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Crystal Growth and Design
Volumn 9, Issue 4, 2009, Pages 1655-1657
Multi-component hydrogen-bonding assembly of a pharmaceutical agent pamoic acid with piperazine or 4,4 -bipyridyl: A channel hydrated salt with multiple-helical motifs vs a bimolecular cocrystal
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EID: 65249147115     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg801393a     Document Type: Article
Times cited : (87)
References (43)
  • 2
    • 0035498334 scopus 로고    scopus 로고
    • (b) Albrecht, M. Chem. Rev. 2001, 101, 3457-3497.
    • (2001) Chem. Rev , vol.101 , pp. 3457-3497
    • Albrecht, M.1
  • 31
    • 65249186412 scopus 로고    scopus 로고
    • Pamoic acid is a pharmaceutically acceptable organic acid and is generally applied to obtain long-acting pharmaceutical formulations by decreasing the solubility of basic drags. That is to say, the main pharmaceutical interest in salts with pamoic acid is that they are usually of low solubility, and hence make attractive forms of a drug substance in controlled release formulations. Recently, pamoic acid is also of great crystallographic interests see ref 15 and references cited therein
    • Pamoic acid is a pharmaceutically acceptable organic acid and is generally applied to obtain long-acting pharmaceutical formulations by decreasing the solubility of basic drags. That is to say, the main pharmaceutical interest in salts with pamoic acid is that they are usually of low solubility, and hence make attractive forms of a drug substance in controlled release formulations. Recently, pamoic acid is also of great crystallographic interests (see ref 15 and references cited therein).
  • 33
    • 65249183061 scopus 로고    scopus 로고
    • Preparation of 1. H2PA (38.8 mg, 0.1 mmol) was dissolved in ethanol (5 mL, to which a water solution of PIPO (0.5 mL, 0.2 mmol/L) was added with stirring. The mixture was then filtered to a test tube and left to stand at room temperature. Yellow lamellar crystals of 1 were obtained after ca. two weeks in a yield of 75, 39.6 mg, based on PIPO, Anal. Calcd for C27H32N2O9: C,'61.35; H, 6.10; N, 5.30, Found: C, 61.25; H, 6.17; N, 5.38, IR cm-1, 3353b, 3029m, 2812w, 2619w, 2438w, 1628s, 1555m, 1506s, 1446vs, 1385vs, 1325vs, 1239m, 1200m, 1153m, 1091s, 1010s, 983m, 950m, 906m, 864m, 81lm, 753s, 597s, 551w, 523w, 490m. Preparation of 2: The same synthetic route as that of 1 was used, except that PIPO was replaced b
    • -1): 3431b, 3060w, 2374w, 1667s, 1601s, 1507m, 1444s, 1409m, 1358vs, 1318s, 1230m, 1200m, 1156m, 1088w, 1060s, 1007m, 960w, 927w, 853w, 807vs, 749s, 707m, 634m, 596w, 526w, 494m.
  • 34
    • 65249161052 scopus 로고    scopus 로고
    • int = 0.0383, S = 1.065, R = 0.0374, and wR = 0.0964.
    • int = 0.0383, S = 1.065, R = 0.0374, and wR = 0.0964.
  • 35
    • 65249145979 scopus 로고    scopus 로고
    • int = 0.0299, S = 1.028, R = 0.0427, and wR = 0.1035.
    • int = 0.0299, S = 1.028, R = 0.0427, and wR = 0.1035.
  • 36
    • 65249109178 scopus 로고    scopus 로고
    • The CSD (Cambridge Structural Database) refcodes are JAWXEL, JAWX1P, JAWXOV, JAWXUB, JAWYAI, MEBGOQ, TABMAK, and QEXJEJ. Compounds 1, 2, and 7 reported in ref 15 are also included, whereas others with pamoate being involved in metal coordination are not considered.
    • The CSD (Cambridge Structural Database) refcodes are JAWXEL, JAWX1P, JAWXOV, JAWXUB, JAWYAI, MEBGOQ, TABMAK, and QEXJEJ. Compounds 1, 2, and 7 reported in ref 15 are also included, whereas others with pamoate being involved in metal coordination are not considered.
  • 37
    • 65249132905 scopus 로고    scopus 로고
    • Interestingly, the structure of pamoic acid itself (determined from X-ray powder diffraction data, see ref 21) has a similar conformation to that of 1 see Figure S6, Supporting Information, suggesting its potential for helical assembly
    • Interestingly, the structure of pamoic acid itself (determined from X-ray powder diffraction data, see ref 21) has a similar conformation to that of 1 (see Figure S6, Supporting Information), suggesting its potential for helical assembly.
  • 40
    • 25844507117 scopus 로고    scopus 로고
    • Haynes, D. A.; Jones, W.; Motherwell, W. D. S. CrystEngComm 2005, 7, 538-543.
    • (b) Haynes, D. A.; Jones, W.; Motherwell, W. D. S. CrystEngComm 2005, 7, 538-543.
  • 42
    • 65249122416 scopus 로고    scopus 로고
    • One DMF solvate of pamoic acid has been reported in ref 15.
    • One DMF solvate of pamoic acid has been reported in ref 15.
  • 43
    • 65249146528 scopus 로고    scopus 로고
    • At present, it seems impossible to make a full CSD (Cambridge Structural Database) search to establish whether the interesting multiple-helical motifs in 1 are unique
    • At present, it seems impossible to make a full CSD (Cambridge Structural Database) search to establish whether the interesting multiple-helical motifs in 1 are unique.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.