2-(1,2,3,4-TETRAHYDRO-ISOQUINOLIN-1-YLMETHYL)-ISOINDOLE-1,3-DIONE - CAS 310451-86-6
Category:
Main Product
Product Name:
2-(1,2,3,4-TETRAHYDRO-ISOQUINOLIN-1-YLMETHYL)-ISOINDOLE-1,3-DIONE
Catalog Number:
310451-86-6
Synonyms:
TIMTEC-BB SBB001749; 1-PHTHALIMIDOMETHYL-1,2,3,4-TETRAHYDROISOQUINOLINE; 2-(1,2,3,4-TETRAHYDRO-ISOQUINOLIN-1-YLMETHYL)-ISOINDOLE-1,3-DIONE
CAS Number:
310451-86-6
Molecular Weight:
292.33
Molecular Formula:
C18H16N2O2
COA:
Inquire
MSDS:
Inquire
Canonical SMILES:
C1CNC(C2=CC=CC=C21)CN3C(=O)C4=CC=CC=C4C3=O
InChI:
InChI=1S/C18H16N2O2/c21-17-14-7-3-4-8-15(14)18(22)20(17)11-16-13-6-2-1-5-12(13)9-10-19-16/h1-8,16,19H,9-11H2
InChIKey:
OOOHRYLFPGOMKQ-UHFFFAOYSA-N
Chemical Structure
CAS 310451-86-6 2-(1,2,3,4-TETRAHYDRO-ISOQUINOLIN-1-YLMETHYL)-ISOINDOLE-1,3-DIONE

Reference Reading


1.Thalidomide (5HPP-33) suppresses microtubule dynamics and depolymerizes the microtubule network by binding at the vinblastine binding site on tubulin.
Rashid A1, Kuppa A1, Kunwar A1, Panda D1. Biochemistry. 2015 Mar 31;54(12):2149-59. doi: 10.1021/bi501429j. Epub 2015 Mar 17.
Thalidomides were initially thought to be broad-range drugs specifically for curing insomnia and relieving morning sickness in pregnant women. However, its use was discontinued because of a major drawback of causing teratogenicity. In this study, we found that a thalidomide derivative, 5-hydroxy-2-(2,6-diisopropylphenyl)-1H-isoindole-1,3-dione (5HPP-33), inhibited the proliferation of MCF-7 with a half-maximal inhibitory concentration of 4.5 ± 0.4 μM. 5HPP-33 depolymerized microtubules and inhibited the reassembly of cold-depolymerized microtubules in MCF-7 cells. Using time-lapse imaging, the effect of 5HPP-33 on the dynamics of individual microtubules in live MCF-7 cells was analyzed. 5HPP-33 (5 μM) decreased the rates of growth and shortening excursions by 34 and 33%, respectively, and increased the time microtubules spent in the pause state by 92% as compared to that of the vehicle-treated MCF-7 cells. 5HPP-33 (5 μM) reduced the dynamicity of microtubules by 62% compared to the control.
2.2,2',2''-[(2,4,6-Trimeth-oxy-benzene-1,3,5-tri-yl)tris-(methyl-ene)]tris-(isoindole-1,3-dione).
Rosien JR1, Seichter W, Mazik M. Acta Crystallogr Sect E Struct Rep Online. 2013 Apr 10;69(Pt 5):o680. doi: 10.1107/S1600536813008428. Print 2013 May 1.
The title mol-ecule, C36H27N3O9, adopts an almost symmetric conformation in which the mean planes of the phthalimido units are inclined at dihedral angles of 81.1 (1), 85.3 (1) and 86.3 (1)° with respect to the plane of the central aromatic ring. The O atoms are involved in intra- and inter-molecular C-H⋯O hydrogen bonding. The crystal structure also features π-π arene inter-actions [minimum ring centroid separation = 3.683 (2) Å]. The present mode of non-covalent interactions leads to a three-dimensional supramolecular architecture.
3.Stress-induced anhedonia is associated with the activation of the inflammatory system in the rat brain: Restorative effect of pharmacological intervention.
Rossetti AC1, Papp M2, Gruca P3, Paladini MS4, Racagni G5, Riva MA6, Molteni R7. Pharmacol Res. 2016 Jan;103:1-12. doi: 10.1016/j.phrs.2015.10.022. Epub 2015 Nov 1.
Major depression is a complex disease that originates from the interaction between a genetic background of susceptibility and environmental factors such as stress. At molecular level, it is characterized by dysfunctions of multiple systems including neurotransmitters, hormones, signalling pathways, neurotrophic and neuroplastic molecules and - more recently - inflammatory mediators. Accordingly, in the present study we used the chronic mild stress (CMS) paradigm in the rat to elucidate to what extent brain inflammation may contribute to the development and/or the maintenance of an anhedonic phenotype and how pharmacological intervention may interfere with such behavioral and molecular stress-induced alterations. To this aim, adult male rats were exposed to CMS for 2 weeks and the cerebral expression of several mediators of the inflammatory system was evaluated in the hippocampus and prefrontal cortex of both stressed and control animals in parallel with the sucrose intake.
4.Synthesis, in vitro protoporphyrinogen oxidase inhibition, and herbicidal activity of N-(benzothiazol-5-yl)hexahydro-1H-isoindole-1,3-diones and N-(benzothiazol-5-yl)hexahydro-1H-isoindol-1-ones.
Wu QY1, Jiang LL, Zuo Y, Wang ZF, Xi Z, Yang GF. Chem Biol Drug Des. 2014 Oct;84(4):431-42. doi: 10.1111/cbdd.12331. Epub 2014 May 12.
Protoporphyrinogen oxidase (EC 1.3.3.4) is one of the most significant targets for a large family of herbicides. As part of our continuous efforts to search for novel protoporphyrinogen oxidase-inhibiting herbicides, N-(benzothiazol-5-yl)tetrahydroisoindole-1,3-dione was selected as a lead compound for structural optimization, leading to the syntheses of a series of novel N-(benzothiazol-5-yl)hexahydro-1H-isoindole-1,3-diones (1a-o) and N-(benzothiazol-5-yl)hexahydro-1H-isoindol-1-ones (2a-i). These newly prepared compounds were characterized by elemental analyses, (1) H NMR, and ESI-MS, and the structures of 1h and 2h were further confirmed by X-ray diffraction analyses. The bioassays indicated that some compounds displayed comparable or higher protoporphyrinogen oxidase inhibition activities in comparison with the commercial control. Very promising, compound 2a, ethyl 2-((6-fluoro-5-(4,5,6,7-tetrahydro-1-oxo-1H-isoindol-2(3H)-yl)benzo[d]thiazol-2-yl)-sulfanyl)acetate, was recognized as the most potent candidate with K(i) value of 0.