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. Author manuscript; available in PMC: 2013 Jan 31.
Published in final edited form as: J Med Chem. 2013 Jan 4;56(2):589–590. doi: 10.1021/jm301634c

Correction

PMCID: PMC3560427  NIHMSID: NIHMS433463  PMID: 23289730

Structure–Activity Relationship Study of N6-(2-(4-(1H-Indol-5-yl)piperazin-1-yl)ethyl)-N6-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine Analogues: Development of Highly Selective D3 Dopamine Receptor Agonists along with a Highly Potent D2/D3 Agonist and Their Pharmacological Characterization

Mark Johnson,† Tamara Antonio,‡ Maarten E. A. Reith,‡,§ and Aloke K. Dutta*,†

  1. Abstract: Structure of (-)-19 should include a chlorine atom at the 4-position of the indole ring. Structure should be:

    graphic file with name nihms433463f1.jpg

  2. Scheme 2: The following structures should include a chlorine atom at the 4-position of the indole ring: 17, (±)-18, (−)-18, (+)-18, (±)-19, (–)-19, (+)-19, 20 and 21.

    Revised Scheme 2

    graphic file with name nihms433463f2a.jpg

    graphic file with name nihms433463f2b.jpg

    Scheme 2. Reagents and conditions: (a) triisopropylsilyl chloride, NaH, THF; (b) 4, PdCl 2[P(o-tol)3]2, Nao tBu, xylenes, reflux; (c) CF 3COOH, CH 2Cl2; (d) (2-bromo-ethoxy)-tert-butyl-dimethy silane, K2CO3, CH3CN, reflux; (e) (Boc)2O, DMAP, THF; (f) n-Bu4NF, THF; (g) (COCl)2, DMSO Et3N, CH2Cl2, −78 °C-rt; (h) (±), (−) or (+)-pramipexole, Na(OAc)3BH, CH2Cl2; (i) CF3COOH, CH2Cl2; (j) 2, Na(OAc)3BH, CH2Cl2; (k) aq. HBr (48%), reflux.

  3. Supporting Information: Elemental analysis adjusted for the final compounds and mass spectral data:
    • (±)-19- C24H33ClN6S·3CF3COOH.
      Calculated: Carbon- 44.11, Hydrogen- 4.45, Nitrogen- 10.31
      Found: Carbon- 44.58, Hydrogen- 4.93, Nitrogen- 10.57
      MS: m/z : 473.
    • (−)-19- C24H33ClN6S·3CF3COOH
      Calculated: Carbon- 44.20, Hydrogen- 4.45, Nitrogen- 10.31
      Found: Carbon- 44.55, Hydrogen- 4.55, Nitrogen- 10.54
      MS: m/z : 473.
    • (+)-19- C24H33ClN6S·3CF3COOH
      Calculated: Carbon- 44.20, Hydrogen- 4.45, Nitrogen- 10.31
      Found: Carbon- 43.86, Hydrogen- 4.69, Nitrogen- 10.36
      MS: m/z : 473.
    • 21- C27H35ClN4O·3HBr.3H2O
      Calculated: Carbon- 42.46 Hydrogen-5.81 Nitrogen- 7.34
      Found: Carbon- 42.44 Hydrogen- 5.82 Nitrogen-7.36
    • 20- C33H45ClN4O3
      MS: m/z: 581

Table 1.

Empirical formula of compounds with elemental analysis data.

Compound number Calculated Found
C H N C H N
9b, C28H46Cl4N4O3 53.51 7.38 8.91 52.96 7.37 8.34
(±)-41, C32H41F9N6O8S 45.71 4.92 10.00 45.23 4.92 9.50
(±)-42, C33H49F9N6O11S 43.61 5.43 9.25 44.02 5.03 8.64
(+)-45, C25H42Cl4N6O3S 46.30 6.53 12.96 46.29 6.77 11.80
(±)-46, C25H42Cl4N6O3S 46.30 6.53 12.96 47.16 6.76 12.74
(+)-46, C25H40Cl4N6O2S 47.62 6.39 13.33 48.02 6.90 13.05
48, C29H54Cl4N6O6S 46.03 7.19 11.11 46.29 6.77 11.80
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