22162-51-2

Usage

Uses

1. Used in Chemical Synthesis:
1-(2-Nitrobenzyl)pyrrole-2-carboxaldehyde is used as a precursor in the synthesis of various complex organic molecules, particularly those requiring the incorporation of the nitrobenzyl and pyrrole groups. Its unique structure allows for versatile reactivity in chemical reactions, making it a valuable component in the development of new compounds.
2. Used in Pharmaceutical Research:
1-(2-Nitrobenzyl)pyrrole-2-carboxaldehyde is used as a reagent in pharmaceutical research, where its properties may be exploited to develop new drug candidates. 1-(2-NITROBENZYL)PYRROLE-2-CARBOXALDEHYDE's reactivity and structural features could be harnessed to create novel therapeutic agents, particularly in the fields of medicinal chemistry and drug discovery.
3. Used in Material Science:
In material science, 1-(2-Nitrobenzyl)pyrrole-2-carboxaldehyde may be used as a component in the development of new materials with specific properties. Its incorporation into polymers or other materials could lead to the creation of materials with unique characteristics, such as improved stability, reactivity, or other desirable traits.
4. Used in Analytical Chemistry:
1-(2-Nitrobenzyl)pyrrole-2-carboxaldehyde can be employed as a reagent in analytical chemistry for the detection or quantification of specific compounds. Its distinctive chemical properties may enable the development of new analytical methods or the enhancement of existing ones, contributing to the advancement of chemical analysis techniques.

InChI:InChI=1/C12H10N2O3/c15-9-11-5-3-7-13(11)8-10-4-1-2-6-12(10)14(16)17/h1-7,9H,8H2

Upstream product

• 1003-29-8 2-pyrrole aldehyde 
• 612-23-7 2-nitrobenzyl chloride 
• 3958-60-9 2-nitrophenylmethyl bromide 
• 163915-96-6 (2-nitrophenyl)methyl methanesulfonate 

Downstream Products

• 22162-53-4 10,11-dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine 
• 168079-32-1 lixivaptan 
• 773868-91-0 1-[(2-nitrophenyl)methyl]pyrrole-2-carbinol 
• 220460-92-4 VNA-932 
• 168078-44-2 N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]-2,4-dichlorobenzamide 
• 168078-58-8 10,11-dihydro-10(4-nitrobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine 
• 168078-59-9 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine 
• 168079-42-3 10-[4-[(Diphenylphosphinyl)amino]benzoyl]-10,11-dihydro-5H-pyrrolo-[2,1-c][1,4]benzodiazepine 
• 168079-13-8 10,11-Dihydro-10-(4-nitrobenzoyl)-[3-(trifluoroacetyl)]-5H-pyrrolo[2,1-c][1,4]benzodiazepine 
• 168079-83-2 N-[4-(5H-Pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]tetrahydrofurane-2-carboxamide 
• 168080-03-3 N-[4-(5H-Pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]-2-(1H-[1,2,4]-triazol-1-yl)acetamide 

Relevant academic research and scientific papers

Preparation method 1 - (2 -nitrobenzyl) pyrrole -2 - formaldehyde

The invention discloses a preparation method of 1 - (2 -nitrobenzyl) pyrrole -2 - formaldehyde, which comprises the following steps: S1. 1 Nitrobenzene-based methanol, triethylamine and dichloromethane are added to the reaction kettle 2 - stirred at - 5 °

LIT-001, the First Nonpeptide Oxytocin Receptor Agonist that Improves Social Interaction in a Mouse Model of Autism

Oxytocin (OT) and its receptor (OT-R) are implicated in the etiology of autism spectrum disorders (ASD), and OT-R is a potential target for therapeutic intervention. Very few nonpeptide oxytocin agonists have currently been reported. Their molecular and in vivo pharmacology remain to be clarified, and none of them has been shown to be efficient in improving social interaction in animal models relevant to ASD. In an attempt to rationalize the design of centrally active nonpeptide full agonists, we studied in a systematic way the structural determinants of the affinity and efficacy of representative ligands of the V1a and V2 vasopressin receptor subtypes (V1a-R and V2-R) and of the oxytocin receptor. Our results confirm the subtlety of the structure-affinity and structure-efficacy relationships around vasopressin/oxytocin receptor ligands and lead however to the first nonpeptide OT receptor agonist active in a mouse model of ASD after peripheral ip administration.

An Improved, Scalable and Impurity-Free Process for Lixivaptan

An optimized synthetic method in high efficiency has been developed for the synthesis of lixivaptan from 2-nitrobenzyl bromide and pyrrole-2-carboxaldehyde. The byproducts among this procedure and an unknown impurity in crude product were investigated. The byproducts were speculated by 1H NMR or MS. The unknown impurity was characterized by 1H NMR, 13C NMR, and HRMS, confirming the structures as N-[3-chloro-4-(5H-pyrrolo[2,1-c][1,4]benzodiazepine-10(11H)-ylcarbonyl)phenyl]-N-(5-fluoro-2-methylbenzoyl)-5-fluoro-2-methylbenzamide. Afterwards, the impurity was synthesized to make comparisons. The target product lixivaptan was obtained with 47.6% overall yield and 99.93% purity. This cost-effective and environmentally friendly process is suitable for scale-up production.

DRUG DERIVATIVES

The present invention relates to derivatives of known active pharmaceutical compounds. These derivatives are differentiated from the parent active compound by virtue of being redox derivatives of the active compound. This means that one or more of the functional groups in the active compound has been converted to another group in one or more reactions which may be considered to represent a change of oxidation state. We refer to these compounds generally as redox derivatives. The derivatives of the invention may be related to the original parent active pharmaceutical compound by only a single step transformation, or may be related via several synthetic steps including one or more changes of oxidation state. In certain cases, the functional group obtained after two or more transformations may be in the same oxidation state as the parent active compound (and we include these compounds in our definition of redox derivatives). In other cases, the oxidation state of the derivative of the invention may be regarded as being different from that of the parent compound. In many cases, the compounds of the invention have inherent therapeutic activity on their own account. In some cases, this activity relative to the same target or targets of the parent compound is as good as or better than the activity which the parent compound has against the target or targets.

DRUG DERIVATIVES

The present invention relates to derivatives of known active pharmaceutical compounds. These derivatives are differentiated from the parent active compound by virtue of being redox derivatives of the active compound. This means that one or more of the functional groups in the active compound has been converted to another group in one or more reactions which may be considered to represent a change of oxidation state. We refer to these compounds generally as redox derivatives. The derivatives of the invention may be related to the original parent active pharmaceutical compound by only a single step transformation, or may be related via several synthetic steps including one or more changes of oxidation state. In certain cases, the functional group obtained after two or more transformations may be in the same oxidation state as the parent active compound (and we include these compounds in our definition of redox derivatives). In other cases, the oxidation state of the derivative of the invention may be regarded as being different from that of the parent compound. In many cases, the compounds of the invention have inherent therapeutic activity on their own account. In some cases, this activity relative to the same target or targets of the parent compound is as good as or better than the activity which the parent compound has against the target or targets.

5-Fluoro-2-methyl-N-[5-(5H-pyrrolo[2,1-c][1,4]benzodiazepine-10(11H)-yl carbonyl)-2-pyridinyl]benzamide (CL-385004) and analogs as orally active arginine vasopressin receptor antagonists

Synthesis and structure-activity relationships (SAR) of orally active arginine vasopressin (AVP) receptor antagonists are discussed. Potent and orally active AVP receptor antagonists are produced when ring A of VPA-985 (1) is replaced with a 3-pyridinyl unit (2b).