3,3-dimethyl succinic anhydride | 1079340-44-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3,3-dimethyl succinic anhydride
• CAS: 1079340-44-5
• 化学式: C₁₂H₁₈O₇
• 分子量: 274.271
• InChiKey: QLWKRXYSQKSILB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.06
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  117.97
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3,3-dimethyl succinic anhydride 、 羽扇豆醇 在 吡啶 、 4-二甲氨基吡啶 作用下， 以70%的产率得到3{beta}-O-(3',3'-dimethylsuccinyl)lupeol
  参考文献：
  名称：

  Synthesis of new heterocyclic lupeol derivatives as nitric oxide and pro-inflammatory cytokine inhibitors

  摘要：

  A series of heterocyclic derivatives including indoles, pyrazines along with oximes and esters were synthesized from lupeol and evaluated for anti-inflammatory activity through inhibition of lipopolysaccharide (LPS) induced nitric oxide (NO) production in RAW 264.7 and J774A.1 cells. All the synthesized molecules of lupeol were found to be more active in inhibiting NO production with an IC50 of 18.4-48.7 mu M in both the cell lines when compared to the specific nitric oxide synthase (NOS) inhibitor, L-NAME (IC50 = 69.21 and 73.18 mu M on RAW 264.7 and J774A.1 cells, respectively). The halogen substitution at phenyl ring of indole moiety leads to potent inhibition of NO production with half maximal concentration ranging from 18.4 to 41.7 mu M. Furthermore, alkyl (11, 12) and p-bromo/iodo (15, 16) substituted compounds at a concentration of 20 mu g/mL exhibited mild inhibition (29-42%) of LPS-induced tumor necrosis factor alpha (TNF-alpha) and weak inhibition (10-22%) towards interleukin 1-beta (IL-1 beta) production in both the cell lines. All the derivatives were found to be non-cytotoxic when tested at their IC50 (mu M). These findings suggest that the derivatives of lupeol could be a lead to potent inhibitors of NO. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.05.032

文献信息

• Synthesis and in vivo evaluation of new steviol derivatives that protect against cardiomyopathy by inhibiting ferroptosis
  作者：Chao Xu、E Ou、Zhiyin Li、Zhenyu Chen、Qi Jia、Xiaojia Xu、Liping Luo、Geng Xu、Jiansong Liu、Zhengqiang Yuan、Yu Zhao

  DOI：10.1016/j.bioorg.2022.106142

  日期：2022.12

  discover new agents for CVDs treatment, 30 derivatives of steviol, including 22 new ones, were synthesized, and evaluated their protective activity in vivo using the doxorubicin (DOX) induced zebrafish cardiomyopathy model. Our results firstly demonstrated that steviol has promising cardioprotective activity and further modification of steviol can greatly improve the activity. Among the new derivatives

  心血管疾病 (CVD) 仍然是全球死亡的主要原因。抑制铁死亡从而预防心肌细胞死亡是预防和治疗心肌病的一种有前途且有效的策略。甜菊醇是一种对-贝壳杉烯二萜类化合物，具有广谱生物活性。在本研究中，为了发现治疗心血管疾病的新药物，合成了 30 种甜菊醇衍生物，包括 22 种新衍生物，并使用多柔比星 (DOX) 诱导的斑马鱼心肌病模型评估了它们的体内保护活性。我们的结果首先表明甜菊醇具有良好的心脏保护活性，进一步修饰甜菊醇可以大大提高活性。在新的衍生品中，16d和16e显示最有效的活动。16d (1 μM) 和16e (0.1 μM)均可有效维持斑马鱼的正常心脏形状并防止 DOX 损害的心脏功能障碍。其疗效远优于母体天然产物甜菊醇和阳性药物左西孟旦。进一步的研究表明，16d和16e通过抑制谷胱甘肽消耗、铁积累和脂质过氧化，减少活性氧过度积累，恢复线粒体膜电位，从而抑制 DOX 诱导的铁死亡，从而保
• Synthesis and proteasome inhibition of glycyrrhetinic acid derivatives
  作者：Li Huang、Donglei Yu、Phong Ho、Keduo Qian、Kuo-Hsiung Lee、Chin-Ho Chen

  DOI：10.1016/j.bmc.2008.05.078

  日期：2008.7

  This study discovered that glycyrrhetinic acid inhibited the human 20S proteasome at 22.3 mu M. Esterification of the C-3 hydroxyl group on glycyrrhetinic acid with various carboxylic acid reagents yielded a series of analogs with marked improved potency. Among the derivatives, glycyrrhetinic acid 3-O-isophthalate (17) was the most potent compound with IC50 of 0.22 mu M, which was approximately 100-fold more potent than glycyrrhetinic acid. (c) 2008 Elsevier Ltd. All rights reserved.
• Triterpene based compounds with potent anti-maturation activity against HIV-1
  作者：David Gerrish、In Chul Kim、Dange V. Kumar、Harry Austin、Jennifer E. Garrus、Vijay Baichwal、Michael Saunders、Rena S. McKinnon、Mark B. Anderson、Robert Carlson、Esther Arranz-Plaza、Kraig M. Yager

  DOI：10.1016/j.bmcl.2008.10.098

  日期：2008.12

  Efforts towards developing orally bioavailable HIV-1 maturation inhibitors starting from betulinic acid 1 are described. SAR resulted in improved potency, physicochemical properties, and enhanced oral absorption in rats. (C) 2008 Elsevier Ltd. All rights reserved.