Sundar Jeyaperumal Kalyana, Rajesh Stephen Michael, Sivamani Jeyaraman, Perumal Subbu, Natarajan Subramanian
Department of Physics, Madurai Kamaraj University, Madurai - 625 021, India.
Chem Cent J. 2011 Jul 26;5(1):45. doi: 10.1186/1752-153X-5-45.
The spiro- indole-pyrrolidine ring system is a frequently encountered structural motif in many biologically important and pharmacologically relevant alkaloids. The derivatives of spirooxindole ring systems are used as antimicrobial, antitumour agents and as inhibitors of the human NKI receptor besides being found in a number of alkaloids like horsifiline, spirotryprostatin and (+) elacomine. The recently discovered small-molecule MDM2 inhibitor MI-219 and its analogues are in advanced preclinical development as cancer therapeutics.
In the crystal structures of the two organic compounds, 4'-Nitro-3',5'-diphenylspiro[indoline-3,2'-pyrrolidin]-2-one and 3'-(4-Methoxyphenyl)- 4'-nitro -5'-phenylspiro[indoline-3,2'-pyrrolidin]-2-one, N-H···O hydrogen bonds make the R22 (8) ring motif. Further, the structures are stabilized by intermolecular hydrogen bonds.
The crystal structures of 4'-Nitro-3',5'-diphenylspiro[indoline-3,2'-pyrrolidin]-2-one and 3'-(4-Methoxyphenyl)- 4'-nitro -5'-phenylspiro[indoline-3,2'-pyrrolidin]-2-one have been investigated in detail. In both the compounds, the R22(8) motif is present. Due to the substitution of methoxyphenyl instead of phenyl ring, the entire configuration is inverted with respect to the 2-oxyindole ring.
螺-吲哚-吡咯烷环系统是许多具有重要生物学意义和药理学相关性的生物碱中常见的结构基序。除了在许多生物碱如马钱子碱、螺旋色胺酮和（+）伊拉可明中发现外，螺氧化吲哚环系统的衍生物还用作抗菌、抗肿瘤药物以及人类NKI受体的抑制剂。最近发现的小分子MDM2抑制剂MI-219及其类似物作为癌症治疗药物正处于临床前开发的后期阶段。
在两种有机化合物4'-硝基-3',5'-二苯基螺[吲哚啉-3,2'-吡咯烷]-2-酮和3'-（4-甲氧基苯基）-4'-硝基-5'-苯基螺[吲哚啉-3,2'-吡咯烷]-2-酮的晶体结构中，N-H···O氢键形成了R22(8)环基序。此外，这些结构通过分子间氢键得以稳定。
已详细研究了4'-硝基-3',5'-二苯基螺[吲哚啉-3,2'-吡咯烷]-2-酮和3'-（4-甲氧基苯基）-4'-硝基-5'-苯基螺[吲哚啉-3,2'-吡咯烷]-2-酮的晶体结构。在这两种化合物中，均存在R22(8)基序。由于用甲氧基苯基取代了苯环，整个构型相对于2-氧化吲哚环发生了反转。
