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Acetamide, N-​[2-​[7-​(cyclohexylmethyl)​-​1,​6-​dihydro-​2H-​indeno[5,​4-​b]​furan-​8-​yl]​ethyl]​-

339.47, C22 H29 N O2

cas 1287785-08-3

Melatonin MT2 Agonists


Treatment of Sleep Disorders,

  • Melatonin (N-acetyl-5-methoxytryptamine), which is a hormone synthesized and secreted principally in the pineal gland, increases in dark circumstances and decreases in light circumstances. Melatonin exerts suppressively on pigment cells and the female gonads, and acts as a synchronous factor of biological clock while taking part in transmittance of photoperiodic code. Therefore, melatonin is expected to be used for the therapy of diseases related with melatonin activity, such as reproduction and endocrinic disorders, sleep-awake rhythm disorders, jet-lag syndrome and various disorders related to aging, etc.
  • Recently, it has been reported that the production of melatonin melatonin could reset the body’s aging clock (see Ann. N. Y. Acad. Sci., Vol. 719, pp. 456-460 (1994)). As previously reported, however, melatonin is easily metabolized by metabolic enzymes in vivo (see Clinical Examinations, Vol. 38, No. 11, pp. 282-284 (1994)). Therefore, it cannot be said that melatonin is suitable as a pharmaceutical substance.
  • Various melatonin agonists and antagonists such as those mentioned below are known.

    • (1) EP-A-578620 discloses compounds of:


      • Figure 00020001
      • (2) EP-A-420064 discloses a compound of:
        Figure 00020002
      • (3) EP-A-447285 discloses a compound of:
        Figure 00020003
      • (4) EP-A-662471 discloses a compound of:
        Figure 00020004
      • (5) EP-A-591057 discloses a compound of:
        Figure 00020005
      • (6) EP-A-527687 discloses compounds of:
        Figure 00030001

        X=S, 0, Y=CH
        X=0, NH, Y=N

      • (7) EP-A-506539 discloses compounds of:
        Figure 00030002
    • Tricyclic or more poly-cyclic compounds with a cyclic ether moiety, such as those mentioned below, are known.

      • (1) Compounds of:
        Figure 00030003

        are disclosed in Tetrahedron Lett., Vol. 36, p. 7019 (1995).

      • (2) Compounds of:
        Figure 00040001
        Figure 00040002

        are disclosed in J. Med. Chem., Vol. 35, p. 3625 (1992).

      • (3) Compounds of:
        Figure 00040003

        are disclosed in Tetrahedron, Vol. 48, p. 1039 (1992).

      • (4) Compounds of:
        Figure 00040004

        are disclosed in Tetrahedron Lett., Vol. 32, p. 3345 (1991).

      • (5) A compound of:
        Figure 00050001

        is disclosed in Bioorg. Chem., Vol. 18, p. 291 (1990).

      • (6) A compound of:
        Figure 00050002

        is disclosed in J. Electroanal. Chem. Interfacial Electrochem., Vol. 278, p. 249 (1990).





Highly Potent MT2-Selective Agonists

J. Med. Chem., 2011, 54 (9), pp 3436–3444
DOI: 10.1021/jm200221q

N-{2-[7-(Cyclohexylmethyl)-1,6-dihydro-2H-indeno[5,4-b]furan-8-yl]ethyl}acetamide (15)

By a similar procedure that described for 8, 15 (79%) was obtained as a white solid; mp 133−134 °C (EtOAc/hexane).
1H NMR (CDCl3) δ 0.82−1.03 (2H, m), 1.06−1.32 (3H, m), 1.42−1.78 (6H, m), 1.96 (3H, s), 2.32 (2H, d, J = 7.2 Hz), 2.74 (2H, t, J = 7.2 Hz), 3.26 (2H, s), 3.32−3.52 (4H, m), 4.59 (2H, t, J = 8.6 Hz), 5.60 (1H, s), 6.59 (1H, d, J = 7.9 Hz), 7.11 (1H, d, J= 7.9 Hz).
MS (ESI) m/z 340 (M + H)+. Anal. (C22H29NO2) C, H, N.

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