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Detail of "53164-05-9"

  • MSDS Download
  • CAS Number:
  • 53164-05-9
  • Name:

  • 1H-Indole-3-aceticacid, 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-, carboxymethyl ester

  • Superlist Name:
  • Acemetacin
  • Molecular Structure:
  • Formula:
  • C21H18ClNO6
  • Molecular Weight:
  • 415.83
  • Synonyms:
  • 1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-aceticacid carboxymethyl ester;1-(p-Chlorobenzoyl)-5-methoxy-2-methylindole-3-aceticacid carboxymethyl ester;2-[2-[1-[(4-Chlorophenyl)carbonyl]-5-methoxy-2-methylindol-3-yl]acetyloxy]aceticacid;Acemet;Acemethacin;Acemix;Emflex;K 708;Rantudil;Rheumibis;Rheutrop;Solart;TV 1322;TVX 1322;
  • EINECS:
  • 258-403-4
  • Density:
  • 1.36 g/cm3
  • Melting Point:
  • 151.5 °C
  • Boiling Point:
  • 565.5 °C at 760 mmHg
  • Flash Point:
  • 295.8 °C
  • Appearance:
  • Light yellow solid
  • Hazard Symbols:
  • VeryT+
  • Risk Codes:
  • 26/27/28
  • Safety:
  • 22-25-36/37/39-45 Details
  • Transport Information:
  • UN 2811
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ACEMETACIN

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CAS No.53164-05-9 Acemetacin

Chemical Name: ACEMETACIN CAS No. 53164-05-9 Molecular Formula: C21H18ClNO6 Formula Weight: 415.82 Property mp : 151.5°C Safety Hazard Codes : T+ Risk Statements : 26/27/28 Safety Statements : 22-25-36/37/39-45

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Reference

Reactions of antiinflammatory indole derivatives with singlet oxygen
Reactions of antiinflammatory indole derivatives with singlet oxygen. I. Participation of reactive oxygen species in the mechanism of prostaglandin synthesis. Duchstein, Hans Juergen (Pharm. Inst., Freie Univ. Berlin, Berlin 1000/33, Fed. Rep. Ger.). Arch. Pharm. (Weinheim, Ger.), 318(2), 127-34 (German) 1985. CODEN: ARPMAS. ISSN: 0365-6233. DOCUMENT TYPE: Journal CA Section: 1 (Pharmacology) Section cross-reference(s): 2 The reaction of 1O2 with antiinflammatory indole derivs., such as indomethacin [53-86-1] and acemetacin [53164-05-9], which inhibit prostaglandin synthesis, are described. The initial step was a (2+2)-cycloaddn. of 1O2 as electrophilic agent onto the indole to form a dioxetane. This intermediate reacted by ring opening to yield o-acylanilides (in the case of indomethacin and acemetacin, [2-(4-chlorobenzoylamino)-5-methoxy]benzoyl-2-acetoxyacetic acid [95480-53-8], [2-(4-chlorobenzoylamino)-5-methoxy]benzoyl-2-acetic acid Me ester [95480-54-9], 2-acetyl-N-(4-chlorobenzoyl)-4-methoxyaniline [95480-55-0], 1,2-diacetyl-4-methoxyaniline [52417-34-2]) and the substituted ester N-(4-chlorobenzoyl)-5-methoxy-anthranilic acid Me ester [95480-56-1]. Recyclization led to the benzoxazinone 2-(4-chlorophenyl)-6-methoxy-4H-3,1-benzoxazin-4-one [95480-57-2]. The lactone 8-(4-chlorobenzoyl)-3a-hydroxy-5-methoxy-8a-methyl-2-oxo-2,3,3a,8 a-tetrahydro-1H-furo[2,3-b]indole [95480-58-3] was also isolated. These in vitro reactions could be relevant to the mechanism of prostaglandin synthesis inhibition if 1O2 is a reactive O species involved in the enzymic aspect of prostaglandin synthesis.
1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-3-indoleacetoxyacetic acid
1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-3-indoleacetoxyacetic acid. Boltze, Karl Heinz (Troponwerke G.m.b.H. und Co. K.-G., Fed. Rep. Ger.). Ger. Offen. DE 3206888 A1 15 Sep 1983, 15 pp. (German). (Germany). CODEN: GWXXBX. CLASS: IC: C07D209-12. APPLICATION: DE 82-3206888 26 Feb 1982. DOCUMENT TYPE: Patent CA Section: 27 (Heterocyclic Compounds (One Hetero Atom)) The title compd. I (R = CH2CO2H) was prepd. in greater purity and in a simpler manner than by known methods, by treating I (R = 2,4,5-Cl3C6H2, Cl5C6, F5C6) with HOCH2CO2R1 (R1 = H, ammonium) in an inert solvent at -10 to +80°. Treating I (R = H) and 2,4,5-Cl3C6H2OH in CH2Cl2 with dicyclohexylcarbodiimide at -10° and warming 1 h to room temp.There are some commonly used reagents with their cas registry numbers 88258-09-7 and 53164-05-9 in this article. gave 100% I (R = 2,4,5-Cl3C6H2) which was treated with HOCH2CO2H in DMF with NEt3 18 h at room temp., then 2.5 h at 60°, finally treated with HN(CHMe2)2 in CH2Cl2 to give I [R = CH2CO2- H2N+(CHMe2)2]. This in aq. Me2CO was treated with N HCl to give 61% I (R = CH2CO2H). .
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