4-Hydrazinobenzeneacetonitrile hydrochloride

• 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-Hydrazinobenzeneacetonitrile hydrochloride
• 英文别名: 4-(cyanomethylphenyl)hydrazine hydrochloride；4-cyanomethylphenylhydrazine hydrochloride；4-hydrazinobenzyl cyanide hydrochloride；(4-hydrazinophenyl)acetonitrile hydrochloride；4-hydrazino phenylacetonitrile hydrochloride；Benzeneacetonitrile, 4-hydrazinyl-, hydrochloride (1:1)；2-(4-hydrazinylphenyl)acetonitrile;hydrochloride
• 化学式: C₈H₉N₃*ClH
• 分子量: 183.64
• InChiKey: OOYLNHYKZWRIHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.46
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  61.8
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Hydrazinobenzeneacetonitrile hydrochloride 在 sodium hydroxide 、 硫酸 作用下， 以 乙醇 为溶剂， 反应 20.0h， 生成 N,N-dimethyl-2-(5-(carbethoxymethyl)-1H-indol-3-yl)ethylamine
  参考文献：
  名称：

  Improved Fischer Indole Reaction for the Preparation of N,N-Dimethyltryptamines: Synthesis of L-695,894, a Potent 5-HT1D Receptor Agonist

  摘要：

  DOI：

  10.1021/jo00092a046
• 作为产物：
  描述：

  对氨基苯乙腈 在 盐酸 、 tin(ll) chloride 、 sodium nitrite 作用下， 生成 4-Hydrazinobenzeneacetonitrile hydrochloride
  参考文献：
  名称：

  5-（恶二唑基）色胺的合成和血清素能活性：5-HT1D受体的有效激动剂。

  摘要：

  描述了一系列新的5-（恶二唑基）色胺的合成和5-HT1D受体活性。研究了恶二唑3-取代基的修饰，连接链的长度（n）和胺取代基，并揭示了5-HT1D受体域中的大结合口袋。容纳恶二唑取代基如苄基而不会损失激动剂的效力或功效。在苯基或苄基间隔基团上引入极性官能团会导致亲和力和功能效能提高10倍。当杂环与吲哚偶联时，观察到最佳的5-HT1D活性，苄基磺酰胺20t和20u代表了一些已知的最有效的5-HT1D激动剂。杂环中的S取代O导致效能进一步提高。删除恶二唑N-2不会降低活性，建议在此位置仅需要一个H键受体。讨论了这些化合物对5-HT1D受体相对于其他血清素能受体的选择性。磺酰胺20t对5-HT1D的选择性比5-HT2、5-HT1C和5-HT3受体高> 1000倍，对5-HT1A受体的选择性高10倍。研究了该系列化合物的功能活性，并证明了与5-HT相当的5-HT1D受体效能和功效。

  DOI：

  10.1021/jm00063a003

文献信息

• Triazole containing indole derivatives
  申请人：Merck Sharp & Dohme Limited

  公开号：US05298520A1

  公开（公告）日：1994-03-29

  A class of substituted imidazole, triazole and tetrazole derivatives are selective agonists of 5-HT.sub.1 -like receptors and are therefore useful in the treatment of clinical conditions, in particular migraine and associated disorders, for which a selective agonist of these receptors is indicated.

  一类取代的咪唑、三唑和四唑衍生物是5-HT.sub.1 -样受体的选择性激动剂，因此在治疗临床疾病中特别有用，尤其是偏头痛和相关的紊乱，对于这些疾病，需要使用这些受体的选择性激动剂。
• [EN] PDK-1/AKT SIGNALING INHIBITORS<br/>[FR] INHIBITEURS DE SIGNALISATION PDK-1/AKT
  申请人：UNIV OHIO STATE RES FOUND

  公开号：WO2005044130A1

  公开（公告）日：2005-05-19

  A new class of phosphoinositide-dependent kinase-1 (PDK-1) inhibitors of formula (I): wherein X is selected from the group consisting of alkyl and haloalkyl; Ar is an aryl radical selected from the group consisting of phenyl, biphenyl, naphthyl, anthryl, phenanthryl, and fluorenyl; and wherein Ar is optionally substituted with one or more radicals selected from the group consisting of halo, C1 C4 alkyl, C1 C4 haloalkyl, azido, C1 C4 azidoalkyl, aryl, akylaryl, haloaryl, haloalkylaryl, and combinations thereof; and R is selected from the group consisting of nitrile, acetonitrile, ethylnitrile, propylnitrile, carboxamide, amidine, tetrazole, oxime, hydrazone, acetamidine, aminoacetamide, guanidine, and urea. Also provided are methods of using the compounds for the treatment and prevention of cancer in humans.

  一种新的磷脂酰肌醇依赖性激酶-1（PDK-1）抑制剂的化学式（I）：其中X选自烷基和卤代烷基组成的群体；Ar是从苯基、联苯基、萘基、蒽基、菲基组成的基团中选取的芳基基团；其中Ar可选择地被一个或多个从卤素、C1-C4烷基、C1-C4卤代烷基、叠氮化物、C1-C4叠氮基烷基、芳基、烷基芳基、卤代芳基、卤代烷基芳基等组成的基团取代；R选自腈、乙腈、乙腈、丙腈、羧酰胺、胺基、四唑、肟、醛肟、乙酰胺、氨基乙酰胺、胍、尿素等组成的群体。还提供了使用这些化合物用于人类癌症的治疗和预防的方法。
• ANTI-INFECTIVE AGENTS AGAINST INTRACELLULAR PATHOGENS
  申请人：Chen Ching-Shih

  公开号：US20090111799A1

  公开（公告）日：2009-04-30

  A new class of phosphoinositide-dependent kinase-1 (PDK-1) inhibitors of Formula I: wherein X wherein X is —CF 3 , Ar is selected from and R is selected from where R′ is L-Lys, D-Lys, β-Ala, L-Lue, L-Ile, Phe, SO 2 CH 2 CH 2 NH 2 , SO 2 NH 2 , Asn, Glu or Gyl, and R″ is methyl, ethyl, allyl, CH 2 CH 2 OH, CH 2 CN, CH 2 CH 2 CN, CH 2 CONH 2 ,

  一种新的磷脂酰肌醇依赖激酶-1（PDK-1）抑制剂的化学式I：其中X为—CF3，Ar从中选择，R从中选择，其中R′为L-赖氨酸，D-赖氨酸，β-丙氨酸，L-亮氨酸，L-异亮氨酸，苯丙氨酸，SO2CH2CH2NH2，SO2NH2，天冬氨酸，谷氨酸或甘氨酸，R″为甲基，乙基，烯丙基，CH2CH2OH，CH2CN，CH2CH2CN，CH2CONH2。
• Indole-5-acetamides for treatment of migraine
  申请人：Glaxo Group Limited

  公开号：US04650810A1

  公开（公告）日：1987-03-17

  Compounds are disclosed of general formula (I): ##STR1## wherein R.sub.1, R.sub.3, R.sub.4, R.sub.6 and R.sub.7, which may be the same or different, each represents a hydrogen atom or an alkyl group; R.sub.2 represents a hydrogen atom or an alkyl, aryl, aralkyl, cycloalkyl or alkenyl group; or R.sub.1 and R.sub.2, together with the nitrogen atom to which they are attached, form a saturated monocyclic 5 to 7-membered ring which may optionally contain a further hetero function; R.sub.5 represents a hydrogen atom or an alkyl or alkenyl group; or R.sub.4 and R.sub.5 together form an aralkylidene group; Alk represents an alkylene chain containing two or three carbon atoms which may be unsubstituted or substituted by not more than two C.sub.1-3 alkyl groups; and X represents an oxygen or sulphur atom; and physiologically acceptable salts, solvates and bioprecursors thereof. The compounds are described as potentially useful for the treatment of migraine and may be formulated as pharmaceutical compositions in conventional manner using one or more pharmaceutically acceptable carriers or excipients. Various processes for the preparation of the compounds are disclosed including, for example, a process involving reacting an indole having an appropriate nitrile group at the 5-position, with a suitable oxygen- or sulphur-containing compound in order to introduce the required amide or thioamide group at the 5-position on the indole nucleus.

  本发明涉及一般式(I)的化合物：其中R.sub.1、R.sub.3、R.sub.4、R.sub.6和R.sub.7，可以相同也可以不同，分别代表氢原子或烷基基团；R.sub.2代表氢原子或烷基、芳基、芳基烷基、环烷基或烯基基团；或者R.sub.1和R.sub.2与它们连接的氮原子一起形成一个饱和的单环5到7成员环，该环可能还含有另外的杂原子功能基团；R.sub.5代表氢原子或烷基或烯基基团；或者R.sub.4和R.sub.5一起形成芳基烷基亚甲基基团；Alk代表一个含有两个或三个碳原子的烷基链，该链可以未被取代或被不超过两个C.sub.1-3烷基基团取代；X代表氧原子或硫原子；以及其生理上可接受的盐、溶剂化合物和生物前体。所述化合物被描述为治疗偏头痛的潜在有用化合物，并且可以以传统方式制备为含有一种或多种医药上可接受的载体或赋形剂的药物组合物。公开了制备这些化合物的各种方法，例如，涉及将具有适当的5-位置上的腈基团的吲哚与适当的含氧或硫化合物反应以在吲哚核上引入所需的酰胺或硫酰胺基团的过程。
• Carboxymethylated pyridoindole antioxidants as aldose reductase inhibitors: Synthesis, activity, partitioning, and molecular modeling
  作者：Milan Stefek、Vladimir Snirc、Paul-Omer Djoubissie、Magdalena Majekova、Vassilis Demopoulos、Lucia Rackova、Zelmira Bezakova、Cimen Karasu、Vincenzo Carbone、Ossama El-Kabbani

  DOI：10.1016/j.bmc.2008.03.039

  日期：2008.5

  reductase was determined by measuring the corresponding inhibitory activities. Antioxidant action of the novel compounds was documented in a DPPH test and in a liposomal membrane model, oxidatively stressed by peroxyl radicals. The presence of a basicity center at the tertiary nitrogen, in addition to the acidic carboxylic function, predisposes these compounds to form double charged zwitterionic species

  从有效的六氢吡啶并吲哚抗氧化剂斯托巴定开始，合成了一系列羧甲基化的四氢和六氢吡啶并吲哚衍生物，并测试了其对醛糖还原酶的抑制作用，醛糖还原酶是一种涉及糖尿病并发症病因的酶。用常规方法测定大鼠晶状体醛糖还原酶的体外抑制作用。（2-苄基-2,3,4,5-四氢-1H-吡啶并[4,3-b]吲哚-8-基）-乙酸（5b）和（2-苯乙基-2,3， 4,5-四氢-1H-吡啶并[4,3-b]吲哚-8-基）-乙酸（5c）是该系列中最有效的化合物，其活性在微摩尔范围内，显示出无竞争性的抑制作用。除了酸性功能的重要性之外，当比较四氢和六氢吡啶并吲哚同类物时，亲脂性芳香族主链的空间构象对抑制效果有很大影响。通过测量相应的抑制活性来确定相对紧密相关的醛还原酶的选择性。新化合物的抗氧化作用已在DPPH测试和脂质体膜模型中得到证明，它们被过氧自由基氧化应激。除酸性羧酸官能团外，在叔氮上还存在碱性中心，这使这些化合物易于形成