4-iodophenyl chloroformate | 1312010-00-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-iodophenyl chloroformate
• 英文别名: (4-iodophenyl) carbonochloridate
• CAS: 1312010-00-6
• 化学式: C₇H₄ClIO₂
• 分子量: 282.465
• InChiKey: NZTZBFBNLVJVLS-UHFFFAOYSA-N

物化性质

• 沸点：
  267.0±23.0 °C(Predicted)
• 密度：
  1.961±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-iodophenyl chloroformate 、 5-羟基色胺盐酸盐 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以43%的产率得到4-iodophenyl N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]carbamate
  参考文献：
  名称：

  New N-Arachidonoylserotonin Analogues with Potential “Dual” Mechanism of Action against Pain

  摘要：

  N-Arachidonoylserotonin (AA-5-HT, 1a) is an inhibitor of fatty acid amide hydrolase (FAAH) that acts also as an antagonist of transient receptor potential vanilloid-type 1 (TRPV1) channels and is analgesic in rodents. We modified the chemical structure of 1a with the aim of developing "hybrid" FAAH/TRPV1 blockers more potent than the parent compound or obtaining analogues with single activity at either of the two targets to study the mechanism of the analgesic action of 1a. Thirty-eight AA-5-HT analogues, containing a serotonin "head" bound to a variety of lipophilic moieties via amide, urea, or carbamate functionalities, were synthesized. Unlike 1a, most of the new compounds possessed activity at only one of the two considered targets. The amides 1b and 1c of alpha- and gamma-linolenic acid, however, showed "hybrid" activity similar to 1a. The carbarnate 3f (OMDM 106), although unable to antagonize TRPV1 receptors, was the most potent FAAH inhibitor in this study (IC50 = 0.5 mu M). Compounds 3f and 1m (OMDM129), which exhibited activity at only FAAH or TRPV1, respectively, were 10-fold less potent than 1a at preventing formal in-induced hyperalgesia in mice.

  DOI：

  10.1021/jm070678q
• 作为产物：
  描述：

  光气 、 4-碘苯酚 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 4-iodophenyl chloroformate
  参考文献：
  名称：

  New N-Arachidonoylserotonin Analogues with Potential “Dual” Mechanism of Action against Pain

  摘要：

  N-Arachidonoylserotonin (AA-5-HT, 1a) is an inhibitor of fatty acid amide hydrolase (FAAH) that acts also as an antagonist of transient receptor potential vanilloid-type 1 (TRPV1) channels and is analgesic in rodents. We modified the chemical structure of 1a with the aim of developing "hybrid" FAAH/TRPV1 blockers more potent than the parent compound or obtaining analogues with single activity at either of the two targets to study the mechanism of the analgesic action of 1a. Thirty-eight AA-5-HT analogues, containing a serotonin "head" bound to a variety of lipophilic moieties via amide, urea, or carbamate functionalities, were synthesized. Unlike 1a, most of the new compounds possessed activity at only one of the two considered targets. The amides 1b and 1c of alpha- and gamma-linolenic acid, however, showed "hybrid" activity similar to 1a. The carbarnate 3f (OMDM 106), although unable to antagonize TRPV1 receptors, was the most potent FAAH inhibitor in this study (IC50 = 0.5 mu M). Compounds 3f and 1m (OMDM129), which exhibited activity at only FAAH or TRPV1, respectively, were 10-fold less potent than 1a at preventing formal in-induced hyperalgesia in mice.

  DOI：

  10.1021/jm070678q

文献信息

• [EN] BENZOAZOLYPIPERAZINE DERIVATIVES HAVING MGLUR1- AND MGLUR5-ANTAGONISTIC ACTIVITY<br/>[FR] DERIVES DE BENZOAZOLYLPIPERAZINE PRESENTANT UNE ACTIVITE ANTAGONISTE VIS-A-VIS DE MGLUR1 ET DE MGLUR5
  申请人：EURO CELTIQUE SA

  公开号：WO2004058754A1

  公开（公告）日：2004-07-15

  A compound of formula (I) wherein Ar1, A, R3, x, and m are as disclosed herein and Ar2 is a benzothiazolyl, benzooxazolyl, or benzoimidazolyl group or a pharmaceutically acceptable salt thereof (a “Benzoazolylpiperazine Compound”), compositions comprising a Benzoazolylpiperazine Compound, and methods for treating or preventing pain, UI, an ulcer, IBD, IBS, an addictive disorder, Parkinson’s disease, parkinsonism, anxiety, epilepsy, stroke, a seizure, a pruritic condition, psychosis, a cognitive disorder, a memory deficit, retricted brain function, Huntington’s chorea, amyotrophic lateral sclerosis, dementia, retinopathy, a muscle spasm, a migraine, vomiting, dyskinesia, or depression in an animal comprising administering to an animal in need thereof an effective amount of Benzoazolylpiperazine Compound are disclosed.

  公式（I）的化合物，其中Ar1，A，R3，x和m如本文所述，Ar2是苯并噻唑基，苯并噁唑基或苯并咪唑基或其药学上可接受的盐（“苯并咪唑基哌嗪化合物”），包含苯并咪唑基哌嗪化合物的组合物，并且揭示了治疗或预防疼痛，UI，溃疡，IBD，IBS，成瘾障碍，帕金森病，帕金森综合症，焦虑，癫痫，中风，癫痫发作，瘙痒症，精神病，认知障碍，记忆力缺失，受限的脑功能，亨廷顿舞蹈症，肌萎缩性侧索硬化症，痴呆症，视网膜病变，肌肉痉挛，偏头痛，呕吐，运动失调或抑郁症的方法，包括向需要治疗的动物中投与有效量的苯并咪唑基哌嗪化合物。
• Bifunctional cytotoxic agents containing the CTI pharmacophore
  申请人：Pfizer Inc.

  公开号：US10870706B2

  公开（公告）日：2020-12-22

  The present invention is directed to novel bifunctional CTI-CTI and CBI-CTI dimers of the formula: F1-L1-T-L2-F2 where F1, L1, T, L2 and F2 are as defined herein, useful for the treatment for proliferative diseases, where the inventive dimers can function as stand-alone drugs, payloads in antibody-drug-conjugates (ADCs), and linker-payload compounds useful in connection with the production or administration of such ADCs; and to compositions including the aforementioned dimers, linker-payloads and ADCs, and methods for using these dimers, linker-payloads and ADCs, to treat pathological conditions including cancer.

  本发明涉及式中的新型双功能 CTI-CTI 和 CBI-CTI 二聚体： F1-L1-T-L2-F2 其中F1、L1、T、L2和F2如本文所定义，可用于治疗增殖性疾病，本发明的二聚体可作为独立药物、抗体-药物共轭物（ADC）中的有效载荷以及与生产或施用此类ADC有关的连接体-有效载荷化合物；以及包括上述二聚体、连接体-载荷和 ADC 的组合物，以及使用这些二聚体、连接体-载荷和 ADC 治疗包括癌症在内的病理状况的方法。
• Synthesis of radioiodinated probes targeted toward matrix metalloproteinase-12
  作者：Masayori Hagimori、Takashi Temma、Shinji Kudo、Kohei Sano、Naoya Kondo、Takahiro Mukai

  DOI：10.1016/j.bmcl.2017.11.027

  日期：2018.1

  Matrix metalloproteinase-12 (MMP-12, macrophage elastase) is a member of the MMP family that is responsible for the degradation of extracellular matrix, and is associated with the inflammatory process of chronic obstructive pulmonary disease (COPD). COPD, characterized by progressive and irreversible airflow obstruction, is recently a major cause of mortality and morbidity worldwide. Herein, to develop radioiodinated probes for the early diagnosis of COPD, we designed and synthesized novel MMP-12-targeted dibenzofuran compounds (1-3) with a variety of linker structures (carbamate, amide, and sulfonamide). In competitive enzyme activity assays, it was revealed that the linker structures significantly affected the inhibitory activity against and selectivity for MMP-12. Compound 1, with carbamate linker, demonstrated potent MMP-12 inhibitory activity (IC50 = 8.5 nM) compared to compound 2, with amide linker, and compound 3, with sulfonamide linker. Using bromo-substituted carbamate 13 as a radioiodination precursor, [I-125] 1 was successfully prepared to high radiochemical purity (over 98%) and good specific radioactivity (4.1 GBq/mu mol). These results suggest that radioiodinated compound 1 is potent as a novel MMP-12-targeted probe. (C) 2017 Elsevier Ltd. All rights reserved.
• US9598410B2
  申请人：——

  公开号：US9598410B2

  公开（公告）日：2017-03-21