Category: 3308-94-9

Effect of N-alkylation on the affinities of analogs of spiperone for dopamine D₂ and serotonin 5-HT₂ receptors was written by Mach, Robert H.;Jackson, Joseph R.;Luedtke, Robert R.;Ivins, Kathryn J.;Molinoff, Perry B.;Ehrenkaufer, Richard L.. And the article was included in Journal of Medicinal Chemistry in 1992.Formula: C12H14ClFO2 This article mentions the following:

Two series of N-substituted spiperone analogs were prepared and evaluated in vitro to measure their affinities for dopamine D₂ and serotonin 5-HT₂ receptors. Substitution of the amide N with an alkyl group of 5 carbon units or less resulted in analogs displaying a low selectivity for D₂ compared to 5-HT₂ receptors. However, a moderate improvement in selectivity for D₂ receptors was observed with N-benzylspiperone. Substitution at either the ortho or para position of the benzyl group resulted in a further reduction in affinity for 5-HT₂ receptors and improvement in the selectivity ratio. Examination of N-substituted analogs of spiperone may provide insights into the topog. of the antagonist binding region of the 5-HT₂ receptor. The results also suggest that an ¹⁸F-labeled analog of N-(4-nitrobenzyl)spiperone may be a suitable tracer for studying D₂ receptors with positron emission tomog. since this compound displays a high selectivity for D₂ receptors relative to that of spiperone and N-methylspiperone. In the experiment, the researchers used many compounds, for example, 2-(3-Chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane (cas: 3308-94-9Formula: C12H14ClFO2).

2-(3-Chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane (cas: 3308-94-9) belongs to dioxole derivatives. Dioxoles, particularly fluorinated dioxoles, are used as co-monomers to make polymers that find use in forming protective coatings for chemical resistance. Dioxole functionalized metal-organic frameworks have also been recently reported.Formula: C12H14ClFO2

Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

Antagonism of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane stimulus with a newly identified 5-HT_2- versus 5-HT_1C-selective antagonist was written by Ismaiel, Abd M.;De Los Angeles, Joseph;Teitler, Milt;Ingher, Stacy;Glennon, Richard A.. And the article was included in Journal of Medicinal Chemistry in 1993.Synthetic Route of C12H14ClFO2 This article mentions the following:

DOM [i.e., 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane] is a 5-HT_1C/2 serotonin agonist that exerts stimulus control of behavior in animals. In order to determine if the discriminative stimulus effect of DOM is 5-HT_1C– or 5-HT₂-mediated, it would be informative to conduct tests of stimulus antagonism with a 5-HT_1C or 5-HT₂-selective antagonist. To date, no such agents exist. Although the neuroleptic agent spiperone binds at D2 dopamine receptors and 5-HT_1A serotonin receptors, (a) it displays about a 1000-fold selectivity for 5-HT₂ vs. 5-HT_1C sites and (b) it has been used as a “5-HT₂-selective” antagonist. Because spiperone is a behaviorally disruptive agent, it is not suitable for use in drug-discrimination studies. Using the spiperone mol. as a starting point, a limited structure-affinity investigation was conducted in order to identify a suitable antagonist with high affinity and selectivity for 5-HT₂ receptors, and yet an antagonist that might lack the disruptive actions of spiperone. Various modifications of the spiperone mol. were examined, but most resulted in decreased 5-HT₂ affinity or in loss of selectivity. One compound, 8-[3-(4-fluorophenoxy)propyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one (I), was shown to bind at 5-HT₂ sites with high affinity (K_i = 2 nM) and >2,000-fold selectivity vs. 5-HT_1C sites. In tests of stimulus antagonism using rats trained to discriminate 1 mg/kg of DOM from saline vehicle, I behaved as a potent antagonist (ED₅₀ = 0/003 mg/kg) and lacked the disruptive effects associated with spiperone. As such, (a) it would appear that the DOM stimulus is primarily a 5-HT₂-mediated, and not 5-HT_1C-mediated, phenomenon, and (b) compound I may find application in other pharmacol. investigations where spiperone may not be a suitable antagonist. In the experiment, the researchers used many compounds, for example, 2-(3-Chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane (cas: 3308-94-9Synthetic Route of C12H14ClFO2).

2-(3-Chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane (cas: 3308-94-9) belongs to dioxole derivatives. Dioxoles, particularly fluorinated dioxoles, are used as co-monomers to make polymers that find use in forming protective coatings for chemical resistance. Dioxole functionalized metal-organic frameworks have also been recently reported.Synthetic Route of C12H14ClFO2

Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

Heterocyclic spiro compounds: spiro[benzo[b]thiophene-4(5H),3′-pyrrolidines] was written by Stanetty, Peter;Froehlich, Hannes;Sauter, Fritz. And the article was included in Archiv der Pharmazie (Weinheim, Germany) in 1984.Electric Literature of C12H14ClFO2 This article mentions the following:

The title compounds were prepared and their ¹H and ¹³C NMR studied. Condensing benzothiophenone I (Z = O) with (NC)₂CH₂ gave dicyano compound I [Z = C(CN)₂] which was treated with NaCN and the product tricyano compound hydrolyzed and decarboxylated to give diacid II. Cyclization of II with RNH₂ [R = H, Me, (CH₂)₃NEt₂] gave the spiropyrrolidines III. III (R = H) and Cl(CH₂)_nNMe₂ (n = 2,3) gave III [R = (CH₂)_nNMe₂]. Reduction of III with LiAlH₄ gave IV. In the experiment, the researchers used many compounds, for example, 2-(3-Chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane (cas: 3308-94-9Electric Literature of C12H14ClFO2).

2-(3-Chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane (cas: 3308-94-9) belongs to dioxole derivatives. Dioxoles, particularly fluorinated dioxoles, are used as co-monomers to make polymers that find use in forming protective coatings for chemical resistance. Dioxole functionalized metal-organic frameworks have also been recently reported.Electric Literature of C12H14ClFO2

Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

New generation dopaminergic agents. 6. Structure-activity relationship studies of a series of 4-(aminoethoxy)indole and 4-(aminoethoxy)indolone derivatives based on the newly discovered 3-hydroxyphenoxyethylamine D₂ template was written by Mewshaw, Richard E.;Webb, Michael B.;Marquis, Karen L.;McGaughey, Georgia B.;Shi, Xiaojie;Wasik, Theodore;Scerni, Rosemary;Brennan, Julie A.;Andree, Terrance H.. And the article was included in Journal of Medicinal Chemistry in 1999.Related Products of 3308-94-9 This article mentions the following:

A series of 4-(aminoethoxy)indoles I [R₁ = CH₂Ph, (CH₂)₄Ph, n- Bu, etc.; R₂ = H, Me; NR₁R₂ = isoquinolino; X = H, Cl, Y = H, COCF₃, Cl] and a related series of 4-(aminoethoxy)indolones II [R₁ = Me, CH₂Ph, 2-naphthyl, etc.; R₂ = H, Me, (CH₂)₂, CH₂; X = H, Cl, F] were synthesized and evaluated for their affinity for both the high- and low-affinity agonist states (D₂^High and D₂^Low, resp.) of the dopamine (DA) D₂ receptor. The 4-aminoethoxy derivatives I and II were designed as bioisosteric analogs based on the phenol prototype 3-HOC₆H₄OCH₂CH₂NHCH₂Ph. The indolones II were observed to have high affinity for the D₂^High receptor. Comparison of their previously reported chroman analogs with the more flexible 4-(aminoethoxy)indoles revealed the chroman analogs to be more potent, whereas little loss in D₂^High affinity was observed when comparing the 4-(aminoethoxy)indolones with their resp. chroman analogs. Several regions of the phenoxyethylamine framework were modified and recognized as potential sites to modulate the level of intrinsic activity. A conformational anal. was performed and a putative bioactive conformation was proposed which fulfilled the D₂ agonist pharmacophore criteria based on the McDermed model. Structure-activity relationships gained from these studies have aided in the synthesis of D₂ partial agonists of varying intrinsic activity levels. These agents should be of therapeutic value in treating disorders resulting from hypo- and hyperdopaminergic activity, without the side effects associated with complete D₂ agonism or antagonism. In the experiment, the researchers used many compounds, for example, 2-(3-Chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane (cas: 3308-94-9Related Products of 3308-94-9).

2-(3-Chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane (cas: 3308-94-9) belongs to dioxole derivatives. Dioxoles, particularly fluorinated dioxoles, are used as co-monomers to make polymers that find use in forming protective coatings for chemical resistance. Dioxole functionalized metal-organic frameworks have also been recently reported.Related Products of 3308-94-9

Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

Conformationally restricted butyrophenones with mixed dopaminergic (D₂) and serotoninergic (5-HT_2A) affinities. Synthesis of 5-aminoethyl-and 6-aminomethyl-4-oxotetrahydroindoles as potential atypical antipsychotics was written by Masaguer, Christian F.;Casariego, Isabel;Ravina, Enrique. And the article was included in Chemical & Pharmaceutical Bulletin in 1999.Application In Synthesis of 2-(3-Chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane This article mentions the following:

5-Aminoethyl- and 6-aminomethyl-4-oxotetrahydroindoles were synthesized as butyrophenone derivatives in the indole series, as potential atypical antipsychotics. The affinities of these compounds for serotonin (5-HT_2A) and dopamine (D₂) receptors were evaluated in vitro. The ratios of pK_i‘s for 5-HT_2A/D₂ receptors may be useful for rapid screening of new compounds and assessing potential induction of extrapyramidal symptoms; ratio values ≥1.12 (Meltzer’s ratio) are predictive of an atypical antipsychotic profile. Two compounds, QF 0408B (I) and QF 0409B (II), showed high affinity for both D₂ and 5-HT_2A receptors, and their Meltzer’s ratios were 1.32 and 1.17 resp., while haloperidol showed a ratio of 0.93. In the experiment, the researchers used many compounds, for example, 2-(3-Chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane (cas: 3308-94-9Application In Synthesis of 2-(3-Chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane).

2-(3-Chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane (cas: 3308-94-9) belongs to dioxole derivatives. Dioxoles, particularly fluorinated dioxoles, are used as co-monomers to make polymers that find use in forming protective coatings for chemical resistance. Dioxole functionalized metal-organic frameworks have also been recently reported.Application In Synthesis of 2-(3-Chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane

Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

New generation dopaminergic agents. 6. Structure-activity relationship studies of a series of 4-(aminoethoxy)indole and 4-(aminoethoxy)indolone derivatives based on the newly discovered 3-hydroxyphenoxyethylamine D₂ template was written by Mewshaw, Richard E.;Webb, Michael B.;Marquis, Karen L.;McGaughey, Georgia B.;Shi, Xiaojie;Wasik, Theodore;Scerni, Rosemary;Brennan, Julie A.;Andree, Terrance H.. And the article was included in Journal of Medicinal Chemistry in 1999.Related Products of 3308-94-9 This article mentions the following:

A series of 4-(aminoethoxy)indoles I [R₁ = CH₂Ph, (CH₂)₄Ph, n- Bu, etc.; R₂ = H, Me; NR₁R₂ = isoquinolino; X = H, Cl, Y = H, COCF₃, Cl] and a related series of 4-(aminoethoxy)indolones II [R₁ = Me, CH₂Ph, 2-naphthyl, etc.; R₂ = H, Me, (CH₂)₂, CH₂; X = H, Cl, F] were synthesized and evaluated for their affinity for both the high- and low-affinity agonist states (D₂^High and D₂^Low, resp.) of the dopamine (DA) D₂ receptor. The 4-aminoethoxy derivatives I and II were designed as bioisosteric analogs based on the phenol prototype 3-HOC₆H₄OCH₂CH₂NHCH₂Ph. The indolones II were observed to have high affinity for the D₂^High receptor. Comparison of their previously reported chroman analogs with the more flexible 4-(aminoethoxy)indoles revealed the chroman analogs to be more potent, whereas little loss in D₂^High affinity was observed when comparing the 4-(aminoethoxy)indolones with their resp. chroman analogs. Several regions of the phenoxyethylamine framework were modified and recognized as potential sites to modulate the level of intrinsic activity. A conformational anal. was performed and a putative bioactive conformation was proposed which fulfilled the D₂ agonist pharmacophore criteria based on the McDermed model. Structure-activity relationships gained from these studies have aided in the synthesis of D₂ partial agonists of varying intrinsic activity levels. These agents should be of therapeutic value in treating disorders resulting from hypo- and hyperdopaminergic activity, without the side effects associated with complete D₂ agonism or antagonism. In the experiment, the researchers used many compounds, for example, 2-(3-Chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane (cas: 3308-94-9Related Products of 3308-94-9).

2-(3-Chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane (cas: 3308-94-9) belongs to dioxole derivatives. Dioxoles, particularly fluorinated dioxoles, are used as co-monomers to make polymers that find use in forming protective coatings for chemical resistance. Dioxole functionalized metal-organic frameworks have also been recently reported.Related Products of 3308-94-9

Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem