From Wikipedia, the free encyclopedia
Cysmethynil
Names
Preferred IUPAC name
2-[5-(3-Methylphenyl)-1-octyl-1H -indol-3-yl]acetamide
Other names
Cysmethynil, 2-(1-octyl-5-m -tolyl-1H -indol-3-yl)acetamide, 9J20
Identifiers
ChemSpider
UNII
InChI=1S/C25H32N2O/c1-3-4-5-6-7-8-14-27-18-22(17-25(26)28)23-16-21(12-13-24(23)27)20-11-9-10-19(2)15-20/h9-13,15-16,18H,3-8,14,17H2,1-2H3,(H2,26,28)
Y Key: QIXBOOVPFRZHQQ-UHFFFAOYSA-N
Y
O=C(N)Cc2c1cc(ccc1n(c2)CCCCCCCC)c3cccc(c3)C
Properties
C 25 H 32 N 2 O
Molar mass
−1
Density
1.068 g/cm3
Melting point
247.08 °C (476.74 °F; 520.23 K)
Boiling point
594.156 °C (1,101.481 °F; 867.306 K) at 760 mmHg
0.005429 mg/L
Vapor pressure
1.37×10−12 mmHg at 25 °C
Hazards
Flash point
313.134 °C (595.641 °F; 586.284 K)
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Cysmethynil is a chemical compound that is reported to inhibit Icmt , a protein that methylates a Ras protein , which then triggers uncontrolled cell growth. If Icmt no longer activates Ras, cell growth and proliferatation remains under normal control. As such, this small molecule has been investigated as a treatment for cancer. In animal models containing multiple human tumor growths, treatment with cysmethynil causes autophagy in the cell and results in cell death and reduced tumor burden. In prostate cancer cells, cysmethynil inhibits Icmt such that the cell is stuck in the G1 phase , and this leads to the autophagic cell death.[ 1] [ 2] [ 3] [ 4] [ 5]
^ Cysmethynil : A New Anti-Cancer Compound That Blocks the Icmt Protein Activation. Proceedings of the National Academy of Sciences, 28 Mar. 2005. Web. 19 Oct. 2012 ^ Arresting Prostate Cancer." The Journal of Biological Chemistry. American Society for Biochemistry and Molecular Biology, n.d. Web. 19 Oct. 2012 ^ New Compound Blocks Growth of Cancer Cells." Inside- Duke University Medical Center and Health System. N.p., 04 Apr. 2005. Web. 20 Oct. 2012 ^ Yang WS, Yeo SG, Yang S, Kim KH, Yoo BC, Cho JY. Isoprenyl carboxyl methyltransferase inhibitors: a brief review including recent patents. Amino Acids . 2017 Sep;49(9):1469-1485. doi :10.1007/s00726-017-2454-x PMID 28631011
^ Arendt KAM, Ntaliarda G, Armenis V, Kati D, Henning C, Giotopoulou GA, Pepe MAA, Klotz LV, Lamort AS, Hatz RA, Kobold S, Schamberger AC, Stathopoulos GT. An In Vivo Inflammatory Loop Potentiates KRAS Blockade. Biomedicines . 2022 Mar 3;10(3):592. doi :10.3390/biomedicines10030592 PMID 35327394
Tryptamines 4-Hydroxytryptamines esters /ethers 5-Hydroxy- and5-methoxytryptamines
2-Methyl-5-HT 4-HO-5-MeO-T 4-F-5-MeO-DMT 4,5-DHP-DMT 4,5-DHT 4,5-MDO-DMT 4,5-MDO-DiPT 5-BT 5-Ethoxy-DMT 5-HO-DET 5-HO-DiPT 5-HO-NiPT 5-HO-DPT 5-HTP (oxitriptan )5-MeO-2-TMT 5-MeO-34MPEMT 5-MeO-7,N ,N -TMT 5-MeO-DALT 5-MeO-DBT 5-MeO-DET 5-MeO-DiPT 5-MeO-DMT (N ,N ,O -TMS; O -methylbufotenine) 5-MeO-DPT 5-MeO-EiPT 5-MeO-EPT 5-MeO-MALT 5-MeO-MET 5-MeO-MiPT 5-MeO-NET 5-MeO-NiPT 5-MeO-NMT (O ,N -DMS) 5-MeO-PiPT 5-MeO-NBpBrT 5-MeO-T (5-MT; mexamine; O -methylserotonin) 5-MeO-T-NBOMe 5-MT-NB3OMe 5-NOT 5,6-DHT 5,6-MDO-DiPT 5,6-MDO-DMT 5,6-MDO-MiPT 5,6-MeO-MiPT 5,7-DHT Arachidonoyl serotonin ASR-3001 (5-MeO-iPALT) BAB Benanserin (BAS; SQ-4788) BGC20-761 Bufotenidine (5-HTQ; N ,N ,N -TMS) Bufotenin (5-HO-DMT; N ,N -DMS; mappine) Bufoviridine (5-SO-DMT) CP-132,484 Cqd 280 Cqd 285 Cqdd 280 EMDT (2-Et-5-MeO-DMT) HIOC Indorenate (TR-3369) Isamide (N -CA-5-MT) L-741604 MS-245 N -DEAOP-5-MeO-NETN -DEAOP-5-MeO-NMTN -Feruloylserotonin (moschamine)Norbufotenin (5-HO-NMT; NMS) O -Acetylbufotenine (5-AcO-DMT)O -Pivalylbufotenine (5-(t -BuCO)-DMT)Psilomethoxin (4-HO-5-MeO-DMT) Psilomethoxybin (4-PO-5-MeO-DMT) Serotonin (5-HT) N -Acetyltryptaminesα-Alkyltryptamines
5-Hydroxy- and 5-alkoxy-α-alkyltryptamines: 1-Pr-5-MeO-AMT 5-Allyloxy-AMT 5-Ethoxy-αMT 5-iPrO-αMT 5-MeO-αET 5-MeO-αMT (α,O -DMS; Alpha-O) α-Methyl-5-HTP α-Methylmelatonin α-Methylserotonin (5-HO-αMT; α-Me-5-HT) α,N ,O -TMS (5-MeO-α,N -DMT) α,N ,N ,O -TeMS (5-MeO-α,N ,N -TMT) AL-37350A (4,5-DHP-αMT) BW-723C86 Triptans Cyclized tryptamines
Barettin Bufothionine Ciclindole Cyclic 3-OHM Ergolines and lysergamides (e.g., LSD )Flucindole Frovatriptan Harmala alkaloidsβ-carbolines (e.g., 5-methoxyharmalan , 6-MeO-THH , 6-methoxyharmalan , 9-Me-BC , β-carboline (norharman) , fenharmane , harmaline , harmalol , harmane , harmine , pinoline , tetrahydroharmine , tryptoline )Iboga alkaloidsibogaine , ibogamine , noribogaine , tabernanthine )Ibogalogs (e.g., fluorogainalog , ibogainalog , ibogaminalog (DM-506) , LS-22925 , noribogainalog , noribogaminalog , PNU-22394 , tabernanthalog )Imidazolylindoles (e.g., AGH-107 , AGH-192 , AH-494 )LY-266,097 LY-344864 Metralindole O -MethylnordehydrobufoteninePartial ergolines and lysergamides (e.g., NDTDI , RU-27849 , RU-28251 , RU-28306 , FHATHBIN , LY-178210 , Bay R 1531 (LY-197206) , LY-293284 , 10,11-seco-LSD , 10,11-secoergoline (α,N -Pip-T) , CT-5252 )Pertines (e.g., alpertine , milipertine , oxypertine , solypertine )PHA-57378 Piperidinylethylindoles (e.g., Pip-T , indolylethylfentanyl )Pyrrolidinylethylindoles (e.g., Pyr-T , 4-HO-pyr-T , 5-MeO-pyr-T , 4-F-5-MeO-pyr-T )Pyrrolidinylmethylindoles (e.g., MPMI , 4-HO-MPMI (lucigenol) , 5F-MPMI , 5-MeO-MPMI , CP-135807 , eletriptan )Tetrahydropyridinylindoles (e.g., RS134-49 , RU-28253 )Yohimbans (e.g., yohimbine , rauwolscine , spegatrine , corynanthine , ajmalicine , reserpine , deserpidine , rescinnamine ) Isotryptamines Related compounds
2-Azapsilocin 4-Aza-5-MeO-DPT 5-Aza-4-MeO-DiPT 5-HIAA 5-HIAL 5-HITCA 5-MIAL 7-Aza-5-MeO-DiPT Amedalin Benzindopyrine Benzofurans (e.g., 3-APB , 5-MeO-DiBF , BPAP , 3-F-BPAP , dimemebfe , mebfap )Benzothiophenes (e.g., 3-APBT )CP-94253 CT-4436 Daledalin Gramine Histamine I-32 IAL IN-399 Indazoles (e.g., AL-34662 , AL-38022A , O -methyl-AL-34662VU6067416 , YM-348 )Indenes (e.g., C-DMT )Indolizines (e.g., TACT908 (2ZEDMA) , 1ZP2MA , 1Z2MAP1O )Indolylaminopropanes (e.g., 1-API , 2-API , 4-API , 5-API (5-IT; PAL-571) , 6-API (6-IT) , 7-API )Iprindole Latrepirdine Masupirdine Medmain Molindone Non-tryptamine triptans (e.g., avitriptan , LY-334370 , naratriptan )
Phenethylamines (e.g., phenethylamine , amphetamine )Piperidinylindoles (e.g., BRL-54443 , LY-334370 , naratriptan , sertindole , SN-22 )Pirlindole Pyridinylindoles (e.g., tepirindole )Pyrrolylethylamines (e.g., 2-pyrrolylethylamine (NEA) , 3-pyrrolylethylamine (3-NEA) , 3-pyrrolylpropylamine )Quinolinylethylamines (e.g., mefloquine )(R )-69 (3IQ) Ro60-0213 Selisistat Tetrahydropyridinylindoles (e.g., EMD-386088 , LY-367265 , RU-24,969 )Tetrindole Tiflucarbine Tipindole Zilpaterol (RU-42173)
