67123-97-1

Usage

Uses

Used in Organic Synthesis:
H-DL-TIC-OH is used as a building block in organic synthesis for the preparation of various pharmaceuticals, agrochemicals, and other organic compounds. Its unique structure and functional groups make it a versatile intermediate for the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
H-DL-TIC-OH is used as a key intermediate in the synthesis of various pharmaceutical compounds, including drugs for the treatment of neurological disorders, pain management, and other therapeutic applications. Its ability to form stable derivatives and participate in various chemical reactions makes it a valuable component in the development of new drugs.
Used in Agrochemical Industry:
H-DL-TIC-OH is used as a starting material in the synthesis of agrochemicals, such as pesticides and herbicides. Its reactivity and structural features enable the development of effective and targeted agrochemicals for crop protection and management.

InChI:InChI=1/C10H11NO2/c12-10(13)9-5-7-3-1-2-4-8(7)6-11-9/h1-4,9,11H,5-6H2,(H,12,13)

Upstream product

• 50-00-0 formaldehyd 
• 150-30-1 Phenylalanine 
• 109-87-5 Dimethoxymethane 
• 63-91-2 L-phenylalanine 
• 6624-49-3 isoquinoline-3-carboxylic acid 
• 143767-54-8 (R,S)-2-acetyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid 
• 143767-55-9 dimethyl 2-acetyl-1,2,3,4-tetrahydroisoquinoline-3,3-dicarboxylate 
• 612-12-4 o-Xylylene dichloride 
• 91-13-4 α,α'-dibromo-o-xylene 
• 673-06-3 D-(R)-phenylalanine 
• 76884-33-8 3-chloromethylisoquinoline hydrochloride 
• 90-41-5 2-phenylaniline 
• 159596-06-2 (-)menthyl D-1,2,3,4-tetrahydroisoquinoline-3-carboxylate 

Downstream Products

• 7661-41-8 3-Butyryl-isochinolin 
• 2744-08-3 decahydroisoquinoline 
• 82717-30-4 (+/-)-(4ar,8ac)-decahydro-isoquinoline-3ξ-carboxylic acid 
• 119751-71-2 2,3,3aα,4β,6,11,11aα,11bα-octahydro-2-methyl-4-(2-phenylethenyl)-1H-pyrrolo<3',4':3,4>pyrrolo<1,2-b>isoquinoline-1,3-dione 
• 119751-71-2 2,3,3aα,4α,6,11,11aα,11bα-octahydro-2-methyl-4-(2-phenylethenyl)-1H-pyrrolo<3',4':3,4>pyrrolo<1,2-b>isoquinoline-1,3-dione 
• 119751-71-2 2,3,3aα,4aβ,6,11,11aβ,11bα-octahydro-2-methyl-4-(2-phenylethenyl)-1H-pyrrolo<3',4':3,4>pyrrolo<1,2-b>isoquinoline-1,3-dione 
• 111157-55-2 2,3,3aα,,4β,6,11,11aα,11bα-octahydro-2-methyl-4-phenyl-1H-pyrrolo<3',4':3,4>pyrrolo<1,2-b>isoquinoline-1,3-dione 
• 111157-55-2 2,3,3aα,,4α,6,11,11aβ,11bα-octahydro-2-methyl-4-phenyl-1H-pyrrolo<3',4':3,4>pyrrolo<1,2-b>isoquinoline-1,3-dione 
• 57060-86-3 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid 
• 57060-88-5 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid,methyl ester hydrochloride 
• 143767-56-0 (-)-menthyl (R,S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate 
• 74618-46-5 dimethyl 4,9-dihydro-1-methylpyrrolo<1,2-b>isoquinoline-2,3-dicarboxylate 
• 82716-88-9 N-benzyloxycarbonyl-1,2,3,4-tetrahydro-3(S)-isoquinolinecarboxylic acid 
• 119-65-3 isoquinoline 

Relevant academic research and scientific papers

Discovery of pyridine tetrahydroisoquinoline thiohydantoin derivatives with low blood-brain barrier penetration as the androgen receptor antagonists

Prostate cancer (PC) is the most diagnosed type of malignancy in men and the major frequently cause of cancer-related death worldwide. The androgen receptor (AR) has become a promising drug target for the treatment of PC. Here, we reported the design, optimization and evaluation of pyridine tetrahydroisoquinoline thiohydantoin derivatives with improved activity and safety as potent AR antagonists. The most promising compound 42f exhibited potent inhibitory activity on AR and strongly blocked AR nuclear translocation. Moreover, 42f displayed promising in vitro antitumor activity toward AR-dependent prostate cancer cell lines (LNCaP) and also demonstrated therapeutic effects in LNCaP xenograft tumor model in mice (TGI: 79%) with no apparent toxicity observed in vivo. More importantly, 42f showed negligible penetration of the brain-blood barrier (BBB) compared with enzalutamide. These results provide a foundation for the development of a new class of androgen receptor antagonists for potential therapeutics against PC with lower seizurogenic risk for patients.

Exploring the tetrahydroisoquinoline thiohydantoin scaffold blockade the androgen receptor as potent anti-prostate cancer agents

Prostate cancer (PC) is a major cause of cancer-related male death in worldwide and the identification of new and improved potent anti-PC molecules is constantly required. A novel scaffold of tetrahydroisoquinoline thiohydantoin was rationally designed based on the enzalutamide structures and our pre-work, leading to the discovery of a series of new antiproliferative compounds. Several new analogues displayed improved androgen receptor (AR) antagonistic activity, while maintaining the higher selective toxicity toward LNCaP cells (AR-rich) versus DU145 cells (AR-deficient) compared to enzalutamide. In fact, compound 55 exhibited promising in vitro antitumor activity by impairing AR unclear translocation. More importantly, 55 showed better pharmacokinetic properties compared to the compound 1 reported in our pre-work. These results demonstrate a step towards the development of novel and improved AR antagonists.

Gene delivery system

The invention discloses a preparation method of a gene nano-liposome carrier Isoquinoline-3-acyl-RGDV(IRV) and an IRV/STAT3-siRNA gene delivery system. The IRV/STAT3-siRNA gene delivery system is composed of liposome carriers IRV and STAT3-siRNA, protamine and calf thymus DNA in a proportion, and has slow release and targeting effects. The cell transfection efficiency, the in-vitro anti-tumor activity, and the gene silencing efficiency and a cell action mechanism on the mRNA level and the protein level of a compound are evaluated with the lung cancer A549 cell strain as a model, and the result shows the IRV/STAT3-siRNA gene delivery system has more excellent anti-tumor activity and gene silencing efficiency compared with control groups. According to the system, the anti-tumor activity of the IRV/STAT3-siRNA gene delivery system is evaluated with an S180 ascites tumor mouse as a model, and the result shows that a 100% IRV/STAT3-siRNA group has an anti-tumor effect.

Immunomodulatory peptides

The invention relates to peptides derivatized with a hydrophilic polymer which, in some embodiments, bind to human FcRn and inhibit binding of the Fc portion of an IgG to an FcRn, thereby modulating serum IgG levels. The disclosed compositions and methods may be used in some embodiments, for example, in treating autoimmune diseases and inflammatory disorders. The invention also relates, in further embodiments, to methods of using and methods of making the peptides of the invention.

SYNTHESIS OF 8H-3A-AZA-CYCLOPENTA[A]INDENES AND 5,10-DIHYDROPYRROLO[1,2-B]ISOQUINOLINES DERIVATIVES AND THEIR USE AS ANTITUMOR THERAPEUTIC AGENTS

The present disclosure relates to a series of bis(hydroxymethyl) and its bis(carbamate) of 8H-3a-azacyclopenta[a]indene-1-yl and 5,10-dihydropyrrolo-[1,2-b]isoquinolines derivatives (Formula I-Formula IV) as DNA di-alkylating agents. The preliminary antitumor studies indicated that compounds disclosed herein could exhibit potent cytotoxicity in vitro and antitumor therapeutic efficacy in human tumor xenografts and could have little or no cross-resistance to either Taxol or Vinblastine. The results demonstrated that compounds disclosed herein possess potent antitumor therapeutic efficacy and are expected to have potential for clinical applications.

Synthesis and assay of isoquinoline derivatives as HIV-1 Tat-TAR interaction inhibitors

Four new isoquinoline derivatives bearing guanidinium group or amino group-terminated side chain were synthesized to target the HIV-1 TAR element. Their abilities to bind TAR RNA and inhibit Tat-TAR RNA interaction were determined by CE analysis, a Tat-dependent HIV-1 LTR-driven CAT assay and SIV-induced syncytium evaluation.

Synthesis and structure-activity relationships of potential anticonvulsants based on 2-piperidinecarboxylic acid and related pharmacophores

Using N-(2,6-dimethyl)phenyl-2-piperidinecarboxamide (1) and N-(α-methylbenzyl)-2-piperidinecarboxamide (2) as structural leads, a variety of analogues were synthesised and evaluated for anticonvulsant activity in the MES test in mice. In the N-benzyl series, introduction of 3-Cl, 4-Cl, 3,4-Cl2, or 3-CF3 groups on the aromatic ring led to an increase in MES activity. Replacement of the α-methyl group by either i-Pr or benzyl groups enhanced MES activity with no increase in neurotoxicity. Substitution on the piperidine ring nitrogen led to a decrease in MES activity and neurotoxicity, while reduction of the amide carbonyl led to a complete loss of activity. Movement of the carboxamide group to either the 3- or 4-positions of the piperidine ring decreased MES activity and neurotoxicity. Incorporation of the piperidine ring into a tetrahydroisoquinoline or diazahydrinone nucleus led to increased neurotoxicity. In the N-(2,6-dimethyl)phenyl series, opening of the piperidine ring between the 1- and 6-positions gave the active norleucine derivative 75 (ED50 = 5.8 mg kg-1, TD50 = 36.4 mg kg-1, PI = 6.3). Replacement of the piperidine ring of 1 by cycloalkane (cyclohexane, cyclopentane, and cyclobutane) resulted in compounds with decreased MES activity and neurotoxicity, whereas replacement of the piperidine ring by a 4-pyridyl group led to a retention of MES activity with a comparable PI. Simplification of the 2-piperidinecarboxamide nucleus of 1 into a glycinecarboxamide nucleus led to about a six-fold decrease in MES activity. The 2,6-dimethylanilides were the most potent compounds in the MES test in each group of compounds evaluated, and compounds 50 and 75 should be useful leads in the development of agents for the treatment of tonic-clonic and partial seizures in man.

Substituted quinoxaline-2-ones as glutamate receptor antagonists

A novel series of substituted quinoxaline 2-ones useful as neuroprotective agents are taught. Novel intermediates, processes of preparation, and pharmaceutical compositions containing the compounds are also taught. The compounds are glutamate receptor antagonists and are useful in the treatment of stroke, cerebral ischemia, or cerebral infarction resulting from thromboembolic or hemorrhagic stroke, cerebral vasospasms, hypoglycemia, cardiac arrest, status epilepticus, perinatal asphyxia, anoxia, seizure disorders, pain, Alzheimer's, Parkinson's, and Huntington's Diseases.

ANTITHROMBOTIC AGENTS

This invention relates to thrombin inhibiting compounds having the Formula IX--Y--NH--(CH 2) r--G I where X, Y, r and G have the values defined in the description, as well as pharmaceutical formulations containing those compounds and methods of their use as thrombin inhibitors, coagulation inhibitors, and thromboembolic disorder agents.

ANTITHROMBOTIC AGENTS

This invention relates to thrombin inhibiting compounds having the FormulaIX--Y--NH--(CH 2) r--G I where X, Y, r and G have the values defined in the description, as well as pharmaceutical formulations containing those compounds and methods of their use as thrombin inhibitors, coagulation inhibitors, and thromboembolic disorder agents.