4-isopropoxy-3-nitrobenzaldehyde | 125872-99-3

• 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-isopropoxy-3-nitrobenzaldehyde
• 英文别名: 3-nitro-4-propan-2-yloxybenzaldehyde
• CAS: 125872-99-3
• 化学式: C₁₀H₁₁NO₄
• mdl: MFCD10690722
• 分子量: 209.202
• InChiKey: UXEDVOJZLGKYHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-isopropoxy-3-nitrobenzaldehyde 在 盐酸 、 重铬酸吡啶 、 4 A molecular sieve 、 铁粉 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 17.5h， 生成 (3-amino-4-isopropoxy-phenyl)-(3,4,5-trimethoxy-phenyl)-methanone
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of 3-Aminobenzophenones as Antimitotic Agents

  摘要：

  A new series of 3-aminobenzophenone compounds as potent inhibitors of tubulin polymerization was discovered based on the mimic of the aminocombretastatin molecular skeleton. Lead compounds 5 and 11, with alkoxy groups at the C-4 position of B-ring, were potent cytotoxic agents and inhibitors of tubulin polymerization through the binding to the colchicine-binding site of tubulin. The corresponding antitubulin activities of 5 and 11 were similar to or greater than combretastatin A-4 and AVE-8063. Replacement of the methoxy group with a chloro group in the B ring of aminobenzopheneones (3, 8, and 9) caused drastic decrease in cytotoxic and antitubulin activity except in compounds 4 and 10, which could result from a unique alignment between chloro and amino groups located at the para position to each other. SAR information revealed that introduction of an amino group at the C-3 position in B ring of benzophenones, in addition to a methoxy group at the C-4 position, plays an important role for maximal cytotoxicity.

  DOI：

  10.1021/jm0305974
• 作为产物：
  描述：

  (4-isopropoxy-3-nitrophenyl)methanol 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 以89%的产率得到4-isopropoxy-3-nitrobenzaldehyde
  参考文献：
  名称：

  基于苯甲酰脲支架的两亲性α-螺旋模拟物† ‡

  摘要：

  两亲分子的设计与合成。 苯甲酰脲描述了α-螺旋模拟物。这些构象受限的分子允许疏水和亲水基团进行正确的角度和空间投影，因此可以在α-螺旋的两个面上复制侧链。

  DOI：

  10.1039/c2ob25273b

文献信息

• Benzoxazepinones and their use as squalene synthase inhibitors
  申请人：——

  公开号：US20030078251A1

  公开（公告）日：2003-04-24

  There is disclosed a compound represented by the formula [I]: 1 wherein R 1 is optionally substituted 1-carboxyethyl group, optionally substituted alkyl-sulfonyl group, optionally substituted (carboxy-cycloalkyl)-alkyl group, —X 1 —X 2 —Ar—X 3 —X 4 —COOH (wherein X 1 and X 4 are a bond or alkylene group, X 2 and X 3 are a bond, —O—, —S—, Ar is divalent aromatic group etc.), R 2 is alkyl group optionally substituted with alkanoyloxy group and/or hydroxy group, R 3 is alkyl group, and W is halogen atom, etc., or a salt thereof. The compound has the cholesterol lowering activity and the triglyceride lowering activity and is useful for preventing and/or treating hyperlipidemia.

  披露了一种由公式[I]表示的化合物： 1 其中R 1 是可选地取代的1-羧乙基，可选地取代的烷基亚磺酰基，可选地取代的(羧基环烷基)-烷基，—X 1 —X 2 —Ar—X 3 —X 4 —COOH(其中X 1 和X 4 是键或亚烷基，X 2 和X 3 是键，—O—，—S—，Ar是二价芳香族等)，R 2 是可选地由酰氧基和/或羟基取代的烷基，R 3 是烷基，W是卤素原子等，或其盐。该化合物具有降低胆固醇活性和降低甘油三酯活性，用于预防或治疗高脂血症。
• Synthesis and structure-activity relationships of N - (3 - (1H-imidazol-2-yl) phenyl) - 3-phenylpropionamide derivatives as a novel class of covalent inhibitors of p97/VCP ATPase
  作者：Ke Wang、Lianguo Chen、Xinyan Dai、Zi Ye、Chuan Zhou、Chong-Jing Zhang、Zhiqiang Feng

  DOI：10.1016/j.ejmech.2023.115094

  日期：2023.2

  Noncovalent inhibitors of p97 have entered clinical studies. Compared with noncovalent inhibitors, covalent inhibitors have unique advantages in maintaining inhibitory effect and improving the resistance of the target. We previously employed the activity-based protein profiling to definitely identify p97 as the protein target of FL-18 that has a unique scaffold of benpropargylamide coupled with an

  p97的非共价抑制剂已进入临床研究。与非共价抑制剂相比，共价抑制剂在维持抑制效果、提高靶点耐药性方面具有独特的优势。我们之前使用基于活性的蛋白质分析来确定 p97 作为 FL-18 的蛋白质靶标，FL-18 具有独特的苯丙酰胺与咪唑偶联的支架。在这项研究中，我们报告了涉及新支架的彻底的结构-活性-关系研究。总共三轮优化发现了迄今为止最有效的 p97 共价抑制剂。化学蛋白质组学研究表明，新合成的化合物仍然针对 p97 的 C522 残基，并在复杂的整个蛋白质组中保留了选择性。这项研究提供了一套新的 p97 共价抑制剂，以协助其生物学研究和药物发现。
• N-Benzyl-3-sulfonamidopyrrolidines as novel inhibitors of cell division in E. coli
  作者：Shubhasish Mukherjee、Carolyn A. Robinson、Andrew G. Howe、Tali Mazor、Peter A. Wood、Sameer Urgaonkar、Alan M. Hebert、Debabrata RayChaudhuri、Jared T. Shaw

  DOI：10.1016/j.bmcl.2007.09.010

  日期：2007.12

  A new small molecule inhibitor of bacterial cell division has been discovered using a high-throughput screen in Escherichia coli. Although the lead screening hit (534F6) exhibited modest inhibition of the GTPase activity of FtsZ (20 +/- 5% at 100 mu M of compound), a primary target for bacterial cell division inhibitors, several analogs caused potent bacterial growth inhibition with negligible antagonism of FtsZ GTPase activity. A library of analogs has been prepared and several alkyne-tagged photo-affinity probes have been synthesized for use in experiments to elucidate the primary target of this compound. (c) 2007 Elsevier Ltd. All rights reserved.
• BENZOXAZEPINONES AND THEIR USE AS SQUALENE SYNTHASE INHIBITORS
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP1292585A1

  公开（公告）日：2003-03-19
• US4948796A
  申请人：——

  公开号：US4948796A

  公开（公告）日：1990-08-14