039 is effective, whereas DSCG seems to be devoid of any protective activity. Such a potent antiallergic and mucosal protectant could provide a new potential agent in the therapy of atopic allergic diseases.

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Radiopaques

Lin

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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Lin, Youlin (Mallinckrodt Medical, Inc.). Medical examination of soft tissues or organs by nonsurgical means often requires the introduction of a special agent that makes the detection system responsive to detail in the tissue of interest. Radiopaques, often called x‐ray contrast media, are examples of such diagnostic agents. Radiopaques are categorized according to specific applications, such as angiography, urography, myelography, cholecystography, cholangiography, gastrointestinal radiography, computed tomography, arthrography, and hysterosalpingography. The importance, chemistry, and kinds of radiopaques developed for the types of medical imaging are presented. The evolution of research efforts from high osmolality contrast media (HOCM) to low osmolality contrast media (LOCM) is emphasized. Historical perspectives, cost considerations, and future outlooks in contrast media development are briefly outlined. Physical constants, such as osmolality, water solubility, viscosity and partition coefficient, and median lethal dose in animal studies are cited and compared for selected contrast agents. Sources are listed for commercial radiopaque suppliers in the United States. Vol. 20, pp. 906–930, 129 refs. to December 1995.

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Synthesis of Derivatives of Isophthalamic Acid as X-Ray Contrast Agents

Cited by 14 publications

References 1 publication

Design and Synthesis of Benzoic Acid Derivatives as Influenza Neuraminidase Inhibitors Using Structure-Based Drug Design

Design and Synthesis of Benzoic Acid Derivatives as Influenza Neuraminidase Inhibitors Using Structure-Based Drug Design

Antiallergic and cytoprotective activity of new N-phenylbenzamido acid derivatives.

Radiopaques

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