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N-[1-(4-hydroxy)butyl]indole-2-carboxamide is a chemical with a specific purpose. Lookchem provides you with multiple data and supplier information of this chemical.

600709-74-8

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600709-74-8 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 600709-74-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 6,0,0,7,0 and 9 respectively; the second part has 2 digits, 7 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 600709-74:
(8*6)+(7*0)+(6*0)+(5*7)+(4*0)+(3*9)+(2*7)+(1*4)=128
128 % 10 = 8
So 600709-74-8 is a valid CAS Registry Number.

600709-74-8Downstream Products

600709-74-8Relevant articles and documents

2-phenylcyclopropyl methylamine derivative, and preparation method and application thereof

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Paragraph 0405-0407, (2021/08/21)

The invention discloses a 2-phenylcyclopropyl methylamine derivative, and a preparation method and application thereof. The 2-phenylcyclopropyl methylamine derivative provided by the invention has a structure as shown in the following formula I, has affinity activity to a dopamine receptor and/or a 5-hydroxytryptamine receptor, and can be used for treating mental diseases.

Design and synthesis of bitopic 2-phenylcyclopropylmethylamine (pcpma) derivatives as selective dopamine d3 receptor ligands

Tan, Liang,Zhou, Qingtong,Yan, Wenzhong,Sun, Jian,Kozikowski, Alan P.,Zhao, Suwen,Huang, Xi-Ping,Cheng, Jianjun

, p. 4579 - 4602 (2020/06/08)

2-Phenylcyclopropylmethylamine (PCPMA) analogues have been reported as selective serotonin 2C agonists. On the basis of the same scaffold, we designed and synthesized a series of bitopic derivatives as dopamine D3R ligands. A number of these new compounds show a high binding affinity for D3R with excellent selectivity. Compound (1R,2R)-22e and its enantiomer (1S,2S)-22e show a comparable binding affinity for the D3R, but the former is a potent D3R agonist, while the latter acts as an antagonist. Molecular docking studies revealed different binding poses of the PCPMA moiety within the orthosteric binding pocket of the D3R, which might explain the different functional profiles of the enantiomers. Compound (1R,2R)-30q shows a high binding affinity for the D3R (Ki = 2.2 nM) along with good selectivity, as well as good bioavailability and brain penetration properties in mice. These results reveal that the PCPMA scaffold may serve as a privileged scaffold for the design of aminergic GPCR ligands.

Novel Bivalent Ligands Based on the Sumanirole Pharmacophore Reveal Dopamine D2 Receptor (D2R) Biased Agonism

Bonifazi, Alessandro,Yano, Hideaki,Ellenberger, Michael P.,Muller, Ludovic,Kumar, Vivek,Zou, Mu-Fa,Cai, Ning Sheng,Guerrero, Adrian M.,Woods, Amina S.,Shi, Lei,Newman, Amy Hauck

, p. 2890 - 2907 (2017/04/21)

The development of bivalent ligands has attracted interest as a way to potentially improve the selectivity and/or affinity for a specific receptor subtype. The ability to bind two distinct receptor binding sites simultaneously can allow the selective activation of specific G-protein dependent or β-arrestin-mediated cascade pathways. Herein, we developed an extended SAR study using sumanirole (1) as the primary pharmacophore. We found that substitutions in the N-1- and/or N-5-positions, physiochemical properties of those substituents, and secondary aromatic pharmacophores can enhance agonist efficacy for the cAMP inhibition mediated by Gi/o-proteins, while reducing or suppressing potency and efficacy toward β-arrestin recruitment. Compound 19 was identified as a new lead for its selective D2 G-protein biased agonism with an EC50 in the subnanomolar range. Structure-activity correlations were observed between substitutions in positions N-1 and/or N-5 of 1 and the capacity of the new bivalent compounds to selectively activate G-proteins versus β-arrestin recruitment in D2R-BRET functional assays.

Novel Analogues of (R)-5-(Methylamino)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one (Sumanirole) Provide Clues to Dopamine D2/D3 Receptor Agonist Selectivity

Zou, Mu-Fa,Keck, Thomas M.,Kumar, Vivek,Donthamsetti, Prashant,Michino, Mayako,Burzynski, Caitlin,Schweppe, Catherine,Bonifazi, Alessandro,Free, R. Benjamin,Sibley, David R.,Janowsky, Aaron,Shi, Lei,Javitch, Jonathan A.,Newman, Amy Hauck

, p. 2973 - 2988 (2016/05/19)

Novel 1-, 5-, and 8-substituted analogues of sumanirole (1), a dopamine D2/D3 receptor (D2R/D3R) agonist, were synthesized. Binding affinities at both D2R and D3R were higher when determined in competition with the agonist radioligand [3H]7-hydroxy-N,N-dipropyl-2-aminotetralin (7-OH-DPAT) than with the antagonist radioligand [3H]N-methylspiperone. Although 1 was confirmed as a D2R-preferential agonist, its selectivity in binding and functional studies was lower than previously reported. All analogues were determined to be D2R/D3R agonists in both GoBRET and mitogenesis functional assays. Loss of efficacy was detected for the N-1-substituted analogues at D3R. In contrast, the N-5-alkyl-substituted analogues, and notably the n-butyl-arylamides (22b and 22c), all showed improved affinity at D2R over 1 with neither a loss of efficacy nor an increase in selectivity. Computational modeling provided a structural basis for the D2R selectivity of 1, illustrating how subtle differences in the highly homologous orthosteric binding site (OBS) differentially affect D2R/D3R affinity and functional efficacy.

Novel Aryl Piperazine Derivatives With Medical Utility

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Page/Page column 31-32; 19, (2009/10/01)

This invention provides novel aryl piperazine derivatives having medical utility, in particular as modulators of dopamine and serotonin receptors, preferably the D3, D2-like and 5-HT2 receptor subtypes, and in particular u

Design, synthesis and biological evaluations of a novel series of enediynes constituted with DNA cleavage, alkylating and DNA binding agents via varies spacers

Linb, Chi-Fong,Hwanga, Martin,Kuo, Yao-Haur,Wu, Ming-Jung

, p. 525 - 532 (2008/02/11)

Among the three series of complicated combinatory enediynes, 3a-d were more active than 2a-c and 4a-b, in which 3a-b showed equally inhibitory activity against the growth of Hepa59T/VGH, KB and Hela with mean IC50 values lower than 10 μg/mL. Co

Design, synthesis, and biological evaluation of pyrrolo[2,1-c][1,4] benzodiazepine and indole conjugates as anticancer agents

Wang, Jeh-Jeng,Shen, Yu-Kai,Hu, Wan-Ping,Hsieh, Ming-Chu,Lin, Fu-Lung,Hsu, Ming-Kuan,Hsu, Mei-Hui

, p. 1442 - 1449 (2007/10/03)

A series of novel pyrrolo[2,1-c][1,4]benzodia/epine (PBD) hybrids linked with indole carboxylates is described. These compounds were prepared by linking C-8 of 3 (DC-81) with an indole 2-carbonyl moiety (9) through carbon chain linkers to afford PBD hybrid agents 17-21 in good yields. Preliminary in vivo tests show that these hybrid agents have potent antitumor activity. The cytotoxic studies of the hybrid agents on human melanoma A2058 cells indicate most of the hybrids induced higher cytotoxicity, better DNA-binding ability, an increase in the apoptotic sub-G1 population, and a significant reduction in ΔΨmt relative to compound 3. In addition, DNA flow cytometric analysis shows that hybrids actively induce a marked loss of cells from the G2/M phase of the cell cycle, which progresses to early apoptosis as detected by flow cytometry after double-staining with annexin V and propidium iodide (PI). Thus, we suggest that the hybrid agents are potent inducers of cell apoptosis in A2058 cells.

Novel pyrrolo[2,1-c][1,4] benzodiazepine-indole derivatives, their preparation process, and uses of the same

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Page 7-9, (2008/06/13)

Disclosed herein are novel pyrrolo[2,1-c][1,4]benzodiazepine-indole derivatives of formula (I): wherein each of the substituents is given the definition as set forth in the Specification and claims. Also disclosed are the preparation process of these derivatives and their uses in the manufacture of pharmaceutical compositions.

Synthesis and pharmacological evaluation of potent and highly selective D3 receptor ligands: Inhibition of cocaine-seeking behavior and the role of dopamine D3/D2 receptors

Campiani, Giuseppe,Butini, Stefania,Trotta, Francesco,Fattorusso, Caterina,Catalanotti, Bruno,Aiello, Francesca,Gemma, Sandra,Nacci, Vito,Novellino, Ettore,Stark, Jennifer Ann,Cagnotto, Alfredo,Fumagalli, Elena,Carnovali, Francesco,Cervo, Luigi,Mennini, Tiziana

, p. 3822 - 3839 (2007/10/03)

The synthesis, pharmacological evaluation, and structure - activity relationships (SARs) of a series of novel arylalkylpiperazines structurally related to BP897 (3) are described. In binding studies, the new derivatives were tested against a panel of dopamine, serotonin, and noradrenaline receptor subtypes. Focusing mainly on dopamine D3 receptors, SAR studies brought to light a number of structural features required for high receptor affinity and selectivity. Several heteroaromatic systems were explored for their dopamine receptor affinities, and combinations of synthesis, biology, and molecular modeling, were used to identify novel structural leads for the development of potent and selective D3 receptor ligands. Introduction of an indole ring linked to a dichlorophenylpiperazine system provided two of the most potent and selective ligands known to date (D 3 receptor affinity in the picomolar range). The intrinsic pharmacological properties of a subset of potent D3 receptor ligands were also assessed in [35S]-GTPγS binding assays. Evidence from animal studies, in particular, has highlighted the dopaminergic system's role in how environmental stimuli induce drug-seeking behavior. We therefore tested two novel D3 receptor partial agonists and a potent D 3-selective antagonist in vivo for their effect in the cocaine-seeking behavior induced by reintroduction of cocaine-associated stimuli after a long period of abstinence, and without any further cocaine. Compound 5g, a nonselective partial D3 receptor agonist with a pharmacological profile similar to 3, and 5p, a potent and selective D 3 antagonist, reduced the number of active lever presses induced by reintroduction of cocaine-associated stimuli. However, 5q, a highly potent and selective D3 partial agonist, did not have any effect on cocaine-seeking behavior. Although brain uptake studies are needed to establish whether the compounds achieve brain concentrations comparable to those active in vitro on the D3 receptor, our experiments suggest that antagonism at D2 receptors might significantly contribute to the reduction of cocaine craving by partial D3 agonists.

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