O-(2-iodobenzyl)hydroxylamine | 854383-00-9

• 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: O-(2-iodobenzyl)hydroxylamine
• 英文别名: O-[(2-iodophenyl)methyl]hydroxylamine
• CAS: 854383-00-9
• 化学式: C₇H₈INO
• 分子量: 249.051
• InChiKey: WHDWMOWZTKOQRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  O-(2-iodobenzyl)hydroxylamine 在 盐酸 作用下， 以 乙醚 为溶剂， 生成 邻碘苄氧胺盐酸盐
  参考文献：
  名称：

  O-alkylhydroxylamines as rationally-designed mechanism-based inhibitors of indoleamine 2,3-dioxygenase-1

  摘要：

  Indoleamine 2,3-dioxygenase-1 (IDO1) is a promising therapeutic target for the treatment of cancer, chronic viral infections, and other diseases characterized by pathological immune suppression. Recently important advances have been made in understanding IDO1's catalytic mechanism. Although much remains to be discovered, there is strong evidence that the mechanism proceeds through a heme-iron bound alkylperoxy transition or intermediate state. Accordingly, we explored stable structural mimics of the alkylperoxy species and provide evidence that such structures do mimic the alkylperoxy transition or intermediate state. We discovered that O-benzylhydroxylamine, a commercially available compound, is a. potent sub-micromolar inhibitor of IDO1. Structure activity studies of over forty derivatives of O-benzylhydroxylamine led to further improvement in inhibitor potency, particularly with the addition of halogen atoms to the meta position of the aromatic ring. The most potent derivatives and the lead, O-benzylhydroxylamine, have high ligand efficiency values, which are considered an important criterion for successful drug development. Notably, two of the most potent compounds demonstrated nanomolar-level cell-based potency and limited toxicity. The combination of the simplicity of the structures of these compounds and their excellent cellular activity makes them quite attractive for biological exploration of IDO1 function and antitumor therapeutic applications. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.12.028
• 作为产物：
  描述：

  O-(2-iodobenzyl)-N-hydroxyphthalimide 在 一水合肼 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以97%的产率得到O-(2-iodobenzyl)hydroxylamine
  参考文献：
  名称：

  碘化聚（ε-己内酯）X射线不透明材料的肟官能化策略

  摘要：

  由于X射线摄影和计算机断层扫描（CT）是两种最常见的人体成像技术，因此研究人员致力于开发可生物降解和生物相容的聚合物分子，以替代传统的小分子造影剂。本报告重点介绍了通过肟“点击”连接反应合成新型可生物降解的碘化聚（ε-己内酯）共聚物。通过锡（II）介导的开环聚合反应，然后进行后聚合脱保护步骤，可制得一系列含酮材料。预期的X射线不透明性是通过用碘化羟胺对所得聚合物进行酸催化的肟后聚合修饰而赋予的。使用质子核磁共振（NMR）对所有小分子和高分子材料进行表征，以确保纯度，官能团化学计量和数均分子量计算。此外，用凝胶渗透色谱法（GPC）评估聚合物，以确定聚合物样品的多分散性和一般的分子量分布形状，并通过差示扫描量热法（DSC）和热重分析（TGA）评估其热性能。©2015 Wiley Periodicals，Inc. J. Polym。科学，A部分：Polym。化学2015年，53，2421至2430年

  DOI：

  10.1002/pola.27706

文献信息

• BIODEGRADABLE POLYESTER- AND POLY(ESTER AMIDE) BASED X-RAY IMAGING AGENTS
  申请人：Clemson University

  公开号：US20150290344A1

  公开（公告）日：2015-10-15

  Biodegradable, radio-opaque polyesters and poly(ester amides) are described herein. The polyesters contain a plurality of radio-opaque agents or radio-opaque agent-containing moieties that are covalently bound along or from the polymer backbone. The agents/moieties may be bound to the termini of the polymer provided they are bound within the polyester backbone as well. The polyester can be aliphatic or aromatic. The polyester and poly(ester amide) is substituted with a plurality of radio-opaque graft agents or prepared from an appropriate radio-opaque monomer agent. The materials can be used for any application where a radio-opaque material is desired or necessary. The materials can be used to form, in whole or in part, a medical device, or coating thereon or therein.

  本文介绍了可生物降解、放射性不透明的聚酯和聚酯酰胺。聚酯中含有多种放射性不透明剂或含有这些剂的官能团，这些剂/官能团沿着或从聚合物骨架上共价结合。这些剂/官能团可以结合到聚合物的末端，只要它们也在聚酯骨架内结合。聚酯可以是脂肪族或芳香族的。聚酯和聚酯酰胺被多种放射性不透明的嫁接剂取代或由适当的放射性不透明单体剂制备而成。这些材料可用于任何需要放射性不透明材料的应用。这些材料可用于制造医疗器械的整体或部分，或用于其内部或外部的涂层。
• In-chain functionalization through the combination of ring opening copolymerization and oxime “Click” reaction towards X-ray opaque polylactide copolymers
  作者：Wenhuan Wang、Lin Sang、Weizong Kong、Yiping Zhao、Zhiyong Wei、Yang Li

  DOI：10.1016/j.cclet.2019.04.062

  日期：2020.2

  Abstract X-ray imaging functionalization of biodegradable polyesters is a great demand and challenge in biomedical applications. In this work, a strategy of in-chain functionalization through the combination of ring opening copolymerization and oxime “Click” postfunctionalization was developed towards X-ray opaque polylactide copolymers. A functionalized cyclic carbonate was first synthesized and used

  摘要生物可降解聚酯的X射线成像功能化在生物医学应用中是一个巨大的需求和挑战。在这项工作中，针对X射线不透明的聚丙交酯共聚物，开发了通过开环共聚和肟“ Click”后官能化相结合的链内官能化策略。首先合成了官能化的环状碳酸酯，并将其用作聚丙交酯共聚物的共聚单体，将其进行肟“点击”反应后官能化为碘化聚丙交酯共聚物。追踪并确认了目标产物的化学结构和物理性质。Alamar蓝用3T3-Swiss albino进行的体外细胞毒性评估显示出较低的细胞毒性。通过Micro-CT分析X射线的射线不透性，并通过Hounsfield单位值进行量化，可以根据原料进行定制。它是在生物医学应用中有希望的X射线可见的可植入生物材料。
• Novel Hydroxamic Acid Esters and Pharmaceutical Use Thereof
  申请人：Fensholdt Jef

  公开号：US20070244117A1

  公开（公告）日：2007-10-18

  The invention relates to compounds of general formula I wherein D, E, F, G, W, Y, R 1 , A, R 9 , X, B, R 8 are as defined herein, and pharmaceutically acceptable salts, hydrates, or solvates thereof, for use—alone or in combination with one or more other pharmaceutically active compounds—in therapy, for treating diseases associated with deregulated angiogenesis, such as cancer.

  本发明涉及一般式I的化合物，其中D、E、F、G、W、Y、R1、A、R9、X、B、R8如本文所定义，并且其药学上可接受的盐、水合物或溶剂化物，用于治疗与异常血管生成相关的疾病，如癌症，可单独使用或与一个或多个其他药理活性化合物联合使用。
• IDO Inhibitors
  申请人：Mautino Mario

  公开号：US20110053941A1

  公开（公告）日：2011-03-03

  Presently provided are methods for (a) modulating an activity of indoleamine 2,3-dioxygenase comprising contacting an indoleamine 2,3-dioxygenase with a modulation effective amount of a compound as described in one of the aspects described herein; (b) treating indoleamine 2,3-dioxygenase (IDO) mediated immunosuppression in a subject in need thereof, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (c) treating a medical conditions that benefit from the inhibition of enzymatic activity of indoleamine-2,3-dioxygenase comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (d) enhancing the effectiveness of an anti-cancer treatment comprising administering an anti-cancer agent and a compound as described in one of the aspects described herein; (e) treating tumor-specific immunosuppression associated with cancer comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; and (f) treating immunosuppression associated with an infectious disease, e.g., HIV-I infection, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount a compound as described in one of the aspects described herein.

  目前提供以下方法：(a) 通过接触本文中描述的化合物的调节有效量与吲哚胺2,3-二氧化酶相互作用，从而调节吲哚胺2,3-二氧化酶的活性；(b) 治疗需要吲哚胺2,3-二氧化酶(IDO)介导的免疫抑制的患者，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(c) 治疗需要抑制吲哚胺-2,3-二氧化酶酶活性的医疗状况，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(d) 增强抗癌治疗的有效性，包括给予抗癌剂和本文中描述的化合物；(e) 治疗与癌症相关的肿瘤特异性免疫抑制，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(f) 治疗与传染病相关的免疫抑制，例如HIV-1感染，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量。
• HYDROXAMIC ACID ESTERS AND PHARMACEUTICAL USE THEREOF
  申请人：LEO PHARMA A/S

  公开号：EP1697312B1

  公开（公告）日：2011-07-20