N-(hexyl)sulfamide | 42731-64-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫酸及其衍生物
• 英文名称: N-(hexyl)sulfamide
• 英文别名: N-hexylsulfamide；1-(sulfamoylamino)hexane
• CAS: 42731-64-6
• 化学式: C₆H₁₆N₂O₂S
• 分子量: 180.271
• InChiKey: TVXGEUUCQIEWFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  80.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-氯苯基)-2,4-二氧代丁酸乙酯 、 N-(hexyl)sulfamide 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 96.0h， 以59%的产率得到3-(4-chlorophenyl)-2-hexyl-1,1-dioxo-1,2-dihydro-1^λ6-1,2,6-thiadiazine-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  Discovery of 1,1-dioxo-1,2,6-thiadiazine-5-carboxamide derivatives as cannabinoid-like molecules with agonist and antagonist activity

  摘要：

  A series of new 2-substituted 1,1-dioxo-1,2,6-thiadiazine-5-carboxylate derivatives have been prepared from monosubstituted sulfamides in order to obtain N-substituted1,1-dioxo-1,2,6-thiadiazine-5-carboxamides as novel cannabinoid derivatives, analogues of Rimonabant (SR141716A). Their potential functional activity on cannabinoid receptors has been evaluated in vitro and in vivo in mice, showing that two compounds (37 and 39) behave as cannabinoid agonists in vitro. Their potency is lower than that of the reference compound, WIN 55,212-2, but their efficacy is similar to that of this cannabinoid agonist, although no in vivo activity is observed. Another derivative (38) behaves as a cannabinoid antagonist both in vitro and in vivo, being its efficacy and potency similar to that of the well-known antagonist SR141716A. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.07.056
• 作为产物：
  描述：

  tert-butyl N-hexylsulfamoylcarbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以86%的产率得到N-(hexyl)sulfamide
  参考文献：
  名称：

  Synthesis of arabinose glycosyl sulfamides as potential inhibitors of mycobacterial cell wall biosynthesis

  摘要：

  A series of arabinose glycosyl sulfamides with varying alkyl chain types and lengths were synthesised as mimics of decaprenolphosphoarabinose (DPA), and as potential inhibitors of mycobacterial cell wall biosynthesis. Unprecedented conversion of the desired furanose to the thermodynamically more stable pyranose form occurred during final de-protection. Biological testing against Mycobacterium smegmatis revealed low to moderate anti-mycobacterial activity with marked dependence on alkyl chain length, which in the case of mono-substituted sulfamides was maximal for a C-10 chain. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.07.050

文献信息

• Novel Non-carboxylate Benzoylsulfonamide-Based Protein Tyrosine Phosphatase 1B Inhibitors with Non-competitive Actions
  作者：Ko Morishita、Yoshimichi Shoji、Shunkichi Tanaka、Masaki Fukui、Yuma Ito、Tatsuya Kitao、Shin-ichiro Ozawa、Shuichi Hirono、Hiroaki Shirahase

  DOI：10.1248/cpb.c17-00635

  日期：——

  A novel series of benzoylsulfonamide derivatives were synthesized and biologically evaluated. Among them, 4-(biphenyl-4-ylmethylsulfanylmethyl)-N-(hexane-1-sulfonyl)benzamide (compound 18K) was identified as a protein tyrosine phosphatase 1B (PTP1B) inhibitor with potent and selective inhibitory activity against PTP1B (IC50=0.25 µM). Compound 18K functioned as a non-competitive inhibitor and bound

  合成了一系列新颖的苯甲酰基磺酰胺衍生物，并对其进行了生物学评估。其中，4-（联苯基-4-基甲基硫烷基甲基）-N-（己烷-1-磺酰基）苯甲酰胺（化合物18K）被鉴定为对酪氨酸磷酸酶1B（PTP1B）有抑制作用的蛋白酪氨酸磷酸酶（IC50 = 0.25 µM）。化合物18K充当非竞争性抑制剂并与PTP1B的变构位点结合。它还在小鼠（最大药物浓度（Cmax）= 30,5 mg / kg时为45.5 µM），大鼠（Cmax = 30 mg / kg，Cmax = 53.6 µM）和小猎犬（10 mg / kg时Cmax = 37.8 µM）中具有较高的口服吸收率。公斤/天），并以30 mg / kg / d（每os（po））的血浆葡萄糖水平显着降低了一周，在db / db小鼠中没有副作用。综上所述，
• Basicity of nitrogen–sulphur(<scp>VI</scp>) compounds. Part 6. Ionization of NN′-di-and N-mono-substituted sulphamides and dihydro-2,1,3-benzothiadiazoline and benzothiadiazine 2,2-dioxides (cyclic sulphamides)
  作者：Padraig O. Burke、Séan D. McDermott、Thomas J. Hannigan、William J. Spillane

  DOI：10.1039/p29840001851

  日期：——

  tri-substituted sulphamides have been synthesised and their ionization equilibria in base (Schemes 1–3) have been studied. Many of the sulphamides are new materials. The pKa values obtained for each series have been correlated in Hammett and Taft plots. The Hammett ρ values obtained for the ionization of the proximate hydrogen are ca. 2.3. The Taft ρ* value obtained for ionization of the ‘remoter’

  已合成了36个二取代的，单取代的和两个三取代的磺酰胺，并研究了它们在碱中的电离平衡（方案1-3）。许多磺酰胺是新材料。在Hammett和Taft图中，已将每个系列获得的p K a值关联起来。对于邻近氢的电离获得的哈米特ρ值约为。2.3。用于“远程”氢离子化获得的Taftρ*值为1.68。六元环状磺酰胺比其无环类似物的酸性大约高出约2。2.5 p ķ一个单元和五元环sulphamides是CA。4 p K a单元比模型开放链对应单元酸性更高。硫d-轨道参与和环应变被认为是这种“增强酸”作用的可能来源。
• BENZIMIDAZOLE DERIVATIVES
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP1142880A1

  公开（公告）日：2001-10-10

  The present invention provides novel benzimidazole derivatives of the following formula (I) and salts thereof: wherein R1 represents a lower alkyl group or a lower alkyloxy-lower alkyl group: R2 represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group, and such; R3 represents a lower alkyl group, a lower alkenyl group, an aryl group, a lower alkylaryl group, an aryl-lower alkenyl group, a halothienyl group, a lower alkylamino group, or an aryl-lower alkylamino group; A represents a benzene ring, a naphthalene ring, or a pyridine ring; and X represents a halogen atom. The derivatives and their salts have blood sugar level-depressing activity or PDE5-inhibiting activity, and are useful as pharmaceutical preparations.

  本发明提供了下式(I)的新型苯并咪唑衍生物及其盐类： 其中 R1 代表低级烷基或低级烷氧基-低级烷基：R2代表氢原子、卤素原子、具有1至8个碳原子的烷基、芳基等；R3代表低级烷基、低级烯基、芳基、低级烷芳基、芳基-低级烯基、卤代噻吩基、低级烷氨基或芳基-低级烷氨基；A代表苯环、萘环或吡啶环；X代表卤素原子。这些衍生物及其盐类具有降低血糖水平的活性或 PDE5 抑制活性，可用作药物制剂。
• CYCLIC AMINE COMPOUND
  申请人：Daiichi Sankyo Company, Limited

  公开号：EP2036896B1

  公开（公告）日：2012-03-14
• Morishita, Ko; Shoji, Yoshimichi; Tanaka, Shunkichi, Chemical and pharmaceutical bulletin, 2017, vol. 65, # 12, p. 1144 - 1160
  作者：Morishita, Ko、Shoji, Yoshimichi、Tanaka, Shunkichi、Fukui, Masaki、Ito, Yuma、Kitao, Tatsuya、Shirahase, Hiroaki、Ozawa, Shin-Ichiro、Hirono, Shuichi

  DOI：——

  日期：——