N-benzyl-3-formylbenzenesulfonamide | 213488-01-8

• 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: N-benzyl-3-formylbenzenesulfonamide
• 英文别名: N-benzyl-3-formyl-benzenesulfonamide
• CAS: 213488-01-8
• 化学式: C₁₄H₁₃NO₃S
• 分子量: 275.328
• InChiKey: IIYGPDZXOTYKRZ-UHFFFAOYSA-N

物化性质

• 沸点：
  473.1±55.0 °C(Predicted)
• 密度：
  1.296±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-benzyl-3-formylbenzenesulfonamide 在 盐酸 、 甲醇 、 sodium hydroxide 、 sodium tetrahydroborate 、 Amberlite IR-120 acidic resin 、 溶剂黄146 、 三苯基膦 、 lithium chloride 、 N,N'-diisopropyldiazene 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 51.0h， 生成
  参考文献：
  名称：

  β-Amino-thiols Inhibit the Zinc Metallopeptidase Activity of Tetanus Toxin Light Chain

  摘要：

  Tetanus neurotoxin is a 150-kDa protein produced by Clostridium tetani, which causes the lethal spastic paralytic syndromes of tetanus by blocking inhibitory neurotransmitter release at central synapses. The toxin light chain (50 kDa) has a zinc endopeptidase activity specific for synaptobrevin, an essential component of the neuroexocytosis apparatus. Previous unsuccessful attempts to block the proteolytic activity of this neurotoxin with well-known inhibitors of other zinc proteases led us to study the design of specific inhibitors as a possible drug therapy to prevent the progressive evolution of tetanus following infection. Starting from the synaptobrevin sequence at the level of the cleavage site by tetanus neurotoxin (Gln(76)-Phe(77)), a thiol analogue of glutamine demonstrated inhibitory activities in the millimolar range. A structure-activity relationship performed with this compound led us to determine the requirement for the correct positioning of the thiol group, the primary amino group, and a carboxamide or sulfonamide group on the side chain. This resulted in the design of a beta-amino-(4-sulfamoylphenyl)glycine-thiol, the first significantly efficient inhibitor of tetanus neurotoxin with a K-i value of 35 +/- 5 mu M.

  DOI：

  10.1021/jm981015z
• 作为产物：
  描述：

  N-Benzyl-3-hydroxymethyl-benzenesulfonamide 在 二氧化锰 氮 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以gave the title compound (317 mg, 85%) as a white solid的产率得到N-benzyl-3-formylbenzenesulfonamide
  参考文献：
  名称：

  Chemokine receptor binding heterocyclic compounds

  摘要：

  含有多种杂环芳基取代基的三级胺可用作趋化因子受体调节剂。

  公开号：

  US07312234B2

文献信息

• Redox-Neutral and Atom-Economic Route to β-Carbolines via Gold-Catalyzed [4 + 2] Cycloaddition of Indolylynamides and Cyanamides
  作者：Nikolay V. Shcherbakov、Elena I. Chikunova、Dmitry Dar’in、Vadim Yu. Kukushkin、Alexey Yu. Dubovtsev

  DOI：10.1021/acs.joc.1c02119

  日期：2021.12.17

  Gold(I)-catalyzed [4 + 2] cycloaddition of indolylynamides and cyanamides (aminonitriles) is an efficient redox-neutral and atom-economic route to diversely substituted 1,3-diamino-β-carbolines. The protocol operates under mild conditions (Ph3PAuNTf2 5 mol %, DCE, 60 °C) with a good tolerance to functional groups (23 examples and yields up to 98%). The obtained β-carboline systems represent a versatile

  金 (I) 催化的 [4 + 2] 吲哚胺和氰胺（氨基腈）环加成是一种有效的氧化还原中性和原子经济途径，可制备多种取代的 1,3-二氨基-β-咔啉。该协议在温和的条件下运行（Ph 3 PAuNTf 2 5 mol%，DCE，60 °C），对官能团具有良好的耐受性（23 个示例，产量高达 98%）。获得的 β-咔啉系统代表了一个多功能合成平台，具有可修饰的取代基，用于连续功能化。对照实验表明反应物的性质和所用催化剂的特性在发展的环加成反应中的关键作用。
• [EN] PYRAZOLO[4,3-D]PYRIMIDINES AS KINASE INHIBITORS<br/>[FR] PYRAZOLO[4,3-D]PYRIMIDINES UTILES EN TANT QU'INHIBITEURS DE KINASES
  申请人：ORIGENIS GMBH

  公开号：WO2014060112A1

  公开（公告）日：2014-04-24

  The present invention relates to novel compounds of formula (I) that are capable of inhibiting one or more kinases, especially SYK (Spleen Tyrosine Kinase), LRRK2 (Leucine-rich repeat kinase 2) and/or MYLK (Myosin light chain kinase) or mutants thereof. The compounds find applications in the treatment of a variety of diseases. These diseases include autoimmune diseases, inflammatory diseases, bone diseases, metabolic diseases, neurological and neurodegenerative diseases, cancer, cardiovascular diseases, allergies, asthma, alzheimer's disease, parkinson's disease, skin disorders, eye diseases, infectious diseases and hormone-related diseases.

  本发明涉及具有式（I）的新化合物，其能够抑制一个或多个激酶，特别是SYK（脾酪氨酸激酶）、LRRK2（富含亮氨酸重复的激酶2）和/或MYLK（肌球蛋白轻链激酶）或其突变体。这些化合物可用于治疗多种疾病。这些疾病包括自身免疫疾病、炎症性疾病、骨疾病、代谢性疾病、神经和神经退行性疾病、癌症、心血管疾病、过敏、哮喘、阿尔茨海默病、帕金森病、皮肤疾病、眼部疾病、传染病和激素相关疾病。
• CHEMOKINE RECEPTOR BINDING HETEROCYCLIC COMPOUNDS
  申请人：Bridger Gary

  公开号：US20080090846A1

  公开（公告）日：2008-04-17

  Tertiary amines containing a multiplicity of heteroaromatic substituents are useful as chemokine receptor modulators.

  含有多种杂环芳基取代基的三级胺可用作趋化因子受体调节剂。
• PYRAZOLO[4,3-D]PYRIMIDINES AS KINASE INHIBITORS
  申请人：ORIGENIS GMBH

  公开号：US20150266882A1

  公开（公告）日：2015-09-24

  The present invention relates to novel compounds of formula (I) that are capable of inhibiting one or more kinases, especially SYK (Spleen Tyrosine Kinase), LRRK2 (Leucine-rich repeat kinase 2) and/or MYLK (Myosin light chain kinase) or mutants thereof. The compounds find applications in the treatment of a variety of diseases. These diseases include autoimmune diseases, inflammatory diseases, bone diseases, metabolic diseases, neurological and neurodegenerative diseases, cancer, cardiovascular diseases, allergies, asthma, alzheimer's disease, parkinson's disease, skin disorders, eye diseases, infectious diseases and hormone-related diseases.

  本发明涉及化合物(I)的新型化合物，能够抑制一个或多个激酶，特别是SYK（脾酪氨酸激酶）、LRRK2（富含亮氨酸重复的激酶2）和/或MYLK（肌球蛋白轻链激酶）或其突变体。这些化合物在治疗多种疾病方面有应用。这些疾病包括自身免疫疾病、炎症性疾病、骨病、代谢性疾病、神经和神经退行性疾病、癌症、心血管疾病、过敏、哮喘、阿尔茨海默病、帕金森病、皮肤疾病、眼病、传染病和激素相关疾病。
• US6835731B2
  申请人：——

  公开号：US6835731B2

  公开（公告）日：2004-12-28