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L-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid, also known as (S)-(-)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, is a quinoline derivative with the chemical formula C10H12NO2. It is a white to light yellow crystalline powder and is primarily used as an intermediate in the synthesis of quinapril, a medication developed by Pfizer for the treatment of hypertension, congestive heart failure, and angioedema.

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  • 74163-81-8 Structure
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    1. Product Name: L-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid
    2. Synonyms: (S)-TIC;(S)-N-tert-1,2,3,4-tetrahydroisoquinoline -3-carboxamide;L-1,2,3,4-Tetrahydro;4-Tetrahydro-3-Isoquinolinecarboxylic acid;[S]-1,2,3,4-Tetrahydro-3-Isoquinolingcarboxylic Acid;(S)-1, 2, 3, 4-tetrahydro-3-isoquinolinecarboxylic acid (for Quinapril);(3S)-1,2,3,4-TETRAHYDRO-3-ISOQUINOLINECA;(S)-1,2,3,4-Tetrahydro-3-isoquinoline-carboxylic acid hydrochloride, 95+%
    3. CAS NO:74163-81-8
    4. Molecular Formula: C10H11NO2
    5. Molecular Weight: 177.2
    6. EINECS: -0
    7. Product Categories: Quinolines, Isoquinolines & Quinoxalines;IsoquinolinesPeptide Synthesis;Chiral Building Blocks;Heterocyclic Building Blocks;Others;Unnatural Amino Acid Derivatives;Peptide Synthesis;a-amino;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Halogenated Heterocycles ,Thiophenes ,Thiazolines/Thiazolidines;Amino Acids;Carboxylic Acids;Quinolines, Isoquinolines & Quinoxalines;chiral;(intermediate of quinapril);Carboxylic Acids
    8. Mol File: 74163-81-8.mol
    9. Article Data: 35
  • Chemical Properties

    1. Melting Point: >300 °C(lit.)
    2. Boiling Point: 309.12°C (rough estimate)
    3. Flash Point: 178.8 °C
    4. Appearance: white to light yellow crystal powder
    5. Density: 1.1607 (rough estimate)
    6. Vapor Pressure: 5.62E-07mmHg at 25°C
    7. Refractive Index: -166 ° (C=1, 1mol/L NaOH)
    8. Storage Temp.: Store at 0-5°C
    9. Solubility: N/A
    10. PKA: 2.21±0.20(Predicted)
    11. BRN: 4842199
    12. CAS DataBase Reference: L-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid(CAS DataBase Reference)
    13. NIST Chemistry Reference: L-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid(74163-81-8)
    14. EPA Substance Registry System: L-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid(74163-81-8)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36/37/38
    3. Safety Statements: 26-36-37/39
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 74163-81-8(Hazardous Substances Data)

74163-81-8 Usage

Uses

Used in Pharmaceutical Industry:
L-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid is used as a key intermediate in the synthesis of quinapril for the treatment of various cardiovascular conditions. Its role in the production of quinapril is crucial, as quinapril is an angiotensin-converting enzyme (ACE) inhibitor that helps in regulating blood pressure and managing heart-related issues.
Used in Research and Development:
L-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid is also utilized in research and development for the discovery and development of new pharmaceutical compounds. Its unique chemical structure allows scientists to explore its potential in creating novel drugs with improved efficacy and reduced side effects.
Used in Quality Control and Standardization:
In the pharmaceutical industry, L-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid is employed in quality control processes to ensure the purity and potency of the final drug product. It is used as a reference compound for the standardization of quinapril and related medications, helping to maintain consistent quality and effectiveness across different batches and manufacturers.

Check Digit Verification of cas no

The CAS Registry Mumber 74163-81-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,4,1,6 and 3 respectively; the second part has 2 digits, 8 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 74163-81:
(7*7)+(6*4)+(5*1)+(4*6)+(3*3)+(2*8)+(1*1)=128
128 % 10 = 8
So 74163-81-8 is a valid CAS Registry Number.
InChI:InChI=1/C10H11NO2.ClH/c12-10(13)9-5-7-3-1-2-4-8(7)6-11-9;/h1-4,9,11H,5-6H2,(H,12,13);1H/t9-;/m0./s1

74163-81-8 Well-known Company Product Price

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  • TCI America

  • (T1515)  (S)-(-)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic Acid  >98.0%(T)

  • 74163-81-8

  • 5g

  • 550.00CNY

  • Detail
  • TCI America

  • (T1515)  (S)-(-)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic Acid  >98.0%(T)

  • 74163-81-8

  • 25g

  • 1,450.00CNY

  • Detail
  • Alfa Aesar

  • (L14422)  (S)-(-)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid, 97%   

  • 74163-81-8

  • 1g

  • 280.0CNY

  • Detail
  • Alfa Aesar

  • (L14422)  (S)-(-)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid, 97%   

  • 74163-81-8

  • 5g

  • 924.0CNY

  • Detail
  • Alfa Aesar

  • (L14422)  (S)-(-)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid, 97%   

  • 74163-81-8

  • 25g

  • 2976.0CNY

  • Detail
  • Aldrich

  • (421626)  (S)-1,2,3,4-Tetrahydro-3-isoquinolinecarboxylicacid  97%

  • 74163-81-8

  • 421626-5G

  • 636.48CNY

  • Detail

74163-81-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name (S)-(-)-1,2,3,4-Tetrahydroisoquinoline-3-Carboxylic Acid

1.2 Other means of identification

Product number -
Other names (3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:74163-81-8 SDS

74163-81-8Synthetic route

formaldehyd
50-00-0

formaldehyd

L-phenylalanine
63-91-2

L-phenylalanine

L-Tic-OH
74163-81-8

L-Tic-OH

Conditions
ConditionsYield
With hydrogenchloride In water at 90℃; for 12h; Pictet-Spengler Synthesis;98%
With hydrogenchloride In water at 90℃; for 12h;98%
With hydrogenchloride at 85℃; for 9h; Pictet-Spengler condensation;95%
(-)-menthyl (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate
143767-56-0

(-)-menthyl (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

L-Tic-OH
74163-81-8

L-Tic-OH

Conditions
ConditionsYield
With sodium hydroxide In methanol for 6h; Ambient temperature;94%
(S)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid, phenylmethylester
77497-96-2

(S)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid, phenylmethylester

L-Tic-OH
74163-81-8

L-Tic-OH

Conditions
ConditionsYield
With sodium hydroxide In water for 15h; Ambient temperature;81%
With hydrogen; palladium on activated charcoal In ethanol; water; acetic acid for 4h; Ambient temperature;75.4%
(10aS)-3,3-Bis(trifluoromethyl)-1-oxo-(1,2,3,4-tetrahydroisoquinolino)[2,3-c]oxazolidine
367952-43-0

(10aS)-3,3-Bis(trifluoromethyl)-1-oxo-(1,2,3,4-tetrahydroisoquinolino)[2,3-c]oxazolidine

L-Tic-OH
74163-81-8

L-Tic-OH

Conditions
ConditionsYield
With water In isopropyl alcohol at 20℃;72%
(R,S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
67123-97-1

(R,S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

L-Tic-OH
74163-81-8

L-Tic-OH

Conditions
ConditionsYield
With ammonium hydroxide; borane-ammonia complex; recombinant Escherichia coli BL21 (DE3) cells expressed D-amino acid oxidase from Fusarium solani M-0718 In water at 30℃; pH=8; Resolution of racemate; Enzymatic reaction; enantioselective reaction;68%
(3R,10bS)-3-tert-Butyl-2-methyl-2,3,6,10b-tetrahydro-5H-imidazo[5,1-a]isoquinolin-1-one
123053-49-6

(3R,10bS)-3-tert-Butyl-2-methyl-2,3,6,10b-tetrahydro-5H-imidazo[5,1-a]isoquinolin-1-one

L-Tic-OH
74163-81-8

L-Tic-OH

Conditions
ConditionsYield
With hydrogenchloride; Dowex 50-WX8; acetic acid In water; toluene at 103℃; for 126h;67%
(3'S,4R,5S)-1,5-dimethyl-4-phenyl-3-(1',2',3',4'-tetrahydro-3'-isoquinolinylcarbonyl)-2-imidazolidinone
307304-56-9

(3'S,4R,5S)-1,5-dimethyl-4-phenyl-3-(1',2',3',4'-tetrahydro-3'-isoquinolinylcarbonyl)-2-imidazolidinone

A

L-Tic-OH
74163-81-8

L-Tic-OH

B

(3R)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
103733-65-9

(3R)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

Conditions
ConditionsYield
With water for 12h; Hydrolysis; epimerization; Heating; Title compound not separated from byproducts.;
ethyl 1,2,3,4-tetrahydroisoquinoline-3-(S)-carboxylate
15912-55-7, 41234-43-9, 55857-63-1

ethyl 1,2,3,4-tetrahydroisoquinoline-3-(S)-carboxylate

L-Tic-OH
74163-81-8

L-Tic-OH

Conditions
ConditionsYield
With chicken liver acetone; water pH=7.5;
1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
57060-86-3

1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

L-Tic-OH
74163-81-8

L-Tic-OH

Conditions
ConditionsYield
With chicken liver acetone; water for 2h; pH=7.5;
(+/-)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid butyl ester

(+/-)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid butyl ester

L-Tic-OH
74163-81-8

L-Tic-OH

Conditions
ConditionsYield
With chicken liver acetone; water pH=7.5;
α,α'-dibromo-o-xylene
91-13-4

α,α'-dibromo-o-xylene

chiral Ni complex of Schiff base of glycine and BPB

chiral Ni complex of Schiff base of glycine and BPB

L-Tic-OH
74163-81-8

L-Tic-OH

Conditions
ConditionsYield
Stage #1: α,α'-dibromo-o-xylene; chiral Ni complex of Schiff base of glycine and BPB With sodium hydroxide In acetonitrile at 20℃; for 0.666667h;
Stage #2: In hydrogenchloride; methanol at 50℃; for 0.333333h;
Stage #3: In ammonium hydroxide
L-phenylalanine
63-91-2

L-phenylalanine

Gly-NH-Rink-resinEt halide

Gly-NH-Rink-resinEt halide

L-Tic-OH
74163-81-8

L-Tic-OH

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 91 percent / dimethylsulfoxide
2: 65 percent / SOCl2
3: BF3*OEt2 / 20 °C
4: 72 percent / H2O / propan-2-ol / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: 91 percent / dimethylsulfoxide
2: 82 percent / TFA / CHCl3 / 0.5 h
3: 72 percent / H2O / propan-2-ol / 20 °C
View Scheme
(4S)-4-Benzyl-2,2-bis(trifluoromethyl)-1,3-oxazolidin-5-one
150582-52-8

(4S)-4-Benzyl-2,2-bis(trifluoromethyl)-1,3-oxazolidin-5-one

L-Tic-OH
74163-81-8

L-Tic-OH

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 65 percent / SOCl2
2: BF3*OEt2 / 20 °C
3: 72 percent / H2O / propan-2-ol / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 82 percent / TFA / CHCl3 / 0.5 h
2: 72 percent / H2O / propan-2-ol / 20 °C
View Scheme
(4S)-4-Benzyl-2,2-bis(trifluoromethyl)-3-chloromethyl-1,3-oxazolidin-5-one
367952-46-3

(4S)-4-Benzyl-2,2-bis(trifluoromethyl)-3-chloromethyl-1,3-oxazolidin-5-one

L-Tic-OH
74163-81-8

L-Tic-OH

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: BF3*OEt2 / 20 °C
2: 72 percent / H2O / propan-2-ol / 20 °C
View Scheme
(+/-)-2-acetyl-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid
143767-54-8

(+/-)-2-acetyl-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid

L-Tic-OH
74163-81-8

L-Tic-OH

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 86 percent / 6 N aq. HCl / 4 h / Heating
2: 83 percent / p-TsOH*H2O / toluene / 30 h / Heating
3: 94 percent / NaOH / methanol / 6 h / Ambient temperature
View Scheme
o-Xylylene dichloride
612-12-4

o-Xylylene dichloride

L-Tic-OH
74163-81-8

L-Tic-OH

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: NaOMe / 4 h / Heating
2: 6 N aq. HCl / 4 h / Heating
3: 83 percent / p-TsOH*H2O / toluene / 30 h / Heating
4: 94 percent / NaOH / methanol / 6 h / Ambient temperature
View Scheme
Multi-step reaction with 5 steps
1: NaOMe / 4 h / Heating
2: 1.) KOH, 2.) 2 N HCl / 1.) MeOH, H2O, reflux, 4 h, 2.) EtOAc, pH 1
3: 86 percent / 6 N aq. HCl / 4 h / Heating
4: 83 percent / p-TsOH*H2O / toluene / 30 h / Heating
5: 94 percent / NaOH / methanol / 6 h / Ambient temperature
View Scheme
dimethyl 2-acetyl-1,2,3,4-tetrahydro-3,3-isoquinolinedicarboxylate
143767-55-9

dimethyl 2-acetyl-1,2,3,4-tetrahydro-3,3-isoquinolinedicarboxylate

L-Tic-OH
74163-81-8

L-Tic-OH

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 6 N aq. HCl / 4 h / Heating
2: 83 percent / p-TsOH*H2O / toluene / 30 h / Heating
3: 94 percent / NaOH / methanol / 6 h / Ambient temperature
View Scheme
Multi-step reaction with 4 steps
1: 1.) KOH, 2.) 2 N HCl / 1.) MeOH, H2O, reflux, 4 h, 2.) EtOAc, pH 1
2: 86 percent / 6 N aq. HCl / 4 h / Heating
3: 83 percent / p-TsOH*H2O / toluene / 30 h / Heating
4: 94 percent / NaOH / methanol / 6 h / Ambient temperature
View Scheme
α,α'-dibromo-o-xylene
91-13-4

α,α'-dibromo-o-xylene

sodium-compound of (+-)-acetylamino-cyano-acetic acid ethyl ester

sodium-compound of (+-)-acetylamino-cyano-acetic acid ethyl ester

L-Tic-OH
74163-81-8

L-Tic-OH

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 75 percent / NaOMe / 4 h / Heating
2: 6 N aq. HCl / 4 h / Heating
3: 83 percent / p-TsOH*H2O / toluene / 30 h / Heating
4: 94 percent / NaOH / methanol / 6 h / Ambient temperature
View Scheme
Multi-step reaction with 5 steps
1: 75 percent / NaOMe / 4 h / Heating
2: 1.) KOH, 2.) 2 N HCl / 1.) MeOH, H2O, reflux, 4 h, 2.) EtOAc, pH 1
3: 86 percent / 6 N aq. HCl / 4 h / Heating
4: 83 percent / p-TsOH*H2O / toluene / 30 h / Heating
5: 94 percent / NaOH / methanol / 6 h / Ambient temperature
View Scheme
Phenylalanine
150-30-1

Phenylalanine

α-ureido-β-phenyl-propionic acid

α-ureido-β-phenyl-propionic acid

L-Tic-OH
74163-81-8

L-Tic-OH

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 69 percent / conc. HCl
View Scheme
formaldehyd
50-00-0

formaldehyd

aqueous NH4OH

aqueous NH4OH

L-phenylalanine
63-91-2

L-phenylalanine

sulfuric acid
7664-93-9

sulfuric acid

L-Tic-OH
74163-81-8

L-Tic-OH

Conditions
ConditionsYield
In hydrogenchloride; ethanol; water
formaldehyd
50-00-0

formaldehyd

2-methyl-3-phenylpropionic acid
1009-67-2, 5628-72-8, 14367-54-5, 14367-67-0

2-methyl-3-phenylpropionic acid

L-Tic-OH
74163-81-8

L-Tic-OH

Conditions
ConditionsYield
With hydrogenchloride; water Reflux;
methanol
67-56-1

methanol

L-Tic-OH
74163-81-8

L-Tic-OH

methyl (3S)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylate
79815-19-3

methyl (3S)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylate

Conditions
ConditionsYield
With thionyl chloride100%
With thionyl chloride at 0 - 20℃;96%
With sulfuric acid for 12h; Reflux;95%
chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

L-Tic-OH
74163-81-8

L-Tic-OH

2-carboethoxy-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid
104882-53-3

2-carboethoxy-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid

Conditions
ConditionsYield
With sodium hydrogencarbonate In tetrahydrofuran; water 1.) 0 deg C to room temperature, 2.) room temperature, 3 h;100%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

L-Tic-OH
74163-81-8

L-Tic-OH

(3S)-2-tert-butoxycarbonyl-1,2,3,4-tetrahydroisoquinole-3-carboxylic acid
115962-35-1, 144069-68-1, 78879-20-6

(3S)-2-tert-butoxycarbonyl-1,2,3,4-tetrahydroisoquinole-3-carboxylic acid

Conditions
ConditionsYield
With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; for 144h;100%
With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; for 144h; Time;100%
With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; for 144h; Concentration;100%
methanol
67-56-1

methanol

L-Tic-OH
74163-81-8

L-Tic-OH

(S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, methyl ester, hydrochloride
78183-55-8

(S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, methyl ester, hydrochloride

Conditions
ConditionsYield
With thionyl chloride100%
With thionyl chloride at 0 - 40℃; for 21h; Inert atmosphere;99%
With thionyl chloride at 0 - 40℃; for 21h; Inert atmosphere;99%
With chloro-trimethyl-silane at 70℃; for 2h; Reflux;
L-Tic-OH
74163-81-8

L-Tic-OH

benzyl chloroformate
501-53-1

benzyl chloroformate

(S)-3,4-dihydro-1H-isoquinoline-2,3-dicarboxylic acid 2-benzyl ester
79261-58-8

(S)-3,4-dihydro-1H-isoquinoline-2,3-dicarboxylic acid 2-benzyl ester

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane; water at 20℃; for 16h;99%
With sodium hydroxide In 1,4-dioxane; water at 0 - 20℃; for 16.5h;99%
With sodium hydrogencarbonate In water at 20℃; for 1.5h;97%
L-Tic-OH
74163-81-8

L-Tic-OH

(S)-3-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline
18881-17-9, 62855-02-1, 62928-94-3, 63006-93-9

(S)-3-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
With dimethylsulfide borane complex; boron trifluoride diethyl etherate In tetrahydrofuran for 6h; Reduction; Heating;96%
With lithium aluminium tetrahydride In tetrahydrofuran for 6h; Heating;86%
With dimethylsulfide borane complex; boron trifluoride diethyl etherate In tetrahydrofuran78%
phosgene
75-44-5

phosgene

L-Tic-OH
74163-81-8

L-Tic-OH

(10aS)-10,10a-dihydro[1,3]oxazolo[3,4-b]isoquinoline-1,3,(5H)-dione
186606-17-7

(10aS)-10,10a-dihydro[1,3]oxazolo[3,4-b]isoquinoline-1,3,(5H)-dione

Conditions
ConditionsYield
In tetrahydrofuran; dichloromethane at -30 - 20℃;95%
L-Tic-OH
74163-81-8

L-Tic-OH

(S)-7-nitro-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
77141-07-2

(S)-7-nitro-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

Conditions
ConditionsYield
With sulfuric acid; nitric acid at -20℃; for 0.5h;93%
With sulfuric acid; nitric acid at -10℃; for 3.5h;90%
With sulfuric acid; potassium nitrate at 5 - 20℃;
formaldehyd
50-00-0

formaldehyd

L-Tic-OH
74163-81-8

L-Tic-OH

(S)-2-methyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

(S)-2-methyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

Conditions
ConditionsYield
With formic acid for 4h; Reflux;93%
formaldehyd
50-00-0

formaldehyd

L-Tic-OH
74163-81-8

L-Tic-OH

(S)-2-methyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrochloride

(S)-2-methyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrochloride

Conditions
ConditionsYield
Stage #1: formaldehyd; L-Tic-OH With formic acid In water for 4h; Reflux;
Stage #2: With hydrogenchloride In water Cooling with ice;
93%
ethanol
64-17-5

ethanol

L-Tic-OH
74163-81-8

L-Tic-OH

ethyl (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate
15912-55-7

ethyl (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

Conditions
ConditionsYield
With thionyl chloride Reflux;91%
With thionyl chloride
With sulfuric acid at 80℃; for 20h; Inert atmosphere;
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

benzaldehyde
100-52-7

benzaldehyde

L-Tic-OH
74163-81-8

L-Tic-OH

2-benzyl-1,2,3,4-tetrahydroisoquinoline-3-carbonitrile
1346425-09-9

2-benzyl-1,2,3,4-tetrahydroisoquinoline-3-carbonitrile

Conditions
ConditionsYield
In butan-1-ol at 200℃; for 0.166667h; decarboxylative Strecker reaction; Microwave irradiation; enantioselective reaction;91%
Fmoc-Leu-OH
35661-60-0

Fmoc-Leu-OH

Fmoc-Pro-OH
71989-31-6

Fmoc-Pro-OH

N-Fmoc L-Phe
35661-40-6

N-Fmoc L-Phe

Fmoc-Asn-OH
71989-16-7

Fmoc-Asn-OH

Fmoc-L-Arg-OH
91000-69-0

Fmoc-L-Arg-OH

L-Tic-OH
74163-81-8

L-Tic-OH

trifluoroacetic acid
76-05-1

trifluoroacetic acid

C46H69N15O8*C2HF3O2

C46H69N15O8*C2HF3O2

Conditions
ConditionsYield
Stage #1: Fmoc-Asn-OH With benzotriazol-1-ol; diisopropyl-carbodiimide In N,N-dimethyl-formamide for 2h;
Stage #2: With piperidine In N,N-dimethyl-formamide for 0.333333h;
Stage #3: Fmoc-Leu-OH; Fmoc-Pro-OH; N-Fmoc L-Phe; Fmoc-L-Arg-OH; L-Tic-OH; trifluoroacetic acid Further stages;
89%
bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]
12354-84-6, 12354-85-7

bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]

L-Tic-OH
74163-81-8

L-Tic-OH

chloro-pentamethylcyclopentadienyltetrahydroisoquinolinecarboxylato-iridium

chloro-pentamethylcyclopentadienyltetrahydroisoquinolinecarboxylato-iridium

Conditions
ConditionsYield
With CH3ONa In methanol; dichloromethane (Ar); addn. of a soln. of MeONa to a soln. of ligand in methanol, addn. to a soln. of iridium complex in CH2Cl2, stirring for 3 h; evapn., dissolving in CH2Cl2, filtration, concn., addn. of Et2O, filtration, washing with Et2O, pentane, drying in vac.; elem. anal.;85%
copper(II) acetate monohydrate
6046-93-1

copper(II) acetate monohydrate

L-Tic-OH
74163-81-8

L-Tic-OH

bis(tetrahydroisoquinolinecarboxylato)copper

bis(tetrahydroisoquinolinecarboxylato)copper

Conditions
ConditionsYield
In methanol (Ar); addn. of ligand to a soln. of copper salt in methanol; isolation, washing with methanol, ether, drying in vac.; elem. anal.;84%
L-Tic-OH
74163-81-8

L-Tic-OH

butan-1-ol
71-36-3

butan-1-ol

butyl (3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

butyl (3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

Conditions
ConditionsYield
With thionyl chloride at 120℃; for 16h; Inert atmosphere;84%
L-Tic-OH
74163-81-8

L-Tic-OH

N-(1-ethoxycarbonyl-3-phenylpropyl)-L-alanine
877932-98-4

N-(1-ethoxycarbonyl-3-phenylpropyl)-L-alanine

L-alanine acid chloride
129178-93-4

L-alanine acid chloride

quinapril
85441-61-8

quinapril

Conditions
ConditionsYield
With benzenesulfonamide; phosphorus pentachloride; triethylamine In n-heptane; dichloromethane; water83.9%
L-Tic-OH
74163-81-8

L-Tic-OH

isoquinoline-3-carboxylic acid
6624-49-3

isoquinoline-3-carboxylic acid

Conditions
ConditionsYield
With potassium permanganate In N,N-dimethyl-formamide at 0 - 20℃; for 100.5h; Inert atmosphere;83%
With potassium permanganate83%
With potassium permanganate In N,N-dimethyl-formamide at 20℃; for 72h; Cooling with ice;62%
palladium diacetate
3375-31-3

palladium diacetate

L-Tic-OH
74163-81-8

L-Tic-OH

bis(tetrahydroisoquinolinecarboxylato)palladium

bis(tetrahydroisoquinolinecarboxylato)palladium

Conditions
ConditionsYield
In methanol (Ar); addn. of ligand to a soln. of copper salt in methanol; isolation, washing with methanol, ether, drying in vac.; elem. anal.;81%
N-(tert-butyloxycarbonyl) azide
1070-19-5

N-(tert-butyloxycarbonyl) azide

L-Tic-OH
74163-81-8

L-Tic-OH

(3S)-2-tert-butoxycarbonyl-1,2,3,4-tetrahydroisoquinole-3-carboxylic acid
115962-35-1, 144069-68-1, 78879-20-6

(3S)-2-tert-butoxycarbonyl-1,2,3,4-tetrahydroisoquinole-3-carboxylic acid

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 48h; pH=10;80%
(Z)-9-octadecenoyl chloride
112-77-6

(Z)-9-octadecenoyl chloride

L-Tic-OH
74163-81-8

L-Tic-OH

(S)-2-oleoyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

(S)-2-oleoyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

Conditions
ConditionsYield
With potassium carbonate In water; acetone at 0 - 20℃;78%
tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

L-Tic-OH
74163-81-8

L-Tic-OH

1-oxo-1,3,4,9,9a,10-hexahydro-2-oxa-4a-aza-anthracene-4-carboxylic acid tert-butylamide

1-oxo-1,3,4,9,9a,10-hexahydro-2-oxa-4a-aza-anthracene-4-carboxylic acid tert-butylamide

Conditions
ConditionsYield
In 2,2,2-trifluoroethanol at -40 - 20℃; for 12h; Ugi reaction;77%
[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2
52462-29-0

[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2

L-Tic-OH
74163-81-8

L-Tic-OH

chloro-p-cymenetetrahydroisoquinolinecarboxylato-ruthenium

chloro-p-cymenetetrahydroisoquinolinecarboxylato-ruthenium

Conditions
ConditionsYield
With CH3ONa In methanol; dichloromethane (Ar); addn. of a soln. of MeONa to a soln. of ligand in methanol, addn. to a soln. of ruthenium complex in CH2Cl2, stirring for 3 h; evapn., dissolving in CH2Cl2, filtration through celite, concn., addn. to pentane, filtration, washing with pentane, drying in vac.; elem. anal.;77%
trans-di-μ-chloro-dichlorobis(triethylphosphine)diplatinum
15692-96-3

trans-di-μ-chloro-dichlorobis(triethylphosphine)diplatinum

L-Tic-OH
74163-81-8

L-Tic-OH

chloro-triethylphosphanetetrahydroisoquinolinecarboxylato-platinum

chloro-triethylphosphanetetrahydroisoquinolinecarboxylato-platinum

Conditions
ConditionsYield
With CH3ONa In methanol; dichloromethane (Ar); addn. of a soln. of MeONa to a soln. of ligand in methanol, addn. to a soln. of platinum complex in CH2Cl2, stirring for 3 h; evapn., dissolving in CH2Cl2, filtration, addn. of pentane, washing withpentane, drying in vac.; elem. anal.;77%
dichlorobis(triethylphosphine)-μ-dichlorodipalladium(II)

dichlorobis(triethylphosphine)-μ-dichlorodipalladium(II)

L-Tic-OH
74163-81-8

L-Tic-OH

chloro-triethylphosphanetetrahydroisoquinolinecarboxylato-palladium

chloro-triethylphosphanetetrahydroisoquinolinecarboxylato-palladium

Conditions
ConditionsYield
With CH3ONa In methanol; dichloromethane (Ar); addn. of a soln. of MeONa to a soln. of ligand in methanol, addn. to a soln. of palladium complex in CH2Cl2, stirring for 3 h; evapn., dissolving in CH2Cl2, filtration, evapn., addn. of pentane, cooling to -20°C, washing with pentane, drying in vac.; elem. anal.;76%
N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

L-Tic-OH
74163-81-8

L-Tic-OH

(S)-3,4-dihydro-1H-isoquinoline-2,3-dicarboxylic acid 2-benzyl ester
79261-58-8

(S)-3,4-dihydro-1H-isoquinoline-2,3-dicarboxylic acid 2-benzyl ester

Conditions
ConditionsYield
With sodium hydroxide In N,N-dimethyl-formamide at 0 - 20℃; for 27h;74.7%

74163-81-8Relevant articles and documents

NITROGEN-CONTAINING COMPOUND, METHOD FOR MANUFACTURING THE SAME, AND OPTICAL FUNCTIONAL MATERIAL INCLUDING THE SAME

-

Paragraph 0152-0153, (2021/08/21)

PROBLEM TO BE SOLVED: To provide a novel nitrogen-containing compound having luminescence property. SOLUTION: A nitrogen-containing compound represented by the following formula (I) in which RA, RB, R1, R2, R3, R4, and X are either one of the following (1) and (2). SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT

Novel isoquinoline-oxazoline chiral ligand and preparation and application thereof (by machine translation)

-

Paragraph 0021-0022; 0024, (2020/06/20)

The invention relates to a novel isoquinoline-oxazoline chiral ligand as well as preparation and application thereof. Substituted radicals R in the general formula1 And R2 The isoquinoline-oxazoline chiral ligand disclosed by the invention can be used as a ligand and a metal to form a complex or a composition for asymmetric catalysis, and particularly the asymmetric Michael addition of the isoquinoline-oxazoline ligand and the metal palladium can effectively catalyze the asymmetric Michael addition of boric acid and nitroolefin, and has excellent stereoselectivity. (by machine translation)

Chemoenzymatic Approach to (S)-1,2,3,4-Tetrahydroisoquinoline Carboxylic Acids Employing D-Amino Acid Oxidase

Ju, Shuyun,Qian, Mingxin,Xu, Gang,Yang, Lirong,Wu, Jianping

supporting information, p. 3191 - 3199 (2019/05/15)

Optically pure 1,2,3,4-tetrahydroisoquinoline carboxylic acids constitute an important class of building blocks for the synthesis of natural products and synthetic pharmaceuticals. However, redox deracemization of racemic 1,2,3,4-tetrahydroisoquinoline carboxylic acids as an attractive method is still challenging for the lack of suitable oxidoreductases. Herein, a D-amino acid oxidase from Fusarium solani M-0718 (FsDAAO) with broad substrate scope and excellent enantioselectivity was exploited through genome mining, and applied for the kinetic resolution of a number of racemic 1- and 3-carboxyl substituted tetrahydroisoquinolines to yield the corresponding (S)-enantiomers with excellent enantiomeric excess (ee) values (up to >99%). By using FsDAAO in combination with ammonia-borane in one pot, deracemization of these racemic carboxyl-substituted tetrahydroisoquinolines was achieved with conversions up to >98% and >99% ee. Preparative-scale deracemization of racemic 1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid and 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid was also demonstrated with good isolated yields (82% and 73%, respectively) and ee>99%. Our study provides an effective method for the synthesis of enantiomeric pure 1,2,3,4-tetrahydroisoquinoline carboxylic acids. This method is expected to provide access to chiral carboxyl-substituted 1,2,3,4-tetrahydroquinolines and 1,2,3,4-tetrahydro-?-carbolines. (Figure presented.).

Neuroligin-2-derived peptide-covered polyamidoamine-based (PAMAM) dendrimers enhance pancreatic β-cells' proliferation and functions

Munder, Anna,Moskovitz, Yoni,Meir, Aviv,Kahremany, Shirin,Levy, Laura,Kolitz-Domb, Michal,Cohen, Guy,Shtriker, Efrat,Viskind, Olga,Lellouche, Jean-Paul,Senderowitz, Hanoch,Chessler, Steven D.,Korshin, Edward E.,Ruthstein, Sharon,Gruzman, Arie

supporting information, p. 280 - 293 (2019/03/02)

Pancreatic β-cell membranes and presynaptic areas of neurons contain analogous protein complexes that control the secretion of bioactive molecules. These complexes include the neuroligins (NLs) and their binding partners, the neurexins (NXs). It has been recently reported that both insulin secretion and the proliferation rates of β-cells increase when cells are co-cultured with full-length NL-2 clusters. The pharmacological use of full-length protein is always problematic due to its unfavorable pharmacokinetic properties. Thus, NL-2-derived short peptide was conjugated to the surface of polyamidoamine-based (PAMAM) dendrimers. This nanoscale composite improved β-cell functions in terms of the rate of proliferation, glucose-stimulated insulin secretion (GSIS), and functional maturation. This functionalized dendrimer also protected β-cells under cellular stress conditions. In addition, various novel peptidomimetic scaffolds of NL-2-derived peptide were designed, synthesized, and conjugated to the surface of PAMAM in order to increase the biostability of the conjugates. However, after being covered by peptidomimetics, PAMAM dendrimers were inactive. Thus, the original peptide-based PAMAM dendrimer is a leading compound for continued research that might provide a unique starting point for designing an innovative class of antidiabetic therapeutics that possess a unique mode of action.

Multifunctional isoquinoline-oxazoline ligands of chemical and biological importance

Li, Wei,Wang, Guotong,Lai, Jixing,Li, Shengkun

supporting information, p. 5902 - 5905 (2019/05/27)

Multifunctional isoquinoline-oxazolines (MIQOXs) were conceived and synthesized from commercially available chiral amino acids. The multifunctional role of MIQOXs was demonstrated by Pd-catalyzed highly enantioselective addition of arylboronic acids to nitrostyrenes, and by the discovery of novel antifungal candidates.

Design and synthesis of nanoscaled IQCA-TAVV as a delivery system capable of antiplatelet activation, targeting arterial thrombus and releasing IQCA

Wu, Jianhui,Zhu, Haimei,Yang, Guodong,He, Jianhong,Wang, Yuji,Zhao, Shurui,Zhang, Xiaoyi,Gui, Lin,Zhao, Ming,Peng, Shiqi

, p. 1139 - 1158 (2018/03/09)

Background: Arterial thrombosis has been associated with a series of pathological conditions, and the discovery of arterial thrombosis inhibitor is of clinical importance. Methods: By analyzing the pharmacophores of anti-platelet agents, thrombus targeting peptide and anti-thrombotic nano-systems 3S-1,2,3,4-tetrahydroisoquino- line-3-carbonyl-Thr-Ala- Arg-Gly-Asp(Val)-Val (IQCA-TAVV) was designed and prepared as a nano-scaled arterial thrombosis inhibitor. Results: In vitro the nanoparticles of IQCA-TAVV were able to adhere onto the surface of activated platelets, attenuate activated platelets to extend pseudopodia and inhibit activated platelets to form aggregators. In vivo IQCA-TAVV targeted arterial thrombus, dose depend- ently inhibited arterial thrombosis with a 1 nmol/kg of minimal effective dose, and the activity was ~1670 folds of that of aspirin. Conclusion: IQCA-TAVV represented the design, preparation and application of nanomedicine capable of adhering on the surface of activated platelets, attenuating platelet activation, targeting arterial thrombus and inhibiting arterial thrombosis.

Stereoselective synthesis of 1,3-disubstituted dihydroisoquinolines vial-phenylalanine-derived dihydroisoquinoline N-oxides

Flores-Ferrándiz, Jesús,Carter, Nicholas,González-Soria, Maria José,Wasinska, Malgorzata,Gill, Daniel,Maciá, Beatriz,Caprio, Vittorio

supporting information, p. 6961 - 6968 (2018/10/17)

The preparation of chiral pool-derived nitrone 3 and its use in the protecting-group free, stereoselective synthesis of a range of 1,3-disubstituted tetrahydroisoquinolines is described. Grignard reagent additions to nitrone 3 yielded trans-1,3-disubstituted N-hydroxytetrahydroisoquinolines 6 with good levels of selectivity, while 1,3-dipolar cycloadditions to this nitrone provided access to 3-(2-hydroxyalkyl)isoquinolines 12 as single diastereomers.

Design and Discovery of Novel Chiral Antifungal Amides with 2-(2-Oxazolinyl)aniline as a Promising Pharmacophore

Zhang, Lu,Li, Wei,Xiao, Taifeng,Song, Zehua,Csuk, René,Li, Shengkun

, p. 8957 - 8965 (2018/09/10)

Inspired by established succinate dehydrogenase inhibitors (SDHIs), our continuing efforts toward the discovery of chiral antifungal amides turned to the optimization of their polar regions with 2-(2-oxazolinyl)aniline as a known pharmacophore. Scaffold hopping and bioactivity-guided convergent synthesis enabled the identification of promising antifungal categories. Fine tuning of the substituents and chirality furnished seven amides (1s, 1t, 2d, 2h, 2j, 3k, and 2l) as antifungal candidates, with EC50 values lower than 5 mg/L. The first investigation of chiral amides of acyclic acids as SDHIs was conducted, and compound 2d was selected as a promising candidate against Botrytis cinerea, with a preventative efficacy of up to 93.9% at 50 mg/L, which is better than that of boscalid. The different binding models between compounds with different configurations were simulated for compound 2d and its diastereoisomers. The benefits of synthetic accessibility and cost-effectiveness highlight the practical potential for compound 2d as a good alternative to known SDHI fungicides.

IQCA-TASS: a nano-scaled P-selectin inhibitor capable of targeting thrombus and releasing IQCA/TARGD(S)S in vivo

Wu, Jianhui,Zhu, Haimei,Zhao, Ming,Wang, Yuji,Yang, Guodong,Wang, Yaonan,Zhao, Shurui,Gui, Lin,Zhang, Xiaoyi,Peng, Shiqi

, p. 917 - 927 (2017/02/10)

Thrombosis is a serious threat to human health worldwide. Tetrahydroisoquinoline-3-carboxylic acid (IQCA) is an antithrombotic agent, while Thr-Ala-Arg-Gly-Asp(Ser)-Ser (TASS) can target thrombus. Herein, tetrahydro-isoquinoline-3-carbonyl-Thr-Ala-Arg-Gly-Asp(Ser)-Ser (IQCA-TASS) was designed with the aim towards the discovery of a nano-delivery system for targeting thrombus. In vitro, IQCA-TASS acted on P-selectin and down-regulated P-selectin expression. The IC50 values of IQCA-TASS against the platelet aggregation induced by four aggregators were less than 0.45 nM. In vivo, IQCA-TASS targeted thrombus, released IQCA and TASS inside the thrombus, showed dose-dependent anti-thrombotic action, of which the minimal effective dose was 1 nmol kg-1, and showed anti-inflammatory action. Even with the dose up to 1 μmol kg-1, a dose of 1000 times the minimal effective dose, IQCA-TASS still induced no toxic reaction. In rat plasma, IQCA-TASS formed nanoparticles with diameters of less than 41 nm. The interactions of the nanoparticles with both resting and activated platelets were imaged. IQCA-TASS should be a safe nano-medicine capable of targeting thrombus and releasing anti-thrombotic/anti-inflammatory pharmacophores in disease sites.

Environment-responsive multivalent isoquinoline-3-carboxylic acid conjugate, and preparation method and application thereof

-

Paragraph 0023; 0027; 0028, (2017/09/01)

The invention discloses an environment-responsive multivalent isoquinoline-3-carboxylic acid conjugate, and a preparation method and application thereof, belonging to the field of isoquinoline-3-carboxylic acid conjugates. According to the invention, 3,3'-dithiopropane diacid is used as a linking arm for coupling four isoquinoline-3-carboxylic acids with tris(2-aminoethyl)amine so as to form an isoquinoline derivative; multivalent synergism of a plurality of pharmacophores on a drug carrier is exerted on the lesion site of a tumor, so the antitumor activity of the antitumor drug is substantially improved; and through the environmental redox response of a disulfide bond to tumors, intelligent targeted release of the antitumor drug to a tumor part is realized, and toxicity of the antitumor drug to normal tissue is effectively reduced.

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