O-(3-iodobenzyl)hydroxylamine | 854383-01-0

• 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-(3-iodobenzyl)hydroxylamine
• 英文别名: O-[(3-iodophenyl)methyl]hydroxylamine
• CAS: 854383-01-0
• 化学式: C₇H₈INO
• 分子量: 249.051
• InChiKey: ULWJONMSUDEJFR-UHFFFAOYSA-N

物化性质

• 沸点：
  328.4±35.0 °C(Predicted)
• 密度：
  1.806±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 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-(3-iodobenzyl)hydroxylamine 在 盐酸 、 sodium cyanoborohydride 作用下， 以 乙醇 为溶剂， 反应 1.5h， 生成 N-isopropyl-O-(3-iodobenzyl)-hydroxylamine
  参考文献：
  名称：

  A simple and efficient method to label l-fucose

  摘要：

  This letter reports a new labeling method of fucoidan and more precisely of its monomer, L-fucose. We studied the coupling processes of new aryliodide precursors to L-fucose in order to prepare the next step, that is, the fucoidan radiolabeling. The use of precursors containing hydrazide and hydroxylamines is an alternative procedure avoiding the use of toxic borohydride or organic borane used for reductive amination. These coupling reactions are efficient and stereoselective. They provide stable products. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.07.047
• 作为产物：
  描述：

  3-碘苯甲醇 在 一水合肼 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 18.0h， 生成 O-(3-iodobenzyl)hydroxylamine
  参考文献：
  名称：

  A simple and efficient method to label l-fucose

  摘要：

  This letter reports a new labeling method of fucoidan and more precisely of its monomer, L-fucose. We studied the coupling processes of new aryliodide precursors to L-fucose in order to prepare the next step, that is, the fucoidan radiolabeling. The use of precursors containing hydrazide and hydroxylamines is an alternative procedure avoiding the use of toxic borohydride or organic borane used for reductive amination. These coupling reactions are efficient and stereoselective. They provide stable products. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.07.047

文献信息

• 4-Alkyloxyimino-cytosine nucleotides: tethering approaches to molecular probes for the P2Y6 receptor
  作者：P. Suresh Jayasekara、Matthew O. Barrett、Christopher B. Ball、Kyle A. Brown、Eszter Kozma、Stefano Costanzi、Lucia Squarcialupi、Ramachandran Balasubramanian、Hiroshi Maruoka、Kenneth A. Jacobson

  DOI：10.1039/c3md00132f

  日期：——

  4-Alkyloxyimino derivatives of pyrimidine nucleotides display high potency as agonists of certain G protein-coupled P2Y receptors (P2YRs). In an effort to functionalize a P2Y6R agonist for fluorescent labeling, we probed two positions (N4 and γ-phosphate of cytidine derivatives) with various functional groups, including alkynes for click chemistry. Functionalization of extended imino substituents at the 4 position of the pyrimidine nucleobase of CDP preserved P2Y6R potency generally better than γ-phosphoester formation in CTP derivatives. Fluorescent Alexa Fluor 488 conjugate 16 activated the human P2Y6R expressed in 1321N1 human astrocytoma cells with an EC50 of 9 nM, and exhibited high selectivity for this receptor over other uridine nucleotide-activated P2Y receptors. Flow cytometry detected specific labeling with 16 to P2Y6R-expressing but not to wild-type 1321N1 cells. Additionally, confocal microscopy indicated both internalized 16 (t1/2 of 18 min) and surface-bound fluorescence. Known P2Y6R ligands inhibited labeling. Theoretical docking of 16 to a homology model of the P2Y6R predicted electrostatic interactions between the fluorophore and extracellular portion of TM3. Thus, we have identified the N4-benzyloxy group as a structurally permissive site for synthesis of functionalized congeners leading to high affinity molecular probes for studying the P2Y6R.

  4-烷氧亚氨基嘧啶核苷酸衍生物作为某些G蛋白偶联P2Y受体（P2YRs）的激动剂显示出高度效力。为了对P2Y6R激动剂进行荧光标记，我们在两个位置（胞苷衍生物的N4位和γ-磷酸基团）上探查了包括炔烃在内的各种功能团，用于点击化学反应。在CDP的嘧啶核碱4位上进行扩展亚氨基取代，相比于CTP衍生物中的γ-磷酸酯形成，通常更好地保持了P2Y6R的效力。荧光染料Alexa Fluor 488的共轭物16激活了在1321N1人星形胶质瘤细胞中表达的人P2Y6R，其EC50为9 nM，并且对这种受体的选择性远高于其他由尿嘧啶核苷酸激活的P2Y受体。流式细胞术检测到16对表达P2Y6R的细胞有特异性标记，而对野生型1321N1细胞无标记。此外，共聚焦显微镜显示16被内化（半衰期18分钟）并有表面结合的荧光。已知的P2Y6R配体抑制标记。16与P2Y6R的同源模型的理论对接预测了荧光团与TM3的外部部分之间的静电相互作用。因此，我们确定了N4-苄氧基团作为合成功能化类似物的结构容许位点，从而得到用于研究P2Y6R的高亲和力分子探针。
• 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
• COUMPOUNDS AND METHODS FOR INHIBITING THE INTERACTION OF BCL PROTEINS WITH BINDING PARTNERS
  申请人：Infinity Discovery, Inc.

  公开号：EP1768966B1

  公开（公告）日：2012-03-07