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Chemical Compound Review

Indoline     2,3-dihydro-1H-indole

Synonyms: Azaindane, Dihydroindole, Indoline, 19, PubChem7502, SureCN5629, ...
 
 
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Disease relevance of indoline

  • The design and enzyme-bound crystal structure of indoline based peptidomimetic inhibitors of hepatitis C virus NS3 protease [1].
  • The mutagenic activities of eleven nitro derivatives and eleven N-methyl-nitro derivatives of indoline, indole, indazole and benzimidazole were investigated in Salmonella TA98 and TA100 [2].
  • Indapamide (Lozol), an indoline antihypertensive drug with diuretic and vasodilating activities, was evaluated in 195 patients with mild to moderate essential hypertension (sitting DBP between 95 and 110 mmHg) in a multicentre, randomised, double-blind, parallel-group design trial [3].
 

High impact information on indoline

  • Free radical-mediated aryl amination and its use in a convergent [3 + 2] strategy for enantioselective indoline alpha-amino acid synthesis [4].
  • 6-Chloro-5-methyl-1-[[2-[(2-methyl-3-pyridyl)oxy]-5-pyridyl]carbamoyl]- indoline (SB-242084): the first selective and brain penetrant 5-HT2C receptor antagonist [5].
  • Tetrazole 34 was identified as the most potent (AT1 IC50 = 18 nM) AT1 receptor antagonist in a structurally distinct series of compounds derived from N-alkylation of dihydroindole 25 [6].
  • Oral administration of YM348 induced penile erections and hypolocomotion in rats, being completely inhibited by a selective 5-HT(2C) receptor antagonist, SB242084 (6-chloro-5-methyl-1-[6-(2-methylpyridin-3-yloxy) pyridin-3-yl carbamoyl] indoline) [7].
  • These data also show that in both the hDHFR and pcDHFR ternary complexes with (1) the indoline ring is partially disordered, with two static conformations that differ between structures [8].
 

Biological context of indoline

 

Anatomical context of indoline

  • Indole- and indoline-type basic COX-1-selective competitive inhibitors, 5-amino-1-(3,5-dimethylbenzoyl)-1H-indole (1) and 5-amino-1-(3,5-dimethylphenyl)-2,3-dihydro-1H-indole (2), were found to possess anti-angiogenic activity estimated as a tube formation-inhibition using human umbilical vein endothelial cells (HUVECs) [13].
 

Associations of indoline with other chemical compounds

  • Despite similar anxiolytic potential, the 5-hydroxytryptamine 2C receptor antagonist SB-242084 [6-chloro-5-methyl-1-[2-(2-methylpyrid-3-yloxy)-pyrid-5-yl carbamoyl] indoline] and chlordiazepoxide produced differential effects on electroencephalogram power spectra [14].
  • Reduction of the nitro group followed by intramolecular amination with ketone and aldehyde and amidation with ester produced indoline and oxindole derivatives, respectively, in excellent yield [15].
  • In contrast, the novel and selective 5-HT2C receptor antagonist, SB-242084 (6-chloro-5-methyl-1-[6-(2-methylpyridin-3-yloxy) pyridin-3-yl carbamoyl] indoline) (10.0 mg/kg, i.p.), markedly increased dialysate levels of DA and NA without modifying those of 5-HT [16].
  • Total synthesis of indole and dihydroindole alkaloids. VI. The total synthesis of some monomeric vinca alkaloids: dl-vincadine, dl-vincaminoreine, dl-vincaminorine, dl-vincadifformine, dl-minovine and dl-vincaminoridine [17].
  • The indoline analogue (1) was crystallized as ternary complexes with NADPH and hDHFR (1.9 A resolution) and pcDHFR (2.3 A resolution), while the trimethoxy quinazoline analogue (2) was crystallized as a binary complex with hDHFR in two polymorphic rhombohedral R3 lattices: R3(1) to 1.8 A resolution and R3(2) to 2.0 A resolution [8].
 

Gene context of indoline

  • The effect on ACAT activity was related to the length of the alkyl chain at the 1-position of indoline [18].
  • Notably, indoline derivatives 6a and 11 were potent beta3 AR agonists (beta3 EC50 = 13 and 19 nM, respectively), which showed good selectivity over binding to and minimal activation of the beta1 and beta2 ARs [19].
  • Indoline and 1,2-benzisoxazole systems also provided potent 5-HT1F receptor agonists, and the 5-HT1A receptor selectivity of the indoline- and 1,2-benzisoxazole-based 5-HT1F receptor agonists could be improved with modification of the benzoyl moiety of the benzamides [20].
 

Analytical, diagnostic and therapeutic context of indoline

  • To this end, the epoxy-amide derivative of indoline 14 was stereoselectively prepared and, after treatment with DDQ, transformed into the corresponding N-indole epoxyamide 15 [21].
  • The enantiomers of the previously reported racemic 6-amino-3-(chloromethyl)-1-[(5,6,7-trimethoxyindol-2-yl)carbonyl] indoline (amino-seco-CI-TMI) were prepared via resolution of a precursor by chiral HPLC [22].
  • The metabolism of 14C-indapamide labeled in the indoline ring was determined after a single oral administration of a solution (4.99 mg, 90.47 microCi) to four fasted adult male volunteers [23].

References

  1. The design and enzyme-bound crystal structure of indoline based peptidomimetic inhibitors of hepatitis C virus NS3 protease. Ontoria, J.M., Di Marco, S., Conte, I., Di Francesco, M.E., Gardelli, C., Koch, U., Matassa, V.G., Poma, M., Steinkühler, C., Volpari, C., Harper, S. J. Med. Chem. (2004) [Pubmed]
  2. Structure-activity relationships of nitro and methyl-nitro derivatives of indoline, indole, indazole and benzimidazole in Salmonella typhimurium. Vance, W.A., Okamoto, H.S., Wang, Y.Y. Mutat. Res. (1986) [Pubmed]
  3. Lower dose diuretic therapy in the treatment of patients with mild to moderate hypertension. Hall, W.D., Weber, M.A., Ferdinand, K., Flamenbaum, W., Marbury, T., Jain, A.K., Weidler, D., Weiss, R., Herron, J., Codispoti, J. Journal of human hypertension. (1994) [Pubmed]
  4. Free radical-mediated aryl amination and its use in a convergent [3 + 2] strategy for enantioselective indoline alpha-amino acid synthesis. Viswanathan, R., Prabhakaran, E.N., Plotkin, M.A., Johnston, J.N. J. Am. Chem. Soc. (2003) [Pubmed]
  5. 6-Chloro-5-methyl-1-[[2-[(2-methyl-3-pyridyl)oxy]-5-pyridyl]carbamoyl]- indoline (SB-242084): the first selective and brain penetrant 5-HT2C receptor antagonist. Bromidge, S.M., Duckworth, M., Forbes, I.T., Ham, P., King, F.D., Thewlis, K.M., Blaney, F.E., Naylor, C.B., Blackburn, T.P., Kennett, G.A., Wood, M.D., Clarke, S.E. J. Med. Chem. (1997) [Pubmed]
  6. Non-peptide angiotensin II receptor antagonists. 1. Design, synthesis, and biological activity of N-substituted indoles and dihydroindoles. Dhanoa, D.S., Bagley, S.W., Chang, R.S., Lotti, V.J., Chen, T.B., Kivlighn, S.D., Zingaro, G.J., Siegl, P.K., Patchett, A.A., Greenlee, W.J. J. Med. Chem. (1993) [Pubmed]
  7. Pharmacological profile of YM348, a novel, potent and orally active 5-HT2C receptor agonist. Kimura, Y., Hatanaka, K., Naitou, Y., Maeno, K., Shimada, I., Koakutsu, A., Wanibuchi, F., Yamaguchi, T. Eur. J. Pharmacol. (2004) [Pubmed]
  8. Structure determination of tetrahydroquinazoline antifolates in complex with human and Pneumocystis carinii dihydrofolate reductase: correlations between enzyme selectivity and stereochemistry. Cody, V., Luft, J.R., Pangborn, W., Gangjee, A., Queener, S.F. Acta Crystallogr. D Biol. Crystallogr. (2004) [Pubmed]
  9. A novel class of inhibitors for human and rat steroid 5alpha-reductases: synthesis and biological evaluation of indoline and aniline derivatives. III. Igarashi, S., Inami, H., Hara, H., Koutoku, H., Oritani, H., Mase, T. Chem. Pharm. Bull. (2000) [Pubmed]
  10. Lead optimization of [(S)-gamma-(arylamino)prolyl]thiazolidine focused on gamma-substituent: Indoline compounds as potent DPP-IV inhibitors. Sakashita, H., Akahoshi, F., Yoshida, T., Kitajima, H., Hayashi, Y., Ishii, S., Takashina, Y., Tsutsumiuchi, R., Ono, S. Bioorg. Med. Chem. (2007) [Pubmed]
  11. Synthesis of 6H-pyrrolo[3',4':2,3][1,4]diazepino[6,7,1-hi]indole-8,10(7H,9H)-diones using 3-bromo-4-(indol-1-yl)maleimide scaffold. Lakatosh, S.A., Luzikov, Y.N., Preobrazhenskaya, M.N. Org. Biomol. Chem. (2003) [Pubmed]
  12. Multiple mutations at the active site of naphthalene dioxygenase affect regioselectivity and enantioselectivity. Yu, C.L., Parales, R.E., Gibson, D.T. J. Ind. Microbiol. Biotechnol. (2001) [Pubmed]
  13. Anti-angiogenic activity of basic-type, selective cyclooxygenase (COX)-1 inhibitors. Sano, H., Noguchi, T., Miyajima, A., Hashimoto, Y., Miyachi, H. Bioorg. Med. Chem. Lett. (2006) [Pubmed]
  14. Despite similar anxiolytic potential, the 5-hydroxytryptamine 2C receptor antagonist SB-242084 [6-chloro-5-methyl-1-[2-(2-methylpyrid-3-yloxy)-pyrid-5-yl carbamoyl] indoline] and chlordiazepoxide produced differential effects on electroencephalogram power spectra. Kantor, S., Jakus, R., Molnar, E., Gyongyosi, N., Toth, A., Detari, L., Bagdy, G. J. Pharmacol. Exp. Ther. (2005) [Pubmed]
  15. Polyhydroxylated Indolines and Oxindoles from C-Glycosides via Sequential Henry Reaction, Michael Addition, and Reductive Amination/Amidation. Zou, W., Wu, A.T., Bhasin, M., Sandbhor, M., Wu, S.H. J. Org. Chem. (2007) [Pubmed]
  16. Serotonin (5-HT)2C receptors tonically inhibit dopamine (DA) and noradrenaline (NA), but not 5-HT, release in the frontal cortex in vivo. Millan, M.J., Dekeyne, A., Gobert, A. Neuropharmacology (1998) [Pubmed]
  17. Total synthesis of indole and dihydroindole alkaloids. VI. The total synthesis of some monomeric vinca alkaloids: dl-vincadine, dl-vincaminoreine, dl-vincaminorine, dl-vincadifformine, dl-minovine and dl-vincaminoridine. Kutney, J.P., Chan, K.K., Failli, A., Fromson, J.M., Gletsos, C., Leutwiler, A., Nelson, V.R., de Souza, J.P. Helv. Chim. Acta (1975) [Pubmed]
  18. Bioavailable acyl-CoA: cholesterol acyltransferase inhibitor with anti-peroxidative activity: synthesis and biological activity of novel indolinyl amide and urea derivatives. Kamiya, S., Shirahase, H., Yoshimi, A., Nakamura, S., Kanda, M., Matsui, H., Kasai, M., Takahashi, K., Kurahashi, K. Chem. Pharm. Bull. (2000) [Pubmed]
  19. Human beta3 adrenergic receptor agonists containing cyanoguanidine and nitroethylenediamine moieties. Brockunier, L.L., Candelore, M.R., Cascieri, M.A., Liu, Y., Tota, L., Wyvratt, M.J., Fisher, M.H., Weber, A.E., Parmee, E.R. Bioorg. Med. Chem. Lett. (2001) [Pubmed]
  20. Design, synthesis and evaluation of bicyclic benzamides as novel 5-HT1F receptor agonists. Zhang, D., Kohlman, D., Krushinski, J., Liang, S., Ying, B.P., Reilly, J.E., Dinn, S.R., Wainscott, D.B., Nutter, S., Gough, W., Nelson, D.L., Schaus, J.M., Xu, Y.C. Bioorg. Med. Chem. Lett. (2004) [Pubmed]
  21. A convergent synthetic approach to the nucleoside-type liposidomycin antibiotics. Sarabia, F., Martín-Ortiz, L., López-Herrera, F.J. Org. Lett. (2003) [Pubmed]
  22. Cytotoxicity and DNA interaction of the enantiomers of 6-amino-3-(chloromethyl)-1-[(5,6,7-trimethoxyindol-2-yl)carbonyl]indo- line (amino-seco-CI-TMI). Tercel, M., Gieseg, M.A., Milbank, J.B., Boyd, M., Fan, J.Y., Tan, L.K., Wilson, W.R., Denny, W.A. Chem. Res. Toxicol. (1999) [Pubmed]
  23. The disposition of 14C-indapamide in man. Klunk, L.J., Ringel, S., Neiss, E.S. Journal of clinical pharmacology. (1983) [Pubmed]
 
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